582:
from the less electronegative antimony results in a more positive reduction potential than in the phosphorus ion. Sterically speaking, arsenic (V), being a larger ion than phosphorus (V), possesses a more stable, planar coordinated porphyrin as opposed to the ruffled porphyrin coordinated to phosphorus. Oppositely, a pnictogen element too large to neatly coordinate into the porphyrin hole like bismuth causes a disruption of symmetry in the ring.
544:, a commonly excited molecule in photochemistry, to octaethylporphyrin and TEP. The relatively low potentials of the porphyrins yield highly energetic charge-separated states upon the transfer of the electron from naphthalene. The axial and peripheral substituent diversity is key to accessing the wide range of charge-separated states and electron transfer across electronically diverse reactants to form a great variety of redox products.
357:
Generally, as the electronegativity of the groups increases, the oxidative and reductive potentials become more positive indicating the complexâs ability to accept an electron more easily. A 2022 study by Sharma et al. compounded the axial group electrochemical effects with the effects of outer porphyrin ring aryl substituents to determine their overall influence on P-centered porphyrin electrochemistry. More
379:
Mn complex allows the reduction of the tin(IV) ion to tin(III) through the porphyrin as an electron carrier in a similar fashion to the 2015 publication. The photoreduction applications mimic those of the natural porphyrin role in photosynthesis; however, the phosphorus (V) allows for tuning and more wide-ranging applications than transition metal ions.
186:
process for binding alcohols to phosphorus cores. In a similar synthetic process, Susumu et al. linked several modified porphyrins in a center-to-edge bonding scheme. The chlorines on a P-centered porphyrin are first substituted by an external hydroxyphenyl group on another porphyrin. The substituent porphyrins are then refluxed with POCl
537:
porphyrin electron carriers in catalysis. Photovoltaic cells involving NiO complexes supplemented with high oxidation potential p-centered porphyrins improve cell efficiency as is the case in indium tin oxide cells with porphyrins containing axial carbazolylvinylnaphthalimides bound to a core phosphorus.
581:
Phosphorus (V) is a prevalent ion center in modified porphyrin complexes but is not the only group 15 element that has been used in place of a transition metal ion. Antimony and bismuth have also been identified as suitable porphyrin cores as early as 1991 by
Barbour et al. Stronger electron donating
378:
reactions. The ability to form an effective catalytic system is a result of the high redox potential (1.62-1.65V) of the phosphorus-modified porphyrin bound to tin (II) oxide. In 2016, he devised a similar application for p-centered porphyrins with tin (IV) oxide and Mn(II)typ. Photooxidation of the
304:
conjugated system. This phenomenon, like saddling and doming, has been observed as well with small transition metal ions like nickel II. The ruffling effect of phosphorus (V) in a porphyrin is apparent because of the small size of the ion. More electronegative axial groups result in greater ruffling
198:
Synthesis of a phosphole-substituted porphyrin or phosphaporphyrin involves a more complex chemical route. Phosphaporphyrins are not created using an unmodified porphyrin ring as a synthetic reagent. As reported by Matano and
Imahori in 2008, a phosphaporphyrin is constructed with a phosphole linked
622:
to form substituted alkenes. Like porphyrins, electronic properties of this complex are also tunable through the influence of various functional groups. In 2009, these molecules were examined in comparison to porphyrins due to their more restricted Ï-systems and carefully characterized with a focus
247:
Several varieties of the P-centered porphyrin exist. The porphyrin with a core phosphorus (V) ion can be tuned with additional substituents added to either the outside of the polycyclic ring system or axially to the core phosphorus. Meso-substituted porphyrins like meso-tetra-p-tolylporphyrin (TTP)
226:
185:
like bromine have been used successfully in place of chlorine for this synthesis method of P-centered rings. More syntheses with complex alcohols have been reported. Porphyrins functionalized with axial carbazolylvinylnaphthalimides are synthesized using similar methods to the previously described
536:
P-centered porphyrins typically react in redox reactions where they serve as tunable intermediate electron carriers in biological reactions for DNA degradation as well as other industrial catalytic reactions. Tn (II/IV) oxide is photoreduced by iridium and manganese complexes through p-centered
356:
of porphyrins. Like the electronegativity effects of the axial group on P-N bonding distance and plane ruffling, electronegativity effects the molecular redox potentials. Akiba et al. in 2002 were first to quantify the redox potentials of various porphyrin molecules with different axial groups.
248:
and octaethylporphyrin (OEP) are often used in synthesis of the core phosphorus porphyrin. Substituents on the hypervalent phosphorus also result in the existence of a diverse array of molecules with varying properties. Axial substituents on the phosphorus include a wide variety of
598:
Calixphyrins are analogous to porphyrins with two of the hydrocarbon bridges between pyrroles fully saturated. Like phosphaporphyrin, a calixphyrin pyrrole can be substituted with a phosphole to form a P-centered calixphyrin. The results of increased saturation are mixed sp and sp
325:(NCIS) values used to quantify aromaticity indicate the aromatic character of the phosphaporphyrins. These values however are more positive than NICS values for the undistorted four-pyrrole structure, which is a result of the less planar Ï-system in phosphaporphyrins.
519:
via two mechanisms to degrade guanine. The first mechanism involves electron transfer that degrades a sequence of consecutive guanine nucleotides while the second mechanism proceeds via oxygen radical formation that indiscriminately destroys guanine residues in DNA.
411:(NLO) properties like molecular hyperpolarizability in metal-phosphole hybrids yield unique electrochemical applications. A variety of phosphole-metal complexes have been synthesized to bridge copper II and silver I metal ions through phosphorus-containing
406:
and unique electrochemical applications. The phosphole component has been shown by Reau et al. in 2002 to be prone to hyperpolarizability. This characteristic is more true of phospholes when bound to a palladium II ion as is often the case in porphyrins.
555:
Phosphaporphyrins after synthesis can be complexed with metals like the unmodified porphyrin molecule. Nickel, palladium, and platinum can be coordinated as the metal center of a phosphaporphyrin by reacting the conjugated ring with metal salts like
320:
as is typical of phosphorus centers. In addition to the bound phenyl group, these molecules may also possess a metal ion core that coordinates to the three pyrroles and phosphole and distorts the naturally planar molecule. Very negative
656:
complexes that engage in similar chemistry to the porphyrinoids. The 20Ï systems are synthesized from 18Ï porphyrins via redox-coupled complexation. Although the 4Ïn conjugated system would suggest that the molecule exhibits
365:
in the absorption spectra as opposed to less withdrawing groups like a simple phenyl. Additionally, the high oxidation potential of the modified porphyrins allows for their use in electrochemical applications. Artificial
229:
General route for the synthesis of a phosphaporphyrin before its coordination to a central metal ion. Meso-substituents present on a final porphyrinoid product are commonly added to the phosphole and pyrrole starting
635:
present in other porphyrinoids. A phosphole replacing a pyrrole allows for similar chemistry to other phosphaporphyrinoids with increased flexibility of the tetradentate ligand by virtue of sp hybridization.
234:
Metals can be coordinated in the core of the phosphaporphyrin by introducing metal salts. Rhodium metal is very easily inserted into the core of a phosphaporphyrin without the presence of a stabilizing
540:
Phosphorus (V) porphyrins are particularly good electron carriers in redox reactions because of their adjustable reduction potential. Poddutoori et al. in 2021 investigated the electron transfer of
551:
Energy diagram of charge transfer between the porphyrin and naphthalene in complex. Different porphyrins, meso-tetra-p-tolylporphyrin and octaethylporphyrin, possess different reduction potentials
870:âSynthesis, Structure, Electrochemistry, and Spectroelectrochemistry of Hypervalent Phosphorus(V) Octaethylporphyrins and Theoretical Analysis of the Nature of the PO Bond in P(OEP)(CH2CH3)(O)â
415:
ligands. The new electrochemically stabile complexes indicate the importance of the NLO properties that are unique to phosphaporphyrins by virtue of their phosphorus-integrated Ï-system.
300:
of the axial substituents increase. Porphyrins bound to unnaturally small ions at the core result in ruffling, a deviation in position of the carbon atoms from the median plane of the
352:
Phosphorus core porphyrins have been researched extensively to assess their photo and electrochemical properties. Axial groups bonded to the core phosphorus exert influence on the
900:âHypervalent Phosphorus(V) Porphyrins with meso-Methoxyphenyl Substituents: Significance of the Number and Position of Methoxy Groups in Promoting Intramolecular Charge Transferâ
898:
Sharma, Jatan K.; Bayard, Brandon J.; Zosel, Nick; Ali, Syeda S.; Holzer, Noah; Nesterov, Vladimir N.; Karr, Paul A.; DâSouza, Francis; and
Poddutoori, Prashanth K. (2022).
836:âPreparation of Group 15 (Phosphorus, Antimony, and Bismuth) Complexes of meso-Tetra-p-tolylporphyrin (TTP) and X-ray Crystal Structure of [Sb(TTP)(OCH(CH3)2)2]Clâ
524:
374:. Poddutoori et al. in 2015 explored the electrochemical applications of the p-core porphyrins deposited with Ir(III)Cp on tin (II) oxide to form a pre-catalyst for
423:
As early as 2002, axial substituents on the phosphorus core have been utilized for photochemistry. Reddy and Maiya pioneered the use of a p-centered porphyrin with
1313:âSimilar Mutagenicity of Photoactivated Porphyrins and Ultraviolet A Radiation in Mouse Embryonic Fibroblasts: Involvement of Oxidative DNA Lesions in Mutagenesisâ
926:
Poddutoori, Prashanth K; Bayard, Brandon J.; Holzer, Noah; Seetharaman, Sairaman; Zarrabi, Niloofar; Weidner, Nathan; Karr, Paul A; and DâSouza, Francis. (2021).
203:
which is then bound to another pyrrole molecule. Specifically, addition of 2,5-bis(hydroxymethyl)-1-phenyl-1-thiophosphole to excess pyrrole in the presence of BF
774:âInterfacial electron transfer in photoanodes based on phosphorus(v) porphyrin sensitizers co-deposited on SnO2 with the Ir(III)Cp* water oxidation precatalystâ
190:
to synthesize the final center-to-edge porphyrin array. The resulting P-centered complex consists of three porphyrins with phosphorus atoms bound at each core.
447:
of the isomerization. The high yield of both isomers after several iterations of the reaction indicates that the photoswitching is a reliable, stable process.
383:
1334:
Matano, Yoshihiro; Miyajima, Tooru; Ochi, Noriaki; Nakabuchi, Takashi; Shiro, Motoo; Nakao, Yoshihide; Sakaki, Shigeyoshi; and
Imahori, Hiroshi. (2008).
1412:âRedox-Coupled Complexation of 23-Phospha-21-thiaporphyrin with Group 10 Metals: A Convenient Access to Stable Core-Modified IsophlorinâMetal Complexesâ
1165:
Meshkov, Ivan N.; Bulach, VĂ©ronique; Gorbunova, Yulia G.; Gostev, Fedor E.; Nadtochenko, Victor A.; Tsivadze, Aslan Yu; and
Hosseini, Mir Wais. (2017).
928:âRational Design and Synthesis of OEP and TPP Centered Phosphorus(V) PorphyrinâNaphthalene Conjugates: Triplet Formation via Rapid Charge Recombinationâ
451:
586:
1290:âGuanine-specific DNA oxidation photosensitized by the tetraphenylporphyrin phosphorus(V) complex via singlet oxygen generation and electron transferâ
219:
548:
98:
527:
Excitation of a porphyrin-DNA complex and the resulting energy cascade diagram. Two pathways are shown that produce guanine nucleotide degradation
139:
to produce Cl, OH, and other similar compounds. Other researchers including
Poddutoori in 2015 and 2022 have used such synthetic methods to yield
119:
at the porphyrin core by
Barbour et al. in 1992 included syntheses of P-centered porphyrin compounds from meso-Tetra-p-tolylporphyrin (TTP).
640:
391:
67:, porphyrins are used in biological systems to perform light-energy conversion and modified synthetically to perform similar functions as a
611:
147:
665:
589:
Other pnictogen-centered porphyrins in ascending order of ion size. From left to right: arsenic, antimony, and bismuth porphyrin complexes
296:
experiments reveal that substituents affect the structure properties of these complexes. The porphyrin P-N bond distances decrease as the
101:
Two varieties of P-centered porhpyrins: phosphorus core porphyrin (left) and phosphaporphyrin coordinated to a general metal, M (right).
868:
Akiba, Kin-ya; Nadano, Ryo; Satoh, Wataru; Yamamoto, Yohsuke; Nagase, Shigeru; Ou, Zhongping; Tan, Xiaoyu; and Kadish, Karl M. (2001).
804:âPhosphorus(V) Porphyrin-Manganese(II) Terpyridine Conjugates: Synthesis, Spectroscopy, and Photo-Oxidation Studies on a SnO2 Surfaceâ
1389:âMeso-Substituent Effects on Redox Properties of the 5,10-Porphodimethene-Type P,S,N2-Hybrid Calixphyrins and Their Metal Complexesâ
1260:
Borgström, Magnus; Blart, Errol; Boschloo, Gerrit; Mukhtar, Emad; Hagfeldt, Anders; Hammarström, Leif; and Odobel, Fabrice. (2005).
503:, stopping proliferation. Tetraphenylporphyrin phosphorus (V) complexes with DNA and possesses an oxidation potential larger than
1440:
29:
309:
groups have a similar effect. The degree to which various substituents cause ruffling was determined by Akiba et al. in 2001.
454:
Reversible (E/Z) Isomerization of an axial azobenzene substituent bound to a core phosphorus ion upon irradiation by UV light
977:âSynthesis and photophysical properties of phosphorus(v) porphyrins functionalized with axial carbazolylvinylnaphthalimidesâ
523:
345:
data to those suspended in dilute solution. Axial ligand substitution of the metal was proposed as a method of varying the
1363:âPhosphorus-Containing Hybrid Calixphyrins:â Promising Mixed-Donor Ligands for Visible and Efficient Palladium Catalystsâ
1361:
Matano, Yoshihiro; Miyajima, Tooru; Nakabuchi, Takashi; Imahori, Hiroshi; Ochi, Noriaki; and Sakaki, Shigeyoshi. (2006).
1336:âSyntheses, Structures, and Coordination Chemistry of Phosphole-Containing Hybrid Calixphyrins: Promising Macrocyclic P,N
322:
131:
TTP forms the P-centered porphyrin molecule Cl. Several chemical variants were synthesized by refluxing in solutions of
668:
A conjugated 20Ï isophlorin coordinated to a general metal ion, M, and containing a substituted phenyl-bound phosphole
358:
1300:
1289:
834:
Barbour, Tanya; Belcher, Warwick J.; Brothers, Penelope J.; Rickard, Clifton E. F.; and Ware, David C. (1992).
75:
1223:
1212:
618:
Matano et al. in 2006 used the first ever P,S-hybridized calixphyrin coordinated to palladium to catalyze the
386:
Route of electron transfer through a P-centered porphyrin in the redox pathway of Mn(II)typ and tin (IV) oxide
802:
Poddutoori, Prashanth K.; Lim, Gary N.; Pilkington, Melanie; DâSouza, Francis; and van der Est, Art. (2016).
398:(CV) experiments with phosphaporphyrins reveal that the single pyrrole to phosphole substitution narrows the
496:
49:
1188:
Fave, Claire; Hissler, Muriel; Sénéchal, Katell; Ledoux, Isabelle; Zyssb, Joseph; and Réau, Régis. (2002).
1141:âEnergetics of Saddling versus Ruffling in Metalloporphyrins: Unusual Ruffled Dodecasubstituted Porphyrinsâ
382:
1410:
Matano, Yoshihiro; Nakabuchi, Takashi; Fujishige, Shinya; Nakano, Haruyuki; and
Imahori, Hiroshi. (2008).
692:
Schick, Alan; Schreiman, Irwin C.; Wagner, Richard W.; Lindsey, Jonathan S.; and Bocian, David F. (1989).
120:
1090:âPhosphole-containing calixpyrroles, calixphyrins, and porphyrins: synthesis and coordination chemistryâ
1024:
Matano, Yoshihiro; Nakabuchi, Takashi; Miyajima, Tooru; Imahori, Hiroshi; and Nakano, Haruyuki. (2006).
772:
Poddutoori, Prashanth K.; Thomsen, Julianne M.; Milot, Rebecca L.; Sheehan, Stafford W.; et al. (2015).
632:
600:
215:
614:
Phosphole-substituted calixphyrin. The phosphole bound to phenyl sits between the two saturated bridges
998:
Susumu, Kimihiro; Tanaka, Kazuyoshi; Shimidzu, Takeo; Takeuchi, Yasuko; and Segawa, Hiroshi. (1999).
1118:âSynthesis, structures, and aromaticity of phosphole-containing porphyrins and their metal complexesâ
484:
212:
91:
1177:
1166:
987:
976:
784:
773:
225:
1445:
715:
Gong, Xianchang; Milic, Tatjana; Xu, Chang; Batteas, James D.; and Drain, Charles
Michael. (2002).
450:
444:
353:
1200:
1189:
1066:
1055:
1010:
999:
750:
742:
631:
Calixpyrroles have all four hydrocarbon bridges fully saturated, breaking the conjugation between
585:
1236:âAgI Bimetallic Molecular Clips with Adaptive Coordination Behavior for Supramolecular Chemistryâ
395:
317:
222:(DDQ) oxidation of the product yields the highly conjugated 18Ï-system phosphaporphyrin product.
1000:âSynthesis and photophysical properties of âcenter-to-edgeâ type phosphorus(V) porphyrin arraysâ
1128:
1117:
1262:âSensitized Hole Injection of Phosphorus Porphyrin into NiO:â Toward New Photovoltaic Devicesâ
297:
200:
26:
337:
studies because of their highly conjugated Ï-systems. Isolated monolayers of porphyrins with
150:
General synthesis for the insertion of a phosphorus (V) ion into the core of a porphyrin ring
547:
408:
293:
116:
97:
60:
511:
interaction, a p-centered porphyrin electron is excited with 365 nm radiation to the S
370:
systems can be fine-tuned by the addition of different functional groups for catalysis and
1213:âChemistry of Bridging Phosphanes: CuI Dimers Bearing 2,5-Bis(2-pyridyl)phosphole Ligandsâ
375:
346:
211:
results in the phosphatripyrrane precursor. A phosphaporphyrinogen ring is formed through
159:
1211:
Nohra, Brigitte; Rodriguez-Sanz, Elena; Lescop Dr., Christophe; and RĂ©au, RĂ©gis. (2008).
1190:âLigandtrans-effect: using an old concept as a novel approach to bis(dipolar) NLO-phoresâ
938:
927:
910:
899:
814:
803:
623:
on the tunability of their electronic properties with different metals and substituents.
63:
like Cu II, Zn II, Co II, Fe III. Being highly conjugated molecules with many accessible
465:
have also been made more efficient by hole injection of phosphorus porphyrins, yielding
1311:
Besaratinia, Ahmad; Bates, Steven E.; Synold, Timothy W.; and
Pfeifer, Gerd P. (2004).
516:
371:
367:
306:
1434:
619:
508:
428:
403:
399:
334:
154:
Later syntheses have been performed with other phosphorus precursors, including PhPCl
83:
64:
1151:
1140:
661:
character, geometric and magnetic criteria confirm that the complex is nonaromatic.
961:
950:
846:
835:
658:
639:
466:
458:
440:
342:
53:
1399:
1388:
1387:
Matano, Yoshihiro; Fujita, Masato; Miyajima, Tooru; and Imahori, Hiroshi. (2009).
1288:
Hirakawa, F. Kazutaka; Kawanishi, Shosuke; Hirano, Toru; Segawa, Hiroshi. (2007).
743:âA molecular photoswitch based on an âaxial-bondingâ type phosphorus(v) porphyrinâ
610:
361:
on the outside of the porphyrin like 3,4,5-trimethoxyphenyl resulted in a greater
146:
44:
atom at their core or porphyrins with one of the four pyrroles substituted for a
664:
653:
604:
541:
500:
140:
68:
1056:âDesign and synthesis of phosphole-based Ï systems for novel organic materialsâ
704:
693:
1234:
Welsch, Stefan; Lescop, Christophe; Scheer, Manfred; and RĂ©au, RĂ©gis. (2008).
949:
Furuyama, Taniyuki; Maeda, Kazuya; Maeda, Hajime; and Segi, Masahito. (2019).
432:
424:
178:
41:
1422:
1411:
1373:
1362:
1350:
1335:
1323:
1312:
1272:
1261:
1246:
1235:
1167:âTuning photochemical properties of phosphorus(v) porphyrin photosensitizersâ
1100:
1089:
1036:
1025:
880:
869:
727:
716:
436:
412:
362:
236:
87:
72:
45:
37:
469:
reactants that are regenerated at a much faster rate than is typical for a
143:
phosphorus (V) bonded to porphyrin as well as axial alcohols substituents.
1340:,X-Mixed Donor Ligands for Designing Reactive Transition Metal Complexesâ
301:
182:
136:
132:
33:
504:
56:
435:
of 345 nm. The process of isomerization is made possible through
1116:
Matano, Yoshihiro; Nakabuchi, Takashi; and Imahori, Hiroshi. (2010).
975:
Zhan, Yong; Cao, Kaiyu; Wang, Chenguang; Jia, Junhui; et al. (2012).
492:
349:
properties and has since been done extensively with phosphorus ions.
338:
313:
265:
94:
to phosphorus result in other changes to the porphyrinâs chemistry.
82:
are much smaller than the typical metal centers and bestow distinct
643:
Phosphole-substituted calixpyrrole lacking a highly conjugated ring
694:âSpectroscopic characterization of porphyrin monolayer assembliesâ
663:
638:
609:
584:
546:
522:
449:
381:
249:
224:
145:
96:
951:âChemoselective Synthesis of Aryloxy-Substituted Phthalocyaninesâ
470:
316:
group resting above the porphyrin plane in a trigonal pyramidal
281:
79:
48:. Unmodified porphyrins are composed of pyrroles and linked by
507:(1.4-1.8V > 1.24V). Upon coupling to DNA fragments through
488:
462:
218:
of the phosphatripyrrane with a 2,5-difunctionalized pyrrole.
717:âPreparation and Characterization of Porphyrin Nanoparticlesâ
402:
gap in an 18 Ï-system, allowing for a more easily accessible
603:
of the ring carbons and the extension of the metal-nitrogen
86:
properties unto the porphyrin. Similar compounds with other
1294:
The Journal of Photochemistry and Photobiology B: Biology
390:
Phosphaporphyrins have been studied to a lesser degree.
312:
Phosphaporphyrins possess phospholes usually bound to a
1026:âSynthesis of a Phosphorus-Containing Hybrid Porphyrinâ
491:
in cases of extreme cell proliferation as is common in
333:
Unmodified porphyrins have been identified and used in
741:Reddya, D. Raghunath and Maiya, Bhaskar G. (2000).
90:cores (As, Sb, Bi) or different polycyclic rings
1088:Matano, Yoshihiro and Imahori, Hiroshi. (2009).
1054:Matano, Yoshihiro and Imahori, Hiroshi. (2009).
443:by the highly conjugated porphyrin ring and the
8:
1383:
1381:
1284:
1282:
1280:
1161:
1159:
1139:Conradie, Jeanet and Ghosh, Abhik. (2017).
1020:
1018:
1084:
1082:
1080:
1078:
1076:
1074:
1050:
1048:
1046:
1044:
174:yield similar porphyrin products with a PF
1256:
1254:
1112:
1110:
1108:
971:
969:
427:substituents capable of reversible (E/Z)
1416:Journal of the American Chemical Society
1367:Journal of the American Chemical Society
1344:Journal of the American Chemical Society
721:Journal of the American Chemical Society
698:Journal of the American Chemical Society
894:
892:
890:
888:
864:
862:
860:
858:
856:
854:
737:
735:
678:
32:ring systems consisting of either four
922:
920:
918:
798:
796:
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792:
768:
766:
764:
762:
760:
758:
1301:DOI: 10.1016/j.jphotobiol.2007.04.001
830:
828:
826:
824:
822:
688:
686:
684:
682:
568:in DCM/dichlorobenzene respectively.
7:
487:(PDT) is used to target and destroy
1266:The Journal of Physical Chemistry B
20:Phosphorus-centered (or P-centered)
939:DOI: 10.1021/acs.inorgchem.1c02531
911:DOI: 10.1021/acs.inorgchem.2c01648
815:DOI: 10.1021/acs.inorgchem.6b01924
572:Derivatives and structural analogs
495:. Porphyrins are used to generate
354:oxidation and reduction potentials
323:nucleus independent chemical shift
14:
292:), and halide functional groups.
955:The Journal of Organic Chemistry
341:transition metals yield similar
158:and octaethylporphyrin (OEP) in
329:Photoelectrochemical properties
1060:Organic Biomolecular Chemistry
981:Organic Biomolecular Chemistry
1:
1152:DOI: 10.1021/acsomega.7b01004
1129:DOI: 10.1351/PAC-CON-09-08-05
1094:Accounts of Chemical Research
778:Journal of Material Chemistry
1004:J. Chem. Soc., Perkin Trans.
962:DOI: 10.1021/acs.joc.9b02126
785:DOI: DOI: 10.1039/c4ta07018f
652:Isophlorins are less stable
220:Dichloro-dicyanobenzoquinone
1224:DOI: 10.1002/chem.200701423
515:state and proceeds down an
359:electron-withdrawing groups
1462:
419:Photochemical applications
577:Other pnictogen ion cores
16:Organophosphorus compound
847:DOI: 10.1021/ic00031a011
705:DOI: 10.1021/ja00186a030
52:bridges often acting as
1441:Phosphorus heterocycles
1194:Chemical Communications
1178:DOI: 10.1039/c7cc06052a
1171:Chemical Communications
988:DOI: 10.1039/c2ob26478a
747:Chemical Communications
499:in the body to degrade
480:Biological applications
115:Early experiments with
78:. Phosphorus III and V
50:unsaturated hydrocarbon
1423:DOI: 10.1021/ja807742g
1400:DOI: 10.1021/om900745t
1374:DOI: 10.1021/ja0640039
1351:DOI: 10.1021/ja076709o
1324:DOI: 10.1021/bi048717c
1273:DOI: 10.1021/jp054034a
1247:DOI: 10.1021/ic801222j
1101:DOI: 10.1021/ar900075e
1037:DOI: 10.1021/ol0622763
881:DOI: 10.1021/ic010595e
728:DOI: 10.1021/ja027405z
669:
644:
615:
590:
552:
528:
497:radical oxygen species
455:
431:upon irradiation at a
387:
239:-substituted pyrrole.
231:
151:
121:Phosphorus oxychloride
102:
1201:DOI: 10.1039/B203149C
1067:DOI: 10.1039/b819255n
1011:DOI: 10.1039/A809840I
751:DOI: 10.1039/b007784o
667:
642:
613:
588:
550:
526:
453:
385:
228:
149:
100:
485:Photodynamic therapy
1421:(49): 16446-16447.
1372:(36): 11760-11761.
1322:(49): 15557-15566.
1271:(48): 22928-22934.
1240:Inorganic Chemistry
960:(21): 14306-14312.
937:(23): 17952-17965.
932:Inorganic Chemistry
909:(42): 16573â16585.
904:Inorganic Chemistry
874:Inorganic Chemistry
840:Inorganic Chemistry
813:(21): 11383-11395.
808:Inorganic Chemistry
726:(48): 14290-14291.
36:with inward-facing
670:
645:
616:
591:
553:
529:
456:
396:cyclic voltammetry
388:
318:molecular geometry
232:
152:
103:
59:centered around a
1398:(21): 6213-6217.
1245:(19): 8592-8594.
1222:(11): 3391-3403.
1150:(10): 6708-6714.
1035:(25): 5713-5716.
879:(22): 5553-5567.
409:Nonlinear optical
298:electronegativity
201:functional groups
194:Phosphaporphyrins
117:group 15 elements
76:electron carriers
1453:
1425:
1408:
1402:
1385:
1376:
1359:
1353:
1332:
1326:
1309:
1303:
1286:
1275:
1258:
1249:
1232:
1226:
1217:Chemistry Europe
1209:
1203:
1186:
1180:
1163:
1154:
1137:
1131:
1122:Pure Appl. Chem.
1114:
1103:
1099:(8): 1193-1204.
1086:
1069:
1052:
1039:
1022:
1013:
996:
990:
973:
964:
947:
941:
924:
913:
896:
883:
866:
849:
832:
817:
800:
787:
770:
753:
739:
730:
713:
707:
703:(4): 1344-1350.
690:
307:sterically bulky
294:Crystallographic
162:to yield Cl. PCl
61:transition metal
1461:
1460:
1456:
1455:
1454:
1452:
1451:
1450:
1431:
1430:
1429:
1428:
1409:
1405:
1393:Organometallics
1386:
1379:
1360:
1356:
1349:(3): 990-1002.
1339:
1333:
1329:
1310:
1306:
1287:
1278:
1259:
1252:
1233:
1229:
1210:
1206:
1187:
1183:
1164:
1157:
1138:
1134:
1115:
1106:
1087:
1072:
1053:
1042:
1030:Organic Letters
1023:
1016:
997:
993:
974:
967:
948:
944:
925:
916:
897:
886:
867:
852:
833:
820:
801:
790:
771:
756:
740:
733:
714:
710:
691:
680:
675:
650:
629:
596:
579:
574:
567:
563:
559:
534:
514:
482:
474:
421:
376:water-splitting
347:electrochemical
331:
291:
287:
279:
275:
271:
263:
259:
255:
245:
210:
206:
199:to two pyrrole
196:
189:
177:
173:
169:
165:
157:
130:
126:
113:
111:Phosphorus core
108:
17:
12:
11:
5:
1459:
1457:
1449:
1448:
1443:
1433:
1432:
1427:
1426:
1403:
1377:
1354:
1337:
1327:
1304:
1299:(3): 209-217.
1276:
1250:
1227:
1204:
1181:
1155:
1132:
1104:
1070:
1040:
1014:
991:
965:
942:
914:
884:
850:
845:(5): 746-754.
818:
788:
754:
731:
708:
677:
676:
674:
671:
649:
646:
628:
625:
595:
592:
578:
575:
573:
570:
565:
561:
557:
533:
530:
517:energy cascade
512:
481:
478:
472:
461:devices using
420:
417:
372:energy storage
368:photosynthetic
330:
327:
289:
285:
277:
273:
269:
261:
257:
253:
244:
241:
208:
204:
195:
192:
187:
175:
171:
167:
163:
155:
128:
124:
112:
109:
107:
104:
15:
13:
10:
9:
6:
4:
3:
2:
1458:
1447:
1444:
1442:
1439:
1438:
1436:
1424:
1420:
1417:
1413:
1407:
1404:
1401:
1397:
1394:
1390:
1384:
1382:
1378:
1375:
1371:
1368:
1364:
1358:
1355:
1352:
1348:
1345:
1341:
1331:
1328:
1325:
1321:
1318:
1314:
1308:
1305:
1302:
1298:
1295:
1291:
1285:
1283:
1281:
1277:
1274:
1270:
1267:
1263:
1257:
1255:
1251:
1248:
1244:
1241:
1237:
1231:
1228:
1225:
1221:
1218:
1214:
1208:
1205:
1202:
1199:: 1674-1675.
1198:
1195:
1191:
1185:
1182:
1179:
1176:: 9918-9921.
1175:
1172:
1168:
1162:
1160:
1156:
1153:
1149:
1146:
1142:
1136:
1133:
1130:
1126:
1123:
1119:
1113:
1111:
1109:
1105:
1102:
1098:
1095:
1091:
1085:
1083:
1081:
1079:
1077:
1075:
1071:
1068:
1065:: 1258-1271.
1064:
1061:
1057:
1051:
1049:
1047:
1045:
1041:
1038:
1034:
1031:
1027:
1021:
1019:
1015:
1012:
1009:: 1521â1529.
1008:
1005:
1001:
995:
992:
989:
986:, 8701-8709.
985:
982:
978:
972:
970:
966:
963:
959:
956:
952:
946:
943:
940:
936:
933:
929:
923:
921:
919:
915:
912:
908:
905:
901:
895:
893:
891:
889:
885:
882:
878:
875:
871:
865:
863:
861:
859:
857:
855:
851:
848:
844:
841:
837:
831:
829:
827:
825:
823:
819:
816:
812:
809:
805:
799:
797:
795:
793:
789:
786:
783:: 3868-3879.
782:
779:
775:
769:
767:
765:
763:
761:
759:
755:
752:
748:
744:
738:
736:
732:
729:
725:
722:
718:
712:
709:
706:
702:
699:
695:
689:
687:
685:
683:
679:
672:
666:
662:
660:
655:
647:
641:
637:
634:
627:Calixpyrroles
626:
624:
621:
620:Heck reaction
612:
608:
606:
602:
601:hybridization
593:
587:
583:
576:
571:
569:
564:, and Pt(dba)
549:
545:
543:
538:
531:
525:
521:
518:
510:
509:electrostatic
506:
502:
498:
494:
490:
486:
479:
477:
475:
468:
464:
460:
452:
448:
446:
445:reversibility
442:
438:
434:
430:
429:isomerization
426:
418:
416:
414:
410:
405:
404:excited state
401:
400:HOMO and LUMO
397:
393:
384:
380:
377:
373:
369:
364:
360:
355:
350:
348:
344:
343:spectroscopic
340:
336:
335:spectroscopic
328:
326:
324:
319:
315:
310:
308:
305:while large,
303:
299:
295:
283:
267:
251:
242:
240:
238:
227:
223:
221:
217:
214:
202:
193:
191:
184:
180:
161:
148:
144:
142:
138:
134:
122:
118:
110:
105:
99:
95:
93:
89:
85:
84:photochemical
81:
77:
74:
70:
66:
65:energy levels
62:
58:
55:
51:
47:
43:
39:
35:
31:
28:
24:
21:
1418:
1415:
1406:
1395:
1392:
1369:
1366:
1357:
1346:
1343:
1330:
1319:
1317:Biochemistry
1316:
1307:
1296:
1293:
1268:
1265:
1242:
1239:
1230:
1219:
1216:
1207:
1196:
1193:
1184:
1173:
1170:
1147:
1144:
1135:
1124:
1121:
1096:
1093:
1062:
1059:
1032:
1029:
1006:
1003:
994:
983:
980:
957:
954:
945:
934:
931:
906:
903:
876:
873:
842:
839:
810:
807:
780:
777:
746:
723:
720:
711:
700:
697:
659:antiaromatic
651:
633:heterocycles
630:
617:
597:
594:Calixphyrins
580:
554:
539:
535:
483:
467:ground state
459:Photovoltaic
457:
441:fluorescence
422:
389:
351:
332:
311:
246:
233:
216:condensation
197:
153:
135:solvent and
127:) added to H
114:
54:multidentate
22:
19:
18:
1127:: 583-593.
654:nonaromatic
648:Isophlorins
605:bond length
542:naphthalene
501:nucleotides
213:dehydration
141:hypervalent
92:coordinated
69:photoswitch
1446:Porphyrins
1435:Categories
673:References
532:Reactivity
433:wavelength
425:azobenzene
339:dicationic
243:Properties
179:counterion
42:phosphorus
30:polycyclic
27:conjugated
23:porphyrins
1145:ACS Omega
560:, Pd(dba)
437:quenching
413:chelating
363:red-shift
237:thiophene
230:materials
106:Synthesis
88:pnictogen
73:catalytic
46:phosphole
38:nitrogens
749:117-118
302:aromatic
183:halogens
181:. Other
137:alcohols
133:pyridine
34:pyrroles
556:Ni(cod)
505:guanine
439:of the
170:and KPF
57:ligands
493:cancer
476:cell.
392:UV-vis
314:phenyl
272:, -OCH
266:alkoxy
40:and a
268:(-OCH
256:, -CH
250:alkyl
166:/POCl
123:(POCl
394:and
282:aryl
252:(-CH
207:·OEt
80:ions
25:are
1419:130
1370:128
1347:130
1269:109
724:124
701:111
489:DNA
471:TiO
463:NiO
284:(-C
280:),
264:),
160:DCM
71:or
1437::
1414:.
1396:28
1391:.
1380:^
1365:.
1342:.
1320:43
1315:.
1297:87
1292:.
1279:^
1264:.
1253:^
1243:47
1238:.
1220:14
1215:.
1197:16
1192:.
1174:53
1169:.
1158:^
1143:.
1125:82
1120:.
1107:^
1097:42
1092:.
1073:^
1058:.
1043:^
1028:.
1017:^
1002:.
984:10
979:.
968:^
958:84
953:.
935:60
930:.
917:^
907:61
902:.
887:^
877:40
872:.
853:^
843:31
838:.
821:^
811:55
806:.
791:^
776:.
757:^
745:.
734:^
719:.
696:.
681:^
607:.
276:CH
260:CH
1338:2
1148:2
1063:7
1033:8
1007:2
781:3
566:2
562:2
558:2
513:2
473:2
290:5
288:H
286:6
278:3
274:2
270:3
262:3
258:2
254:3
209:2
205:3
188:3
176:6
172:6
168:3
164:3
156:2
129:2
125:3
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