1181:(HOFs) are porous organic materials that are connected by non-covalent interactions such as hydrogen bonds and π-π interactions. However, due to the relatively weak strength of hydrogen bonds, HOFs rarely exhibit permanent porosity upon removal of solvent molecules. Nonetheless, the weak interactions in HOFs allow the formation of single crystals, which are more amenable to crystallographic studies compared to COFs. Second, HOFs can be easily regenerated through dissolution and recrystallization due to their weak interactions. In 2016, Seferos et al. reported the synthesis of HOFs from chalcogen heterocycles capped with N-methyliminodiacetic acid (MIDA) boronates which contain both hydrogen bond donors and acceptors. MIDA-capped thiophene, selenophene, and tellurophenes were synthesized through
1013:, since the emission maxima shifted to longer wavelengths with increasing solvent polarity. Through DFT calculations, the authors was found that the HOMO was localized on the π-orbitals of the tellurophene and the electron-donating substituent, with the LUMO localized over the π*-orbitals of the tellurophene and the electron-withdrawing substituent. It was concluded that having both electron-donating and electron-withdrawing substituents stabilizes the LUMO, with the HOMO-LUMO transitions having significant charge-transfer character, which in turn explained the solvatochromic effect. This work therefore showed how one can tune the
1048:
narrow polydispersity, the authors investigated the optimal conditions using kinetic studies and DFT calculations. It was found experimentally that the branched side chain played an important role on the polymerization rate and polymer quality. To mitigate this effect, monomers with various other side chains were synthesized. From this, it was found that moving the ethyl branches away from the heterocycle to the more remote 3- and 4- positions led to an improved polymerization rate and control, such that P3ATe with narrow
886:(mCPBA). Through DFT calculations, it was found that upon oxidation of PT, the resulting Te(IV) oxide PT-O had a lower HOMO level, with the LUMO being significantly stabilized. This led to a large decrease in the HOMO-LUMO energy gap, which predicted a red shift in the maxima of the absorption spectrum. Furthermore, it was found that the electron density of the LUMO included a Te-O σ* orbital. This orbital picture has been further reproduced using Avogadro and GAMESS, as shown on the orbital diagram below.
973:-B, was found to be non-emissive, indicating that the Te(II) center in B-Te-B plays an important role in phosphorescence. By replacing the pinacolboronate esters with thiophenes, there was no luminescence, indicating that both Te(II) and BPin played a cooperative role leading to emission. DFT calculations on B-Te-B revealed that the HOMO has significant contribution from the lone pair on the Te p-orbital, with the LUMO being significantly delocalized over the B-C bond. Furthermore, the energy of the
1146:
961:
1081:(OFETs), it was found that the selenophene polymer had the highest charge mobility, and that the tellurium analogue did not lead to an increase in mobility despite the larger size of tellurium, and possibility of closer interchain Te-Te interactions, which was attributed to the low solubility of P3TeV which resulted in poor film formation. Therefore, the authors remarked that future work entailed modifying the side-chains to increase solubility.
906:, it was found that the yellow solid that had formed as the product had a downfield shift at 1123.3 ppm upon addition of mCPBA. NMR spectra and the absorption spectrum of the product in solution led to the authors attributing this product as the telluroxide. Upon addition of a large excess of mCPBA (8 equiv), the solution became bright yellow, which slowly diminished upon stirring overnight. The final product was an insoluble white solid (TeO
1021:
890:
683:
37:
872:
1060:
46:
1171:
1090:
24:
952:. The proposed mechanism was where the first equivalent of mCPBA forms the selenoxide, with the extra three equivalents reacting with selenophene to produce a selenone diepoxide intermediate. This mechanism was consistent with the formation of telluroxide upon addition of mCPBA, and the formation of an ene-dione product upon addition of 4 equivalents of mCPBA.
808:
1158:, with the terminal CH carbon of the alkyne attaching to the boron. Consistent with this observation, it was proposed that the Te and B act as a FLP, undergoing a cyclcoaddition to the alkyne such that the boron adds to the CH carbon, due to the steric bulk at the boron center. In 2018, this FLP chemistry was developed further through the synthesis of 4
918:
993:
596:
969:
reported phosphorescent materials made of expensive rare metals such as iridium and platinum. The phosphorescence was found to be aggregation-induced, as the tellurophene was non-emissive when dissolved in THF, but glowed bright green in the solid state and upon aggregation in THF/water solutions. A dibrominated Te(IV) tellurophene, B-TeBr
502:
738:
578:
541:
475:
408:
372:
754:, the authors was found that the two strongest optical transitions for PT was the HOMO to LUMO and HOMO to LUMO+1 transitions. Upon addition of halogen, however, it was found that the HOMO-LUMO energy gap decreased, with the LUMO possessing significant Te-X antibonding character. Because of this, it was postulated that by filling the
650:) of 310 ± 20 L mol, and would also bind Br and BzO. Using computational studies, it was found that an ethynylene linkage between two tellurophenes would place the chalcogen bond donors at an appropriate distance such that the receptor could form two chalcogen bonds with the chloride. Through sequential
1130:, and pseudo-tetrahedral, respectively. The C-C bond length was observed to be 1.326(4) Å, much longer than a C-C triple bond and closer to a C-C double bond, indicating that the compound had activated phenylacetylene through FLP chemistry. However, unlike other reported FLP compounds, it was unable to activate H
843:) resulted in a red-shifted absorption peak at 435 nm in the UV-vis spectrum, with a peak appearing at 280 nm with a concomitant decrease of the peak at 435 nm upon treatment with excess peroxide. Through studying the reaction rate, it was found that the reaction was first order in both H
968:
Compared to thiophenes, tellurophenes have been found to have lower optical band gaps, significantly lower LUMO levels, and higher charge carrier mobilities. In 2014, Rivard et al. reported the phosphorescence of pinacolboronate-substituted tellurophenes at room temperature, in contrast to previously
897:
Addition of 1 equiv of mCPBA to a solution of PT led to an immediate colour change from colourless to yellow. However, upon adding more mCPBA (4 equiv), there was a gradual decrease in the absorbance at 388 nm and a resulting absorption increase below 300 nm. As one would expect a red shift
758:
with electrons, this would facilitate breaking of the Te-X bond, and hence, halogen dissociation. And indeed, upon addition of excess halogen, the peak at 342 nm corresponding to the tellurophene decreased, while a red-shifted absorption peak appeared, with the peak being more red-shifted as one
733:
character. It was postulated that the low quantum yields were due to the fact that there were no lower energy excited states with Te-X antibonding character, and that this would limit the efficiency of the reaction. Therefore, it was thought that by changing the substituents on tellurophene such that
673:
calculations which showed that the minimum-energy geometry was one where the chloride anion was in between the tellurium atoms, with Te–Cl bond distances of 3.23 Å and Cl–Te–C angles of 170°. One significant difference of the bidentate receptor was that there was no anion-arene
391:
at 20 °C. This method could be generalised to prepare 2,5-derivatives of tellurophene by selecting a suitably-substituted diacetylene precursor. The product was obtained as a pale yellow liquid with a melting and boiling point of −36 °C and 148 °C, respectively. Taticchi et al.
745:
In 2015, Seferos et al. demonstrated that 2,5-diphenyltellurophene (PT) could participate in photoreductive elimination of fluorine, chlorine, and bromine via the two-electron Te(IV)/Te(II) photocycle, with quantum yields of up to 16.9%. This was the first report of an organotellurium compound that
1047:
CTP is an important route to synthesize polymers with a narrow molecular weight distribution and a well defined end-group, but it was found in 2013 that applying CTP-conditions for the synthesis of P3ATe led to polymers with low molecular weights, and broad polydispersities. To obtain P3ATe with a
1153:
Later, Stephan et al. reported the synthesis of various Te-B heterocycles through reaction of 1-bora-4-tellurocyclohexa-2,5-diene and two equivalents of a terminal alkyne upon heating, with loss of a diarylalkyne. X-ray crystal studies revealed that the C-C bond distances in the heterocycle were
509:
However, metal-catalyzed cross-coupling reactions to synthesize 3-functionalized tellurophenes were deemed to be cumbersome as they required 3-bromo- or 3-iodo-tellurophenes, the syntheses of which could be quite complicated. An alternative method was reported by
Seferos et al. in 2013, but this
1117:
at room temperature, affording bright orange crystals in 94% yield. It was found through B NMR that the product had a four-coordinate boron, which indicated a weak Te-B interaction due to the broad signal. Reacting this compound with phenylacetylene at room temperature resulted in a
1056:. Furthermore, it was found that upon moving the branching point away from the heterocycle led to a red-shift in the optical absorption, which was attributed to a decrease in the degree of twisting, resulting in an increase in the conjugation between the tellurophene backbone.
1000:
In 2018, Okuma et al. reported the synthesis of various 2,5-diaryltellurophenes substituted with electron-donating and electron-withdrawing groups through sequential ditelluride exchange and intramolecular cyclization reactions. By having both electron-donating (e.g.
734:
the main transition upon photoexcitation would be HOMO to LUMO, this would significantly improve the reaction by removing efficiency losses through relaxations from states that did not possess Te-X antibonding character and did not promote Te-X bond dissociation.
867:
Ag/AgCl), it was found that its absorption peak decreased with the concurrent increase of the peak at 354 nm corresponding to the diaryltellurophene. This process could be reversed upon applying a potential of 0.8 V, thus indicating reversible oxidation.
1076:
and a polydispersity of 2.4. By synthesizing thiophene and selenophene analogues, it was found that there was a reduction in the optical band gap as a result of the stabilization of the LUMO, resulting in a small band gap of 1.4 eV for P3TeV. By constructing
1035:, where it was found that the HOMO and LUMO orbitals were in qualitative agreement with the orbital pictures reported by Okuma, showing that the HOMO and LUMO show extensive orbital delocalization on the p-anisyl and p-cyanophenyl substituents, respectively.
1189:(PXRD) that DPTe-MIDA had lower crystallinity compared to DPT-MIDA and DPSe-MIDA. However, the main diffraction peaks of DPTe-MIDA were similar to those of DPT-MIDA and DPSe-MIDA, suggesting that all three frameworks self-assembled into similar structures.
929:, the authors investigated the formation of singlet oxygen upon irradiation of PT. Upon irradiation of a solution containing both PT and 9,10-DPA with white light, a decrease in the absorbance at 355 nm was observed, which was indicative of O
1193:(TGA) revealed that acetonitrile molecules are removed at around 150 °C for DPT-MIDA and DPSe-MIDA, and 70 °C for DPTe-MIDA, with all three HOFs decomposing above 350 °C. DPT-MIDA had the highest surface area, as found by CO
1067:
Heeney et al. reported the synthesis of the first tellurophene-vinylene copolymer through Stille coupling of 2,5-dibromo-3-dodecyltellurophene and (E)-1,2-bis(tributylstannyl)ethylene, resulting in P3TeV in 57% yield with an approximate
1888:
Schmidt, Michael W.; Baldridge, Kim K.; Boatz, Jerry A.; Elbert, Steven T.; Gordon, Mark S.; Jensen, Jan H.; Koseki, Shiro; Matsunaga, Nikita; Nguyen, Kiet A. (November 1993). "General atomic and molecular electronic structure system".
2239:
He, Gang; Torres
Delgado, William; Schatz, Devon J.; Merten, Christian; Mohammadpour, Arash; Mayr, Lorenz; Ferguson, Michael J.; McDonald, Robert; Brown, Alex (2014-03-25). "Coaxing Solid-State Phosphorescence from Tellurophenes".
1138:, which was attributed to the fact that telluroethers are poor nucleophiles. Although the telluroether did not undergo oxidation by halogens to produce the corresponding Te(IV) dihalide compounds, it was found to react with
654:
reactions, an ethynylene-linked bistellurophene was synthesized from 2-iodo-5-(perfluorophenyl)tellurophene. Upon addition of Cl to a solution of the receptor in THF, changes to the absorption spectrum were found showing a
989:), which was proposed to lead to efficient singlet-triplet crossing to occur, leading to emission. This was in contrast to the sulfur and selenium analogues, where the triplet state was found to be ~1 eV higher in energy.
1677:
Jahnke, Ashlee A.; Djukic, Brandon; McCormick, Theresa M.; Buchaca
Domingo, Ester; Hellmann, Christoph; Lee, Yunjeong; Seferos, Dwight S. (2013). "Poly(3-alkyltellurophene)s Are Solution-Processable Polyheterocycles".
2321:
Nagahora, Noriyoshi; Yahata, Shuhei; Goto, Shoko; Shioji, Kosei; Okuma, Kentaro (2018-02-02). "2,5-Diaryltellurophenes: Effect of
Electron-Donating and Electron-Withdrawing Groups on their Optoelectronic Properties".
423:
studies. It has been found that the Te–C bond has a length of 2.046 Å, which is longer than that of selenophene. Further, the C–Te–C angle has been determined to be 82°, smaller than that found in
1971:
Carrera, Elisa I.; McCormick, Theresa M.; Kapp, Marius J.; Lough, Alan J.; Seferos, Dwight S. (2013-11-19). "Thermal and
Photoreductive Elimination from the Tellurium Center of π-Conjugated Tellurophenes".
1185:. Crystal structures of DPT-MIDA and DPSe-MIDA showed the presence of C-H⋯O hydrogen bonding and C-H⋯π interactions. DPTe-MIDA was not amenable to crystallographic analysis, and it was found through
791:, however, it was found that there were significant decomposition products owing to the halogen's high reactivity towards PT. This was circumvented by using water as a halogen trap instead of DMBD (
364:
mixture, was obtained in 56% yield, and found to appear as yellow-orange crystals with a melting point of 239-239.5 °C. The same compound was obtained from 1,4-diiodotetraphenylbutadiene and
787:
sample with a 447.5 nm lamp, it was found that the absorption spectrum of the sample rapidly changed back to that of PT in 12 seconds. This was also observed using H NMR spectroscopy. With F
705:
from an isoindigo-substituted tellurophene, 2,5-bistellurophene. Due to the extensive π-conjugation which resulted in low-energy absorption, relatively low-energy light (505 nm) was used to
521:
for the synthesis of a variety of functionalized tellurophenes without the use of transition metals. This was done by reacting substituted 1,1-dibromo-1-en-3-ynes with telluride salts (Na
1487:
Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo; Grandolini, Giuliano (1974). "A comparative study of the aromatic character of furan, thiophen, selenophen, and tellurophen".
898:
based on computational calculations, the observed blue shift suggested that upon formation of telluroxide, a different reaction pathway prevented the formation of the tellurone (PT-O
1489:
1419:
2457:
Yokozawa, Tsutomu; Yokoyama, Akihiro (2009-11-11). "Chain-Growth
Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and π-Conjugated Polymers".
948:
It had been reported by
Nakayama et al. that addition of 4 equiv of mCPBA to a tetraphenylselenophene solution also resulted in the formation of ene-dione compounds and SeO
941:
was then irradiated with 365 nm light, and it was observed that after 1 hour, complete conversion from PT to (Z)-ED had occurred with the concomitant formation of TeO
1226:
855:. The telluroketone was also found to be generated upon irradiation of a solution of the tellurophene in water with blue LED light, showing that it could be oxidized by
750:, and it shows that the LUMO is delocalized over the entire molecule, in agreement with the orbital pictures reported by Seferos et al. Using DFT calculations using the
1774:
Hay, P. Jeffrey; Wadt, Willard R. (January 1985). "Ab initio effective core potentials for molecular calculations. Potentials for the transition metal atoms Sc to Hg".
1126:, six-membered Te-B heterocycle, as observed using X-ray diffraction spectroscopy. It was found that the coordination geometries around tellurium and boron were pseudo-
1024:(a). LUMO and (b). HOMO of p-anisyl and p-cyanophenyl substituted 2,5-diaryltellurophene calculated with the B3LYP functional and 6-31G(d) basis set using Avogadro and
893:(a). LUMO+2, (b). LUMO+1, (c). LUMO, (d). HOMO, (e). HOMO-1 of telluroxide (PT-O) calculated with the B3LYP functional and 6-31G(d) basis set using Avogadro and GAMESS.
404:), and by not using a vacuum to remove the methanol as it leads to loss of the product. This improved procedure allowed the tellurophene to be isolated in 47% yield.
2505:"Influence of the heteroatom on the optoelectronic properties and transistor performance of soluble thiophene-, selenophene- and tellurophene–vinylene copolymers"
2809:
Luo, Jie; Wang, Jia-Wei; Zhang, Ji-Hong; Lai, Shan; Zhong, Di-Chang (2018). "Hydrogen-bonded organic frameworks: design, structures and potential applications".
2503:
Al-Hashimi, Mohammed; Han, Yang; Smith, Jeremy; Bazzi, Hassan S.; Alqaradawi, Siham Yousuf A.; Watkins, Scott E.; Anthopoulos, Thomas D.; Heeney, Martin (2016).
746:
could perform photoreductive defluorination. The HOMO and LUMO orbitals of 2,5-diphenyltellurophene were calculated through DFT using the computational program
563:(and therefore, higher polarity) than water, but also was found to be able to dissolve enynes better compared to water. Using a solvent combination of DMF and
2414:
Parke, Sarah M.; Boone, Michael P.; Rivard, Eric (2016). "Marriage of heavy main group elements with π-conjugated materials for optoelectronic applications".
244:
686:(a). LUMO+1, (b). LUMO, (c). HOMO, and (d). HOMO-1 of 2,5-diaryltellurophene calculated with the B3LYP functional and 6-31G(d) basis set using Avogadro and
851:
and tellurophene. It was also found that the product with absorption peak at 435 nm was a dihydroxytellurophene, and the product at 280 nm was a
344:
The first preparation of a tellurophene, tetraphenyltellurophene, was reported in 1961 by Braye et al. by reacting 1,4-dilithiotetraphenylbutadiene with
2668:
Tsao, Fu An; Cao, Levy; Grimme, Stefan; Stephan, Douglas W. (2015-10-12). "Double FLP-Alkyne
Exchange Reactions: A Facile Route to Te/B Heterocycles".
1680:
1271:
1009:) groups on the tellurophene simultaneously, this resulted in a sharp reduction of the HOMO-LUMO gap. Furthermore, the authors observed significant
451:
A variety of protocols for the synthesis of tellurophenes have been developed, such as metal-catalyzed cross coupling reactions and cyclization of
2161:
Nakayama, Juzo; Matsui, Tomoki; Sato, Noriko (June 1995). "Oxidation of
Tetraarylselenophenes and Benzoselenophene with m-Chloroperbenzoic Acid".
903:
2074:
McCormick, Theresa M.; Carrera, Elisa I.; Schon, Tyler B.; Seferos, Dwight S. (2013). "Reversible oxidation of a water-soluble tellurophene".
1250:
721:
were found to be 0.19% and 0.18%, respectively. Through DFT calculations, it was found that the main transition upon photoexcitation was a
1519:
Stein, André L.; Alves, Diego; da Rocha, Juliana T.; Nogueira, Cristina W.; Zeni, Gilson (2008). "Copper Iodide-Catalyzed
Cyclization of (
2606:
Welch, Gregory C.; Juan, Ronan R. San; Masuda, Jason D.; Stephan, Douglas W. (2006-11-17). "Reversible, Metal-Free Hydrogen Activation".
1300:
1629:
Karapala, Vamsi Krishna; Shih, Hong-Pin; Han, Chien-Chung (2018). "Cascade and Effective Syntheses of Functionalized Tellurophenes".
1956:
1373:
1178:
219:
2759:"Permanently porous hydrogen-bonded frameworks of rod-like thiophenes, selenophenes, and tellurophenes capped with MIDA boronates"
1044:
823:
position of the phenyl groups on 2,5-diphenyltellurophene. This was done by first synthesizing iodo-OEG, which was then added to
1043:
In 2016, Seferos et al. reported the synthesis of well-defined, high-molecular-weight poly-3-alkyltellurophenes (P3ATe) through
879:
In 2017, Seferos et al. reported the oxidative ring opening of 2,5-diphenyltellurophene (PT) under aerobic conditions, and with
2855:
1078:
831:, and the resulting butadiyne was treated with sodium telluride, producing the desired product. Treating the tellurophene with
2283:
Rivard, Eric (2015-06-05). "Tellurophenes and Their Emergence as Building Blocks for Polymeric and Light-emitting Materials".
577:
1298:
Rhoden, Cristiano R. B.; Zeni, Gilson (2011). "New development of synthesis and reactivity of seleno- and tellurophenes".
880:
816:
533:) under mild conditions. The telluride salts were synthesized through an earlier protocol, wherein Te/Se was reduced with
1444:
551:
such as water were thought to polarize the Te–H bond, thus increasing the negative charge on Te and making it more
313:
2850:
1357:
2563:
Tsao, Fu An; Stephan, Douglas W. (2015). "1,1-Carboboration to tellurium–boron intramolecular frustrated Lewis pairs".
1154:
close to that of C-C double bonds, indicating delocalization within the molecule. The reaction was proceeded with high
1442:
Lukevics, E.; Arsenyan, P.; Belyakov, S.; Pudova, O. (2002). "Molecular Structure of Selenophenes and Tellurophenes".
1822:
Hanwell, Marcus D; Curtis, Donald E; Lonie, David C; Vandermeersch, Tim; Zurek, Eva; Hutchison, Geoffrey R (2012).
1234:
1190:
910:) and a colorless solid which was found to be (Z)-1,4-diphenylbut-2-ene1,4-dione, (Z)-ED, through a combination of
792:
428:, an observation attributed to the larger size of the tellurium atom. These findings are also consistent with the
670:
627:
substituents were synthesized. Through monitoring the change in the optical absorption spectrum upon addition of
547:
It was found through mechanistic studies that the reaction was highly influenced by the polarity of the solvent.
694:
2122:"Ring Opening of π-Delocalized 2,5-Diphenyltellurophene by Chemical or Self-Sensitized Aerobic Photooxidation"
1162:-1,4-telluraborine, which was found to be a useful hydroboration reagent for alkenes, ketones, and aldehydes.
1097:
In 2015, Stephan et al. reported a vinyl telluroether with a pendant borane which acted as an intramolecular
1581:
926:
345:
914:
and H NMR data. This result confirmed that the tellurone is not formed even after addition of excess mCPBA.
416:
1391:
1197:
adsorption at 0 °C. Furthermore, it was found that DPT-MIDA and DPSe-MIDA adsorbed 1 mol of CO
1098:
674:
stabilizing influence, and operated through purely chalcogen bonding, unlike the monodentate receptor.
455:. Some examples are shown below. In 2008, Zeni et al. reported on the copper-catalyzed cyclizations of
116:
751:
2615:
2378:
1783:
1733:
828:
651:
640:
495:
460:
456:
433:
64:
710:
560:
483:
82:
400:
from the reaction vessel, using pure butadiyne (to decrease unwanted oxidation and polymerization
2647:
1914:
1469:
1186:
628:
608:
564:
534:
397:
128:
1145:
815:
In 2013, Seferos et al. reported the first example of a water-soluble tellurophene by attaching
612:
960:
501:
371:
2826:
2788:
2780:
2736:
2728:
2693:
2685:
2639:
2631:
2588:
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2542:
2524:
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2439:
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2339:
2300:
2265:
2257:
2221:
2213:
2178:
2143:
2099:
2091:
2051:
2043:
1997:
1989:
1952:
1906:
1863:
1845:
1799:
1751:
1697:
1656:
1648:
1608:
1600:
1550:
1542:
1461:
1369:
1349:
1325:
1317:
1246:
921:
Two different pathways for the photooxidation of 2,5-diaryltellurophene using oxygen and mCPBA
911:
832:
796:
556:
518:
420:
365:
349:
407:
2818:
2770:
2720:
2711:
Tsao, Fu An; Stephan, Douglas W. (2018). "Synthesis and reactions of 4H-1,4-telluraborine".
2677:
2623:
2572:
2532:
2516:
2466:
2423:
2386:
2331:
2292:
2249:
2205:
2170:
2133:
2083:
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1981:
1944:
1898:
1853:
1835:
1791:
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1640:
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1534:
1498:
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1424:
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1309:
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1155:
1127:
1053:
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571:
380:
267:
168:
2757:
Li, Peng-Fei; Qian, Chenxi; Lough, Alan J.; Ozin, Geoffrey A.; Seferos, Dwight S. (2016).
2367:"What Limits the Molecular Weight and Controlled Synthesis of Poly(3-alkyltellurophene)s?"
1631:
1525:
1182:
1020:
1010:
636:
526:
510:
method was hindered by low yields and the use of expensive starting materials such as the
487:
468:
379:
In 1966, Mack report a synthesis of an unsubstituted tellurophene through the reaction of
357:
180:
1417:
Fringuelli, Francesco; Taticchi, Aldo (1972). "Tellurophen and some of its derivatives".
1052:
and high molecular weights were obtained. This improvement was attributed to the lack of
92:
2619:
2382:
1939:
Gordon, Mark S.; Schmidt, Michael W. (2005), "Advances in electronic structure theory",
1787:
1737:
1269:
Braye, E. H.; Hübel, W.; Caplier, I. (1961). "New Unsaturated Heterocyclic Systems. I".
889:
148:
2537:
2504:
1948:
1858:
1823:
1014:
856:
307:
2022:"Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes"
1824:"Avogadro: an advanced semantic chemical editor, visualization, and analysis platform"
1365:
36:
2844:
982:
974:
852:
548:
511:
401:
2651:
1473:
1389:
Mack, W. (1966). "Synthesis of Tellurophene and its 2,5-Disubstituted Derivatives".
1031:
The same molecule was subjected to DFT calculations using the computational program
682:
1918:
1575:
Garrett, Graham E.; Carrera, Elisa I.; Seferos, Dwight S.; Taylor, Mark S. (2016).
1206:
871:
824:
709:
the halogenated species to drive the photoreductive elimination (PE). However, the
552:
474:
464:
393:
205:
45:
2138:
2121:
1059:
2391:
2366:
2365:
Ye, Shuyang; Steube, Marvin; Carrera, Elisa I.; Seferos, Dwight S. (2016-02-12).
1231:
Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
1644:
1170:
1025:
860:
730:
706:
687:
429:
425:
384:
333:
996:
A 2,5-diaryltellurophene with electron-donating and electron-withdrawing groups
537:
in ethanol. The synthesis of the 3-functionalized tellurophenes is as follows:
1457:
1123:
620:
616:
491:
329:
292:
159:
2830:
2784:
2732:
2689:
2635:
2584:
2528:
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2435:
2400:
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2261:
2217:
2182:
2147:
2095:
2047:
1993:
1910:
1849:
1803:
1755:
1652:
1604:
1546:
1465:
1321:
2627:
2335:
604:
441:
2792:
2740:
2697:
2643:
2592:
2546:
2486:
2443:
2351:
2269:
2253:
2225:
2209:
2103:
2055:
2001:
1867:
1840:
1701:
1660:
1612:
1554:
1403:
1329:
611:
bistellurophene receptor in which the tellurophenes were linked through an
1902:
1242:
1089:
741:
Photoreductive elimination of halogens using 2,5-diphenyltellurophene (PT)
23:
2681:
2196:
Jahnke, Ashlee A.; Seferos, Dwight S. (2011-04-29). "Polytellurophenes".
1502:
1428:
639:(THF), it was found that 2,5-bistellurophene was able to bind Cl with an
570:, the authors were able to synthesize 2,4-disubstituted tellurophenes at
388:
2174:
1284:
1201:
per mol of building block, whereas DPTe-MIDA adsorbed 0.5 mol of CO
2822:
2775:
2758:
2724:
2576:
2520:
2427:
2087:
2038:
2021:
1595:
1576:
1313:
1114:
1006:
1002:
807:
755:
437:
361:
353:
192:
2470:
2296:
1985:
1693:
1538:
576:
539:
500:
473:
406:
370:
1795:
1746:
1722:"Density-functional thermochemistry. III. The role of exact exchange"
1721:
1139:
1032:
933:
formation since 9,10-diphenylanthracene undergoes 1,4-addition with O
747:
992:
917:
729:+2 transition at 535 nm, with the LUMO+2 state possessing Te-X
595:
432:
of selenophene being greater than that of tellurophene; amongst its
306:
Except where otherwise noted, data are given for materials in their
1348:
Fringuelli, Francesco; Marino, Gianlorenzo; Taticchi, Aldo (1977).
737:
540:
436:, the order of decreasing aromaticity has been demonstrated to be:
1169:
1019:
888:
681:
624:
594:
452:
445:
415:
The geometry of tellurophene was first determined in 1973 through
139:
115:
105:
1101:(FLP). This was achieved by reacting tellurium acetylide with B(C
726:
722:
1073:
795:), since fluorine exhibits a high reactivity in water to form
1205:. Furthermore, it was observed that DPTe-MIDA exhibited weak
2498:
2496:
662: = 2290 L mol. The significantly higher
555:. To obtain a wider scope of the reaction, the authors used
44:
35:
1209:
compared to DPT-MIDA, which had a quantum yield of 6.6%.
827:
to form iodo-4-OEG-benzene. This was then subjected to a
615:
bridge. As the tellurophene was thought to function as a
964:
Phosphorescent pinacolboronate-substituted tellurophenes
1577:"Anion recognition by a bidentate chalcogen bond donor"
482:
In 2016, Taylor et al. reported a synthetic route to a
356:
metal. The tellurophene, upon recrystallization from a
1490:
Journal of the Chemical Society, Perkin Transactions 2
1420:
Journal of the Chemical Society, Perkin Transactions 1
693:
In 2013, Seferos et al. reported the first example of
559:(DMF) as the solvent since DMF not only has a higher
498:
to generate a receptor for anions such as Cl and Br.
2120:
Carrera, Elisa I.; Seferos, Dwight S. (2017-05-10).
1122:-1,2-addition across the alkyne bond, generating a
623:), 2,5-diaryltellurophenes with electron-deficient
1941:Theory and Applications of Computational Chemistry
937:to form the endoperoxide. A solution of PT in CDCl
1227:International Union of Pure and Applied Chemistry
1174:Chalcogen heterocycles capped with MIDA boronates
811:Treatment of tellurophene with hydrogen peroxide
599:Ethynylene-linked bistellurophene anion receptor
581:Synthesis of 2,4-difunctionalized tellurophenes.
204:
91:
2020:Carrera, Elisa I.; Seferos, Dwight S. (2015).
1142:to afford a five-membered Te-B-I heterocycle.
490:. This compound was then subjected to further
1093:Synthesis of telluroether with pendant borane
783:= 433 nm). Upon irradiation of the PT-Br
348:, with the former synthesized by reaction of
8:
1354:Advances in Heterocyclic Chemistry Volume 21
1343:
1341:
1339:
463:which could be further functionalized using
1017:properties of π-conjugated tellurophenes.
167:
15:
2774:
2536:
2390:
2137:
2037:
1857:
1839:
1745:
1594:
1166:Hydrogen-bonded Organic Frameworks (HOFs)
1149:Synthesis of tellurium-boron heterocycles
875:Synthesis of a water-soluble tellurophene
859:. Further, by treating a solution of the
2670:Journal of the American Chemical Society
1681:Journal of the American Chemical Society
1272:Journal of the American Chemical Society
1144:
1088:
1063:Synthesis of P3TeV using Stille coupling
1058:
991:
959:
916:
870:
806:
759:moved towards the heavier halogens (PT-F
736:
444:> selenophene > tellurophene >
392:improved upon this synthesis by using a
2242:Angewandte Chemie International Edition
1264:
1262:
1218:
1045:catalyst transfer polymerization (CTP).
419:, and has been further refined through
249:
224:
2804:
2802:
2752:
2750:
2663:
2661:
2558:
2556:
2316:
2314:
2115:
2113:
2069:
2067:
2065:
981:) was found to be degenerate with the
2015:
2013:
2011:
1934:
1932:
1930:
1928:
1883:
1881:
1879:
1877:
1817:
1815:
1813:
1769:
1767:
1765:
1715:
1713:
1711:
1672:
1670:
1624:
1622:
1570:
1568:
1566:
1564:
231:Key: TULWUZJYDBGXMY-UHFFFAOYSA-N
147:
7:
1514:
1512:
1350:"Tellurophene and Related Compounds"
1301:Organic & Biomolecular Chemistry
817:octaethylene glycol monomethyl ether
2198:Macromolecular Rapid Communications
1445:Chemistry of Heterocyclic Compounds
619:in its interaction with the anion (
603:In 2016, Taylor et al. developed a
195:
1891:Journal of Computational Chemistry
1360:. Vol. 21. pp. 119–173.
1358:Advances in Heterocyclic Chemistry
1179:Hydrogen-bonded organic frameworks
669:was found to be in agreement with
517:In 2018, Han et al. reported on a
228:InChI=1S/C4H4Te/c1-2-4-5-3-1/h1-4H
14:
1005:) and electron-withdrawing (e.g.
486:substituted tellurophene through
285:
2324:The Journal of Organic Chemistry
1949:10.1016/b978-044451719-7/50084-6
1943:, Elsevier, pp. 1167–1189,
1079:organic field effect transistors
925:By using a singlet oxygen trap,
902:). By analyzing the reaction by
279:
22:
1776:The Journal of Chemical Physics
1726:The Journal of Chemical Physics
1085:Frustrated Lewis Pair chemistry
310:(at 25 °C , 100 kPa).
1235:The Royal Society of Chemistry
328:are the tellurium analogue of
273:
1:
2139:10.1021/acs.organomet.7b00240
1720:Becke, Axel D. (April 1993).
1366:10.1016/S0065-2725(08)60731-X
2392:10.1021/acs.macromol.5b02770
1645:10.1021/acs.orglett.8b00279
398:exclude oxygen and moisture
31:
2872:
1828:Journal of Cheminformatics
1191:Thermogravimetric analysis
819:(OEG) substituents on the
793:2,3-dimethyl-1,3-butadiene
695:photoreductive elimination
956:Optoelectronic properties
884:-chloroperoxybenzoic acid
671:density functional theory
304:
260:
240:
215:
75:
63:
58:
30:
21:
1187:powder X-ray diffraction
678:Halogen photoelimination
467:via palladium-catalyzed
459:to obtain 3-substituted
2713:Chemical Communications
2628:10.1126/science.1134230
2416:Chemical Communications
2336:10.1021/acs.joc.7b02906
2076:Chemical Communications
1582:Chemical Communications
1458:10.1023/a:1020607300418
927:9,10-diphenylanthracene
863:to a -0.5 V potential (
346:tellurium tetrachloride
2856:Tellurium heterocycles
2254:10.1002/anie.201307373
2210:10.1002/marc.201100151
1841:10.1186/1758-2946-4-17
1404:10.1002/anie.196608961
1175:
1150:
1094:
1064:
1028:
997:
965:
922:
894:
876:
812:
742:
690:
600:
582:
544:
506:
479:
417:microwave spectroscopy
412:
376:
49:
40:
1903:10.1002/jcc.540141112
1523:)-Chalcogenoenynes".
1392:Angew. Chem. Int. Ed.
1243:10.1039/9781849733069
1173:
1148:
1099:frustrated Lewis pair
1092:
1062:
1023:
995:
983:singlet excited state
963:
920:
892:
874:
810:
740:
685:
598:
580:
543:
504:
496:Sonogashira couplings
477:
410:
374:
48:
39:
2682:10.1021/jacs.5b09526
1503:10.1039/P29740000332
1429:10.1039/P19720000199
829:Sonogashira coupling
775:= 416 nm, PT-Br
767:= 395 nm, PT-Cl
652:Sonogashira coupling
641:association constant
65:Preferred IUPAC name
2851:Five-membered rings
2763:Dalton Transactions
2676:(41): 13264–13267.
2620:2006Sci...314.1124W
2614:(5802): 1124–1126.
2565:Dalton Transactions
2383:2016MaMol..49.1704Y
2175:10.1246/cl.1995.485
2026:Dalton Transactions
1980:(23): 13779–13790.
1974:Inorganic Chemistry
1788:1985JChPh..82..270H
1738:1993JChPh..98.5648B
1285:10.1021/ja01482a026
561:dielectric constant
505:Taylor Tellurophene
375:Capliertellurophene
300: g·mol
129:Beilstein Reference
18:
2823:10.1039/c8ce00655e
2776:10.1039/c5dt04960a
2725:10.1039/c7cc08765a
2577:10.1039/c4dt03241a
2521:10.1039/c5sc03501e
2428:10.1039/c6cc04023c
2088:10.1039/c3cc47338d
2039:10.1039/c4dt01751j
1596:10.1039/c6cc04818h
1314:10.1039/c0ob00557f
1176:
1151:
1128:trigonal pyramidal
1095:
1065:
1029:
998:
966:
923:
904:H NMR spectroscopy
895:
877:
813:
743:
691:
609:electron-deficient
601:
583:
545:
535:sodium borohydride
507:
480:
413:
377:
314:Infobox references
50:
41:
16:
2817:(39): 5884–5898.
2769:(24): 9754–9757.
2471:10.1021/cr900041c
2465:(11): 5595–5619.
2422:(61): 9485–9505.
2297:10.1246/cl.150119
2285:Chemistry Letters
2248:(18): 4587–4591.
2163:Chemistry Letters
2132:(14): 2612–2621.
1986:10.1021/ic402485d
1897:(11): 1347–1363.
1694:10.1021/ja309404j
1589:(64): 9881–9884.
1539:10.1021/ol802060f
1533:(21): 4983–4986.
1279:(21): 4406–4413.
1252:978-0-85404-182-4
912:mass spectrometry
833:hydrogen peroxide
797:hydrofluoric acid
557:dimethylformamide
519:one-pot procedure
421:X-ray diffraction
411:improvedsynthesis
366:lithium telluride
350:diphenylacetylene
322:Chemical compound
320:
319:
117:Interactive image
54:
53:
2863:
2835:
2834:
2806:
2797:
2796:
2778:
2754:
2745:
2744:
2708:
2702:
2701:
2665:
2656:
2655:
2603:
2597:
2596:
2560:
2551:
2550:
2540:
2515:(2): 1093–1099.
2509:Chemical Science
2500:
2491:
2490:
2459:Chemical Reviews
2454:
2448:
2447:
2411:
2405:
2404:
2394:
2377:(5): 1704–1711.
2362:
2356:
2355:
2330:(4): 1969–1975.
2318:
2309:
2308:
2280:
2274:
2273:
2236:
2230:
2229:
2193:
2187:
2186:
2158:
2152:
2151:
2141:
2117:
2108:
2107:
2071:
2060:
2059:
2041:
2032:(5): 2092–2096.
2017:
2006:
2005:
1968:
1962:
1961:
1936:
1923:
1922:
1885:
1872:
1871:
1861:
1843:
1819:
1808:
1807:
1796:10.1063/1.448799
1771:
1760:
1759:
1749:
1747:10.1063/1.464913
1732:(7): 5648–5652.
1717:
1706:
1705:
1674:
1665:
1664:
1639:(6): 1550–1554.
1626:
1617:
1616:
1598:
1572:
1559:
1558:
1516:
1507:
1506:
1484:
1478:
1477:
1439:
1433:
1432:
1414:
1408:
1407:
1386:
1380:
1379:
1345:
1334:
1333:
1308:(5): 1301–1313.
1295:
1289:
1288:
1266:
1257:
1256:
1223:
1156:regioselectivity
1054:steric hindrance
1050:polydispersities
752:B3LYP functional
572:room temperature
461:chalcogenophenes
457:chalcogenoenynes
381:sodium telluride
299:
287:
281:
275:
268:Chemical formula
208:
197:
181:Gmelin Reference
171:
151:
119:
95:
32:
26:
19:
2871:
2870:
2866:
2865:
2864:
2862:
2861:
2860:
2841:
2840:
2839:
2838:
2808:
2807:
2800:
2756:
2755:
2748:
2710:
2709:
2705:
2667:
2666:
2659:
2605:
2604:
2600:
2562:
2561:
2554:
2502:
2501:
2494:
2456:
2455:
2451:
2413:
2412:
2408:
2364:
2363:
2359:
2320:
2319:
2312:
2282:
2281:
2277:
2238:
2237:
2233:
2204:(13): 943–951.
2195:
2194:
2190:
2160:
2159:
2155:
2126:Organometallics
2119:
2118:
2111:
2082:(95): 11182–4.
2073:
2072:
2063:
2019:
2018:
2009:
1970:
1969:
1965:
1959:
1938:
1937:
1926:
1887:
1886:
1875:
1821:
1820:
1811:
1773:
1772:
1763:
1719:
1718:
1709:
1676:
1675:
1668:
1632:Organic Letters
1628:
1627:
1620:
1574:
1573:
1562:
1526:Organic Letters
1518:
1517:
1510:
1486:
1485:
1481:
1441:
1440:
1436:
1416:
1415:
1411:
1388:
1387:
1383:
1376:
1347:
1346:
1337:
1297:
1296:
1292:
1268:
1267:
1260:
1253:
1237:. p. 883.
1225:
1224:
1220:
1215:
1204:
1200:
1196:
1183:Stille coupling
1168:
1137:
1133:
1112:
1108:
1104:
1087:
1071:
1041:
1011:solvatochromism
988:
980:
972:
958:
951:
944:
940:
936:
932:
909:
901:
850:
846:
842:
838:
805:
790:
786:
782:
778:
774:
770:
766:
762:
720:
716:
704:
700:
680:
668:
661:
649:
637:tetrahydrofuran
632:
593:
588:
530:
524:
494:and sequential
488:Stille coupling
469:Suzuki coupling
358:dichloromethane
342:
323:
316:
311:
297:
284:
278:
270:
256:
253:
248:
247:
236:
233:
232:
229:
223:
222:
211:
198:
183:
174:
154:
131:
122:
109:
98:
85:
71:
70:
12:
11:
5:
2869:
2867:
2859:
2858:
2853:
2843:
2842:
2837:
2836:
2798:
2746:
2719:(2): 208–211.
2703:
2657:
2598:
2552:
2492:
2449:
2406:
2371:Macromolecules
2357:
2310:
2291:(6): 730–736.
2275:
2231:
2188:
2169:(6): 485–486.
2153:
2109:
2061:
2007:
1963:
1957:
1924:
1873:
1809:
1782:(1): 270–283.
1761:
1707:
1688:(3): 951–954.
1666:
1618:
1560:
1508:
1497:(4): 332–337.
1479:
1452:(7): 763–777.
1434:
1409:
1381:
1374:
1335:
1290:
1258:
1251:
1217:
1216:
1214:
1211:
1202:
1198:
1194:
1167:
1164:
1135:
1131:
1110:
1106:
1102:
1086:
1083:
1069:
1040:
1037:
1015:optoelectronic
986:
978:
970:
957:
954:
949:
942:
938:
934:
930:
907:
899:
857:singlet oxygen
848:
844:
840:
836:
804:
803:Photooxidation
801:
788:
784:
780:
776:
772:
768:
764:
760:
718:
714:
711:quantum yields
702:
698:
679:
676:
666:
659:
647:
630:
592:
591:Anion receptor
589:
587:
584:
549:Polar solvents
528:
522:
402:side reactions
368:in 82% yield.
341:
338:
321:
318:
317:
312:
308:standard state
305:
302:
301:
295:
289:
288:
282:
276:
271:
266:
263:
262:
258:
257:
255:
254:
251:
243:
242:
241:
238:
237:
235:
234:
230:
227:
226:
218:
217:
216:
213:
212:
210:
209:
201:
199:
191:
188:
187:
184:
179:
176:
175:
173:
172:
164:
162:
156:
155:
153:
152:
144:
142:
136:
135:
132:
127:
124:
123:
121:
120:
112:
110:
103:
100:
99:
97:
96:
88:
86:
81:
78:
77:
73:
72:
68:
67:
61:
60:
56:
55:
52:
51:
42:
28:
27:
13:
10:
9:
6:
4:
3:
2:
2868:
2857:
2854:
2852:
2849:
2848:
2846:
2832:
2828:
2824:
2820:
2816:
2812:
2805:
2803:
2799:
2794:
2790:
2786:
2782:
2777:
2772:
2768:
2764:
2760:
2753:
2751:
2747:
2742:
2738:
2734:
2730:
2726:
2722:
2718:
2714:
2707:
2704:
2699:
2695:
2691:
2687:
2683:
2679:
2675:
2671:
2664:
2662:
2658:
2653:
2649:
2645:
2641:
2637:
2633:
2629:
2625:
2621:
2617:
2613:
2609:
2602:
2599:
2594:
2590:
2586:
2582:
2578:
2574:
2570:
2566:
2559:
2557:
2553:
2548:
2544:
2539:
2534:
2530:
2526:
2522:
2518:
2514:
2510:
2506:
2499:
2497:
2493:
2488:
2484:
2480:
2476:
2472:
2468:
2464:
2460:
2453:
2450:
2445:
2441:
2437:
2433:
2429:
2425:
2421:
2417:
2410:
2407:
2402:
2398:
2393:
2388:
2384:
2380:
2376:
2372:
2368:
2361:
2358:
2353:
2349:
2345:
2341:
2337:
2333:
2329:
2325:
2317:
2315:
2311:
2306:
2302:
2298:
2294:
2290:
2286:
2279:
2276:
2271:
2267:
2263:
2259:
2255:
2251:
2247:
2243:
2235:
2232:
2227:
2223:
2219:
2215:
2211:
2207:
2203:
2199:
2192:
2189:
2184:
2180:
2176:
2172:
2168:
2164:
2157:
2154:
2149:
2145:
2140:
2135:
2131:
2127:
2123:
2116:
2114:
2110:
2105:
2101:
2097:
2093:
2089:
2085:
2081:
2077:
2070:
2068:
2066:
2062:
2057:
2053:
2049:
2045:
2040:
2035:
2031:
2027:
2023:
2016:
2014:
2012:
2008:
2003:
1999:
1995:
1991:
1987:
1983:
1979:
1975:
1967:
1964:
1960:
1958:9780444517197
1954:
1950:
1946:
1942:
1935:
1933:
1931:
1929:
1925:
1920:
1916:
1912:
1908:
1904:
1900:
1896:
1892:
1884:
1882:
1880:
1878:
1874:
1869:
1865:
1860:
1855:
1851:
1847:
1842:
1837:
1833:
1829:
1825:
1818:
1816:
1814:
1810:
1805:
1801:
1797:
1793:
1789:
1785:
1781:
1777:
1770:
1768:
1766:
1762:
1757:
1753:
1748:
1743:
1739:
1735:
1731:
1727:
1723:
1716:
1714:
1712:
1708:
1703:
1699:
1695:
1691:
1687:
1683:
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1673:
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1662:
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1654:
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1597:
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1571:
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1548:
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1536:
1532:
1528:
1527:
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1515:
1513:
1509:
1504:
1500:
1496:
1492:
1491:
1483:
1480:
1475:
1471:
1467:
1463:
1459:
1455:
1451:
1447:
1446:
1438:
1435:
1430:
1426:
1422:
1421:
1413:
1410:
1405:
1401:
1397:
1394:
1393:
1385:
1382:
1377:
1375:9780120206216
1371:
1367:
1363:
1359:
1355:
1351:
1344:
1342:
1340:
1336:
1331:
1327:
1323:
1319:
1315:
1311:
1307:
1303:
1302:
1294:
1291:
1286:
1282:
1278:
1274:
1273:
1265:
1263:
1259:
1254:
1248:
1244:
1240:
1236:
1232:
1228:
1222:
1219:
1212:
1210:
1208:
1192:
1188:
1184:
1180:
1172:
1165:
1163:
1161:
1157:
1147:
1143:
1141:
1129:
1125:
1121:
1116:
1100:
1091:
1084:
1082:
1080:
1075:
1061:
1057:
1055:
1051:
1046:
1038:
1036:
1034:
1027:
1022:
1018:
1016:
1012:
1008:
1004:
994:
990:
984:
976:
975:triplet state
962:
955:
953:
946:
928:
919:
915:
913:
905:
891:
887:
885:
883:
873:
869:
866:
862:
858:
854:
853:telluroketone
834:
830:
826:
822:
818:
809:
802:
800:
798:
794:
757:
753:
749:
739:
735:
732:
728:
724:
712:
708:
696:
689:
684:
677:
675:
672:
665:
658:
653:
646:
642:
638:
634:
626:
622:
618:
614:
610:
606:
597:
590:
585:
579:
575:
573:
569:
567:
562:
558:
554:
550:
542:
538:
536:
532:
520:
515:
513:
512:Weinreb amide
503:
499:
497:
493:
489:
485:
484:perfluoroaryl
476:
472:
470:
466:
465:boronic acids
462:
458:
454:
449:
447:
443:
439:
435:
431:
427:
422:
418:
409:
405:
403:
399:
395:
390:
386:
382:
373:
369:
367:
363:
359:
355:
351:
347:
339:
337:
335:
331:
327:
326:Tellurophenes
315:
309:
303:
296:
294:
291:
290:
272:
269:
265:
264:
259:
250:
246:
239:
225:
221:
214:
207:
203:
202:
200:
194:
190:
189:
185:
182:
178:
177:
170:
166:
165:
163:
161:
158:
157:
150:
146:
145:
143:
141:
138:
137:
133:
130:
126:
125:
118:
114:
113:
111:
107:
102:
101:
94:
90:
89:
87:
84:
80:
79:
74:
66:
62:
57:
47:
43:
38:
34:
33:
29:
25:
20:
17:Tellurophene
2814:
2811:CrystEngComm
2810:
2766:
2762:
2716:
2712:
2706:
2673:
2669:
2611:
2607:
2601:
2571:(1): 71–74.
2568:
2564:
2512:
2508:
2462:
2458:
2452:
2419:
2415:
2409:
2374:
2370:
2360:
2327:
2323:
2288:
2284:
2278:
2245:
2241:
2234:
2201:
2197:
2191:
2166:
2162:
2156:
2129:
2125:
2079:
2075:
2029:
2025:
1977:
1973:
1966:
1940:
1894:
1890:
1831:
1827:
1779:
1775:
1729:
1725:
1685:
1679:
1636:
1630:
1586:
1580:
1530:
1524:
1520:
1494:
1488:
1482:
1449:
1443:
1437:
1418:
1412:
1395:
1390:
1384:
1353:
1305:
1299:
1293:
1276:
1270:
1230:
1221:
1207:fluorescence
1177:
1159:
1152:
1124:zwitterionic
1119:
1096:
1066:
1042:
1030:
999:
967:
947:
924:
896:
881:
878:
864:
825:4-iodophenol
820:
814:
744:
713:for PE of Cl
692:
663:
656:
644:
602:
565:
553:nucleophilic
546:
516:
508:
481:
450:
414:
394:Schlenk line
378:
343:
334:selenophenes
325:
324:
76:Identifiers
69:Tellurophene
1423:: 199–203.
1398:(10): 896.
861:telluroxide
731:antibonding
707:photoexcite
430:aromaticity
426:selenophene
385:diacetylene
261:Properties
149:CHEBI:30858
2845:Categories
1213:References
1134:or bind CO
756:π* orbital
697:(PE) of Cl
621:Lewis base
617:Lewis acid
613:ethynylene
586:Reactivity
492:iodination
330:thiophenes
293:Molar mass
160:ChemSpider
104:3D model (
83:CAS Number
2831:1466-8033
2785:1477-9226
2733:1359-7345
2690:0002-7863
2636:0036-8075
2585:1477-9226
2529:2041-6520
2479:0009-2665
2436:1359-7345
2401:0024-9297
2344:0022-3263
2305:0366-7022
2262:1433-7851
2218:1022-1336
2183:0366-7022
2148:0276-7333
2096:1359-7345
2048:1477-9226
1994:0020-1669
1911:0192-8651
1850:1758-2946
1834:(1): 17.
1804:0021-9606
1756:0021-9606
1653:1523-7060
1605:1359-7345
1547:1523-7060
1466:0009-3122
1322:1477-0520
605:bidentate
442:thiophene
434:congeners
340:Synthesis
2793:26758802
2741:29230466
2698:26447492
2652:20333088
2644:17110572
2593:25408099
2547:29896373
2487:19757808
2444:27344980
2352:29392944
2270:24668889
2226:21538646
2104:24149322
2056:25154588
2002:24251356
1868:22889332
1702:23286232
1661:29494165
1613:27376877
1555:18826235
1474:92305752
1330:21210032
1229:(2014).
1039:Polymers
389:methanol
252:C1=CC=C1
93:288-08-4
2616:Bibcode
2608:Science
2538:5954972
2379:Bibcode
1919:3358041
1859:3542060
1784:Bibcode
1734:Bibcode
1115:pentane
1026:GAMESS.
688:GAMESS.
478:5.05Wk4
438:benzene
362:ethanol
354:lithium
193:PubChem
186:647889
134:103225
2829:
2791:
2783:
2739:
2731:
2696:
2688:
2650:
2642:
2634:
2591:
2583:
2545:
2535:
2527:
2485:
2477:
2442:
2434:
2399:
2350:
2342:
2303:
2268:
2260:
2224:
2216:
2181:
2146:
2102:
2094:
2054:
2046:
2000:
1992:
1955:
1917:
1909:
1866:
1856:
1848:
1802:
1754:
1700:
1659:
1651:
1611:
1603:
1553:
1545:
1472:
1464:
1372:
1328:
1320:
1249:
1140:iodine
1072:of 10
1033:GAMESS
748:GAMESS
717:and Br
701:and Br
635:Cl in
453:enynes
298:179.68
245:SMILES
206:136131
169:119908
59:Names
2648:S2CID
1915:S2CID
1470:S2CID
821:para-
625:arene
568:-BuOH
446:furan
440:>
383:with
220:InChI
140:ChEBI
106:JSmol
2827:ISSN
2789:PMID
2781:ISSN
2737:PMID
2729:ISSN
2694:PMID
2686:ISSN
2640:PMID
2632:ISSN
2589:PMID
2581:ISSN
2543:PMID
2525:ISSN
2483:PMID
2475:ISSN
2440:PMID
2432:ISSN
2397:ISSN
2348:PMID
2340:ISSN
2301:ISSN
2266:PMID
2258:ISSN
2222:PMID
2214:ISSN
2179:ISSN
2144:ISSN
2100:PMID
2092:ISSN
2052:PMID
2044:ISSN
1998:PMID
1990:ISSN
1953:ISBN
1907:ISSN
1864:PMID
1846:ISSN
1800:ISSN
1752:ISSN
1698:PMID
1657:PMID
1649:ISSN
1609:PMID
1601:ISSN
1551:PMID
1543:ISSN
1495:1974
1462:ISSN
1370:ISBN
1326:PMID
1318:ISSN
1247:ISBN
882:meta
727:LUMO
723:HOMO
607:and
352:and
332:and
2819:doi
2771:doi
2721:doi
2678:doi
2674:137
2624:doi
2612:314
2573:doi
2533:PMC
2517:doi
2467:doi
2463:109
2424:doi
2387:doi
2332:doi
2293:doi
2250:doi
2206:doi
2171:doi
2134:doi
2084:doi
2034:doi
1982:doi
1945:doi
1899:doi
1854:PMC
1836:doi
1792:doi
1742:doi
1690:doi
1686:135
1641:doi
1591:doi
1535:doi
1499:doi
1454:doi
1425:doi
1400:doi
1362:doi
1310:doi
1281:doi
1239:doi
1120:cis
1113:in
1074:kDa
1003:OMe
865:vs.
781:max
779:: λ
773:max
771:: λ
765:max
763:: λ
725:to
525:Te/
396:to
387:in
196:CID
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1976:.
1951:,
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527:Na
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1107:5
1105:F
1103:6
1070:n
1068:M
987:1
979:3
971:2
950:2
943:2
939:3
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931:2
908:2
900:2
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847:O
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785:2
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