Iterative synthesis and properties of cross-conjugated iso- polydiacetylene oligomers

Journal of the American Chemical Society

Volumn 121, Issue 2, 1999, Pages 458-459

  Zhao, Yuming ^a   Tykwinski, Rik R ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; POLYDIACETYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ELECTRICITY; ELECTRON TRANSPORT; LUMINESCENCE; OLIGOMERIZATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0033585534     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983288p     Document Type: Article

References (37)

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21. Polydiacetylenes; Bloor, D., Chance, R. R., Eds.; Martinus Nijhoff: Dordrecht, 1985. Wudl, F.; Bitler, S. P. J. Am. Chem. Soc. 1986, 108, 4685-4687. Giesa, R.; Klapper, M.; Schulz, R. C. Makromol. Chem., Macromol. Symp. 1991, 44, 1-10. Giesa, R.; Schulz, R. C. Polym. Int. 1994, 33, 43-60.
22. Polydiacetylenes; Bloor, D., Chance, R. R., Eds.; Martinus Nijhoff: Dordrecht, 1985. Wudl, F.; Bitler, S. P. J. Am. Chem. Soc. 1986, 108, 4685- 4687. Giesa, R.; Klapper, M.; Schulz, R. C. Makromol. Chem., Macromol. Symp. 1991, 44, 1-10. Giesa, R.; Schulz, R. C. Polym. Int. 1994, 33, 43-60.
23. Polydiacetylenes; Bloor, D., Chance, R. R., Eds.; Martinus Nijhoff: Dordrecht, 1985. Wudl, F.; Bitler, S. P. J. Am. Chem. Soc. 1986, 108, 4685- 4687. Giesa, R.; Klapper, M.; Schulz, R. C. Makromol. Chem., Macromol. Symp. 1991, 44, 1-10. Giesa, R.; Schulz, R. C. Polym. Int. 1994, 33, 43-60.
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27. Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proc. Int. 1995, 27, 127-160.
28. 13C NMR, IR, UV, MS, and either EA or HRMS (except 13). Details are provided as Supporting Information.
29. For the synthesis of a related molecule, see: Boldi, A. M.; Anthony, J.; Gramlich, V.; Knobler, C. B.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Diederich, F. Helv. Chim. Acta 1995, 78, 779-796.
30. 2 using Macromodel 5.5.
31. 2)]. Details are provided as Supporting Information.
32. A cyclic hexameric oligomer, constrained to a cisoid ene-yne-ene orientation, shows only one low energy absorption at 285 nm (ref 22).
33. Eisler, S.; Tykwinski, R. R., manuscript in preparation.
34. Anthony, J.; Boldi, A. M.; Boudon, C.; Gisselbrecht, J.-P.; Gross, M.; Seiler, P.; Knobler, C. B.; Diederich, F. Helv. Chim. Acta 1995, 78, 797-817.
35. Contributions from homoconjugation as measured by UV-vis spectroscopy appear negligible as determined by comparison to a cyclic, hexameric analogue. The more rigid cyclic oligomer, constrained to an orientation nearly optimal for overlap of the in-plane sp-orbitals of the acetylenic units, shows no enhanced π-electron delocalization attributable to homoconjugation (ref 22).
36. Similar bathochromic shifts as a function of oligomer length were observed in hexane and THF.
37. -3 M) were all consistent suggesting negligible aggregation of the oligomers in chloroform.