Synthesis, structure, and nonlinear optical properties of diarylpolyynes

Organic Letters

Volumn 7, Issue 1, 2005, Pages 51-54

  Luu, Thanh ^a   Elliott, Erin ^a   Slepkov, Aaron D ^a   Eisler, Sara ^a   McDonald, Robert ^a   Hegmann, Frank A ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1,16 DIPHENYLHEXADECAOCTAYNE; ALKYNE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; HYPERPOLARIZATION; MOLECULE; POLARIMETRY; SOLID STATE; SYNTHESIS;

EID: 12344269243     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047931q     Document Type: Article

References (35)

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12. Synthetic and characterization details are provided as Supporting Information.
13. Caution: isolation of deprotected 1,3,5-hexatriynes should not be attempted as they can explode even at low temperature and in the absence of air; see ref 7.
14. 8, ATP) δ 134.4, 131.8, 129.7, 120.3, 79.1, 74.1, 67.9, 64.6, 63.8, 63.75, 63.72, 63.4.
15. A 3.0% yield for 3c had been reported by Armitage and co-workers; see ref 7.
16. Low temperature was necessary to prevent side reactions that likely arise from Castro - Stephens chemistry at the dibromoolefin groups: Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313-3315.
17. It is worth noting that octayne 5 was previously reported to be stable as a solid for only a period of hours when crystallized from ethyl acetate, perhaps the result of impurities remaining in the sample.
18. 2)]); CCDC 249138.
19. For an excellent review of solid-state characteristics of polyynes and parameters concerning topochemical polymerization, see: Szafert, S.; Gladysz, J. A. Chem. Rev. 2003, 103, 4175-4205.
20. See Supporting Information for details.
21. Primed atoms are related to unprimed ones via the crystallographic inversion center (0, 0, 0); double-primed atoms are related to unprimed ones via the inversion center (0, 1/2, 0).
22. 2)]); CCDC 249139.
23. Characterization of the product(s) from the heating of 3a and 3b is currently inconclusive, and further investigation is underway.
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26. Polyynes have been widely studied theoretically, inter alia: (a) Nalwa, H. S.; Mukai, J.; Kakuta, A. J. Phys. Chem. 1995, 99, 10766-10774. (b) Archibong, E. F.; Thakkar, A. J. J. Chem. Phys. 1993, 98, 8324-8329. (c) Buma, W. J.; Fanti, M.; Zerbetto, F. Chem. Phys. Lett. 1999, 313, 426-430. (d) Kuzyk, M. G. Phys. Rev. Lett. 2000, 85, 1218-1221. (e) Kuzyk, M. G. Opt. Lett. 2000, 25, 1183-1185; corrigenda 2003, 28, 135.
27. Polyynes have been widely studied theoretically, inter alia: (a) Nalwa, H. S.; Mukai, J.; Kakuta, A. J. Phys. Chem. 1995, 99, 10766-10774. (b) Archibong, E. F.; Thakkar, A. J. J. Chem. Phys. 1993, 98, 8324-8329. (c) Buma, W. J.; Fanti, M.; Zerbetto, F. Chem. Phys. Lett. 1999, 313, 426-430. (d) Kuzyk, M. G. Phys. Rev. Lett. 2000, 85, 1218-1221. (e) Kuzyk, M. G. Opt. Lett. 2000, 25, 1183-1185; corrigenda 2003, 28, 135.
28. Polyynes have been widely studied theoretically, inter alia: (a) Nalwa, H. S.; Mukai, J.; Kakuta, A. J. Phys. Chem. 1995, 99, 10766-10774. (b) Archibong, E. F.; Thakkar, A. J. J. Chem. Phys. 1993, 98, 8324-8329. (c) Buma, W. J.; Fanti, M.; Zerbetto, F. Chem. Phys. Lett. 1999, 313, 426-430. (d) Kuzyk, M. G. Phys. Rev. Lett. 2000, 85, 1218-1221. (e) Kuzyk, M. G. Opt. Lett. 2000, 25, 1183-1185; corrigenda 2003, 28, 135.
29. Polyynes have been widely studied theoretically, inter alia: (a) Nalwa, H. S.; Mukai, J.; Kakuta, A. J. Phys. Chem. 1995, 99, 10766-10774. (b) Archibong, E. F.; Thakkar, A. J. J. Chem. Phys. 1993, 98, 8324-8329. (c) Buma, W. J.; Fanti, M.; Zerbetto, F. Chem. Phys. Lett. 1999, 313, 426-430. (d) Kuzyk, M. G. Phys. Rev. Lett. 2000, 85, 1218-1221. (e) Kuzyk, M. G. Opt. Lett. 2000, 25, 1183-1185; corrigenda 2003, 28, 135.
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