Synthesis and characterization of oligo(2,7-biphenylenylene-(E)-vinylene)s

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5913-5916

  Kwong, Chi Yuen ^b   Leung, Man Kit ^a,b   Lin, Shi Chun ^a   Chan, Tze Lock ^b   Chow, Hak Fun ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CIS TRANS ISOMERISM; CONJUGATION; ELECTROCHEMISTRY; EPOXIDATION; LUMINESCENCE; POLYMERIZATION; SPECTROSCOPY; SYNTHESIS;

EID: 0004502055     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01275-0     Document Type: Article

References (17)

1. 1. Auchter-Krummel, P.; Müllen, K. Angew. Chem. Int. Ed. Engl., 1991, 30, 1003.
2. 2. For general reviews of biphenylene chemistry, see (a) Barton, J. W. "Non-benzenoid Aromatics, " Vol. 1, Academic Press, New York. 1969, 32.
3. (b) Lloyd, D. 'Non-benzenoid Conjugated Carbocyclic Compounds," Elsevier, Amsterdam, 1984, 216.
4. (c) Vögtle, F. "Fascinating Molecules in Organic Chemistry." Wiley, New York. 1992, 111.
5. 3. (a) Hanson, M. P. ; Marvel, C. S. J. Polymer Science: Polymer Lett. Ed. 1978, 16, 653.
6. (b) Lin S. C.; Marvel, C. S. J. Polymer Science: Polymer Chem. Ed. 1979, 17, 2337.
7. 4. Chan, T. L.; Fong, S.; Li, Y.; Man T.-O.; Poon, C.-D. J. Chem. Soc., Chem. Commun., 1994, 1771.
8. 5. Chan, T. L.; Chow, H. F.; Fong, S.; Leung M.-k.; Tu, J. J. Chem. Soc., Chem. Commun., 1994, 1919.
9. C (only 26 carbon signals were observed for OBPV 3) 31.48, 34.89, 114.26, 114.31, 114.43, 117.52, 117.61, 120.84, 122.14, 128.05, 128.16, 128.34, 128.44, 128.59, 128.64, 129.08, 136.57, 137.84, 137.96, 138.31, 149.81, 150.08, 150.19, 150.81, 150.90, 151.13.
10. 7. (a) Trost, B. M.; Curran, D. P. Tetrahedron Lett., 1981, 22, 1287.
11. (b) Trost, B. M.; Braslau, R. J. Org. Chem., 1988, 53, 532.
12. 8. By reaction of 5 with thiourea, followed by NaOH hydrolysis, 2,7-(bismercaptomethyl)biphenylene was obtained in moderated yield.
13. 9. Tolbert, L. M. Acc. Chem. Res., 1992, 25, 561 and references cited therein.
14. 10. Extrapolated from the data reported in the following papers: (1) Schenk, R.; Gregorius, H.; Müllen, K. Adv. Mater. 1991, 3, 492.
15. (c) Schenk, R.; Gregorius, H.; Meerholz, K.; Heinze, J.; Müllen, K. J. Am. Chem. Soc., 1991, 113, 2634.
16. 4 (0.1M) as the supporting electrolyte. (table presented)
17. 12. Schenk, R.; Gregorius, H.; Müllen, K.; Heinze, J. Adv. Mater. 1994, 6, 671.