91:
362:
1020:
Yang, W. L.; Fabbri, J. D.; Willey, T. M.; Lee, J. R. I.; Dahl, J. E.; Carlson, R. M. K.; Schreiner, P. R.; Fokin, A. A.; Tkachenko, B. A.; Fokina, N. A.; Meevasana, W.; Mannella, N.; Tanaka, K.; Zhou, X.-J.; van Buuren, T.; Kelly, M. A.; Hussain, Z.; Melosh, N. A.; Shen, Z.-X. (2007).
621:
Dahl, J. E. P.; Moldowan, J. M.; Peakman, T. M.; Clardy, J. C.; Lobkovsky, E.; Olmstead, M. M.; May, P. W.; Davis, T. J.; Steeds, J. W.; Peters, K. E.; Pepper, A.; Ekuan, A.; Carlson, R. M. K. (2003). "Isolation and
Structural Proof of the Large Diamond Molecule, Cyclohexamantane
465:
fluids (volatile oils, condensates and wet gases). These fluids can have up to a spoonful of diamondoids per US gallon (3.78 liters). A review by Mello and
Moldowan in 2005 showed that although the carbon in diamonds is not biological in origin, the diamondoids found in
696:
Zhang, J.; Zhu, Z.; Feng, Y.; Ishiwata, H.; Miyata, Y.; Kitaura, R.; Dahl, J. E.; Carlson, R. M.; Fokina, N. A.; Schreiner, P. R.; Tománek, D.; Shinohara, H. (Mar 25, 2013). "Evidence of diamond nanowires formed inside carbon nanotubes from diamantane dicarboxylic acid".
768:
Fokin, Andrey A.; Schreiner, Peter R.; Fokina, Natalie A.; Tkachenko, Boryslav A.; Hausmann, Heike; Serafin, Michael; Dahl, Jeremy E. P.; Liu, Shenggao; Carlson, Robert M. K. (2006). "Reactivity of
Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond".
732:
Tkachenko, Boryslav A.; Fokina, Natalie A.; Chernish, Lesya V.; Dahl, Jeremy E. P.; Liu, Shenggao; Carlson, Robert M. K.; Fokin, Andrey A.; Schreiner, Peter R. (2006). "Functionalized
Nanodiamonds Part 3: Thiolation of Tertiary/Bridgehead Alcohols".
288:
reaction to attach cyclopentane rings. Longer diamondoids have been formed from diamantane dicarboxylic acid. The first-ever isolation of a wide range of diamondoids from petroleum took place in the following steps: a
77:
deposits and have been extracted and purified into large pure crystals of polymantane molecules having more than a dozen adamantane cages per molecule. These species are of interest as molecular approximations of the
90:
301:
at 400 to 450 °C in order to remove all non-diamondoid compounds (diamondoids are thermodynamically very stable and will survive this pyrolysis) and then a series of
73:, and higher polymantanes) as well as numerous isomeric and structural variants of adamantanes and polymantanes. These diamondoids occur naturally in
912:
Drummond, N. D.; Williamson, A. J.; Needs, R. J.; Galli, G. (2005). "Electron emission from diamondoids: a diffusion quantum Monte Carlo study".
805:
665:
Burns, W.; McKervey, M. A.; Mitchell, T. R.; Rooney, J. J. (1978). "A New
Approach to the Construction of Diamondoid Hydrocarbons. Synthesis of
1080:
483:
302:
1125:
502:. Due to their well-defined size and structure diamondoids also serve as a model system for electronic structure calculations.
973:
Willey, T. M.; Bostedt, C.; van Buuren, T.; Dahl, J. E.; Liu, S. G.; Carlson, R. M. K.; Terminello, L. J.; Möller, T. (2005).
517:. As a result, the energy of the lowest unoccupied molecular orbital is roughly independent of the size of the diamondoid.
1120:
1106:
Diamondoid-functionalized gold nanogaps as sensors for natural, mutated, and epigenetically modified DNA nucleotides
543:
442:
1101:
Diamondoid
Molecules: With Applications in Biomedicine, Materials Science, Nanotechnology & Petroleum Science
1022:
294:
1085:
327:. The medial position (base) in this molecule (the isomer pentamantane) is calculated to yield a more favorable
317:
361:
525:
505:
Many of the optoelectronic properties of diamondoids are determined by the difference in the nature of the
450:
1095:
470:
are composed of carbon from biological sources. This was determined by comparing the ratios of carbon
1037:
986:
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883:
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389:
352:
290:
107:
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921:
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499:
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and higher. The spectrum of each diamondoid is found to reflect its individual size, shape and
1055:
1002:
947:
852:
825:"Optical Response of Diamond Nanocrystals as a Function of Particle Size, Shape, and Symmetry"
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Landt, L.; Klünder, K.; Dahl, J. E.; Carlson, R. M. K.; Möller, T.; Bostedt, C. (2009).
1090:
370:
1114:
538:
514:
400:
79:
959:
607:
848:
495:
998:
943:
572:"Isolation and Structure of Higher Diamondoids, Nanometer-Sized Diamond Molecules"
487:
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332:
328:
103:
70:
895:
231:
156:
117:
99:
95:
66:
39:
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Vörös, M.; Gali, A. (2009). "Optical absorption of diamond nanocrystals from
1050:
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975:"Molecular Limits to the Quantum Confinement Model in Diamond Clusters"
471:
382:
340:
51:
782:
746:
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Cluster and
Nanocrystal Research Group, Technische Universität Berlin
312:
groups at the bridgehead positions. This allows their anchorage to a
214:
186:. Diamantane has four identical faces available for anchoring a new C
131:
35:
280:
One tetramantane isomer is the largest ever diamondoid prepared by
926:
434:
309:
1023:"Monochromatic Electron Photoemission from Diamondoid Monolayers"
217:. One of these isomers displays a helical twist and is therefore
1096:
Electronic and
Optical Properties of Diamondoids (free download)
313:
570:
Dahl, J. E.; Liu, S. G.; Carlson, R. M. K. (3 January 2003).
360:
89:
433:
and in a series of steps (not shown) to the corresponding
507:
highest occupied and lowest unoccupied molecular orbitals
245:
and one more pentamantane exists with chemical formula C
1091:
388:
as an intermediate which is hydrolysed to the apical
237:
Pentamantane has nine isomers with chemical formula C
308:
In one study a tetramantane compound is fitted with
520:Diamondoids have been found to exhibit a negative
205:). Triamantane has eight faces on to which a new C
1086:Nanotechnology and the arrival of the Diamond Age
907:
905:
461:Diamondoids are found in mature high-temperature
323:Organic chemistry of diamondoids even extends to
1081:Molecular Diamond Technologies, Chevron Texaco
343:exclusively gives the medial bromo derivative
8:
65:may include one or more cages (adamantane,
50:), the smallest unit cage structure of the
331:than the apical position (top) and simple
1049:
925:
806:"Petroleum: To Be Or Not To Be Abiogenic"
589:
671:Journal of the American Chemical Society
453:to the bromide but without selectivity.
27:Various forms of carbon crystal lattices
699:Angewandte Chemie International Edition
632:Angewandte Chemie International Edition
559:
804:Mello, M. R.; Moldowan, J. M. (2005).
565:
563:
303:high-performance liquid chromatography
82:framework, terminated with C−H bonds.
486:for all diamondoids lies deep in the
425:species. This alcohol can react with
7:
524:, making them potentially useful in
213:unit can be added resulting in four
437:. Pentamantane can also react with
874:density-functional calculations".
293:above 345 °C, the equivalent
25:
478:Optical and electronic properties
347:which on hydrolysis in water and
771:The Journal of Organic Chemistry
94:Diamondoids, from left to right
849:10.1103/PhysRevLett.103.047402
537:Other diamond-like compounds:
1:
999:10.1103/PhysRevLett.95.113401
944:10.1103/PhysRevLett.95.096801
490:spectral region with optical
57:. Diamondoids also known as
34:are generalizations of the
1142:
896:10.1103/PhysRevB.80.161411
544:Abiogenic petroleum origin
513:, whereas the latter is a
1126:Adamantane-like molecules
318:self-assembled monolayers
316:surface and formation of
295:atmospheric boiling point
981:(Submitted manuscript).
1051:10.1126/science.1141811
979:Physical Review Letters
914:Physical Review Letters
829:Physical Review Letters
591:10.1126/science.1078239
305:separation techniques.
38:cage molecule known as
711:10.1002/anie.201209192
644:10.1002/anie.200250794
366:
171:, two face-fused cages
110:
985:(11): 113401–113404.
457:Origin and occurrence
451:free radical reaction
449:bromide (TBABr) in a
364:
93:
63:condensed adamantanes
1121:Carbon nanoparticles
920:(9): 096801–096804.
810:Search and Discovery
234:have been separated.
1042:2007Sci...316.1460Y
1036:(5830): 1460–1462.
991:2005PhRvL..95k3401W
936:2005PhRvL..95i6801D
888:2009PhRvB..80p1411V
841:2009PhRvL.103d7402L
683:10.1021/ja00471a041
365:Pentamane chemistry
320:(diamond-on-gold).
291:vacuum distillation
268:Super-adamantane (C
255:Cyclohexamantane (C
509:: the former is a
484:optical absorption
395:due to the higher
367:
197:Isotetramantane (C
113:Examples include:
111:
106:and one isomer of
876:Physical Review B
783:10.1021/jo061561x
777:(22): 8532–8540.
747:10.1021/ol053136g
705:(13): 3717–3721.
638:(18): 2040–2044.
526:electron-emission
522:electron affinity
439:tetrabromomethane
381:gives the apical
282:organic synthesis
16:(Redirected from
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335:of pentamantane
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584:(5603): 96–99.
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427:thionyl bromide
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55:crystal lattice
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1070:External links
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882:(16): 161411.
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741:(9): 1767–70.
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447:-butylammonium
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515:surface state
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184:triadamantane
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369:In contrast
368:
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325:pentamantane
324:
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169:diadamantane
168:
112:
108:tetramantane
62:
59:nanodiamonds
58:
31:
29:
488:ultraviolet
379:nitric acid
333:bromination
329:carbocation
232:enantiomers
104:triamantane
71:triamantane
32:diamondoids
18:Triamantane
1115:Categories
555:References
511:bulk state
351:forms the
157:Diamantane
118:Adamantane
100:diamantane
96:adamantane
67:diamantane
40:adamantane
927:0801.0381
872:ab initio
549:Nanorobot
528:devices.
494:around 6
492:band gaps
474:present.
468:petroleum
463:petroleum
299:pyrolysis
286:carbenoid
219:prochiral
75:petroleum
1060:17556579
1007:16197003
960:16703233
952:16197235
857:19659398
791:17064030
755:16623546
719:23418054
652:12746817
608:46688135
600:12459548
532:See also
500:symmetry
472:isotopes
182:), also
86:Examples
1038:Bibcode
1030:Science
987:Bibcode
932:Bibcode
884:Bibcode
837:Bibcode
577:Science
390:alcohol
383:nitrate
353:alcohol
341:bromine
297:, then
215:isomers
167:) also
145:BC-8 (C
52:diamond
1058:
1005:
958:
950:
855:
789:
753:
717:
650:
606:
598:
443:tetra-
221:. The
132:Iceane
36:carbon
1026:(PDF)
956:S2CID
922:arXiv
604:S2CID
435:thiol
377:with
339:with
310:thiol
194:unit.
1056:PMID
1003:PMID
948:PMID
853:PMID
787:PMID
751:PMID
715:PMID
667:anti
648:PMID
630:)".
596:PMID
482:The
441:and
314:gold
226:and
1046:doi
1034:316
995:doi
940:doi
892:doi
845:doi
833:103
779:doi
743:doi
707:doi
679:doi
675:100
640:doi
586:doi
582:299
415:HNO
373:of
349:DMF
61:or
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622:(C
602:.
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562:^
404:NO
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261:30
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120:(C
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393:5
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337:1
276:)
272:H
263:)
259:H
249:H
241:H
228:M
224:P
211:4
209:H
207:4
201:H
192:4
190:H
188:4
178:H
163:H
153:)
149:H
142:)
138:H
128:)
124:H
46:H
20:)
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