[2 + 2] Photodimerization and photopolymerization of diphenylhexatriene crystals utilizing perfluorophenyl-phenyl stacking interactions

Journal of Fluorine Chemistry

Volumn 130, Issue 2, 2009, Pages 151-157

  Sonoda, Yoriko ^a   Goto, Midori ^a   Tsuzuki, Seiji ^a   Akiyama, Haruhisa ^a   Tamaoki, Nobuyuki ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

2 + 2 Photocycloaddition; Amorphous; Conjugated polyene; Crystal; Disorder; Non topochemical; Perfluorophenyl phenyl stacking interaction; Polarizing optical microscopy; Powder X ray diffraction

Indexed keywords

EID: 58649121697     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2008.09.010     Document Type: Article

References (39)

1. Ramamurthy V., and Venkatesan K. Chem. Rev. 87 (1987) 433-481
2. Tanaka K., and Toda F. Chem. Rev. 100 (2000) 1025-1074
3. Sonoda Y. In: Horspool W., and Lenci F. (Eds). CRC Handbook of Organic Photochemistry and Photobiology. 2nd ed. (2004), CRC Press, Boca Raton Chapter 73
4. Hoffmann N. Chem. Rev. 108 (2008) 1052-1103
5. MacGillivray L.R., Papaefstathiou G.S., Friščić T., Hamilton T.D., Bučar D.-K., Chu Q., Varshney D.B., and Georgiev I.G. Acc. Chem. Res. 41 (2008) 280-291
6. Hasegawa M. Adv. Phys. Org. Chem. 30 (1995) 117-171
7. Takahashi S., Miura H., Kasai H., Okada S., Oikawa H., and Nakanishi H. J. Am. Chem. Soc. 124 (2002) 10944-10945
8. Cohen M.D., Elgavi A., Green B.S., Ludmer Z., and Schmidt G.M.J. J. Am. Chem. Soc. 94 (1972) 6776-6779
9. Elgavi A., Green B.S., and Schmidt G.M.J. J. Am. Chem. Soc. 95 (1973) 2058-2059
10. Singh A.K., and Krishina T.S.R. J. Phys. Chem. A 101 (1997) 3066-3069
11. Liu J., Wendt N.L., and Boarman K.J. Org. Lett. 7 (2005) 1007-1010
12. Mori Y., and Matsumoto A. Chem. Lett. 36 (2007) 510-511
13. Sonoda Y., Miyazawa A., Hayashi S., and Sakuragi M. Chem. Lett. 30 (2001) 410-411
14. Hayashi S., and Sonoda Y. Bull. Chem. Soc., Jpn. 77 (2004) 2159-2164
15. Sonoda Y., Kawanishi Y., Ikeda T., Goto M., Hayashi S., Yoshida Y., Tanigaki N., and Yase K. J. Phys. Chem. B 107 (2003) 3376-3383
16. Sonoda Y., Kawanishi Y., and Goto M. Acta Crystallogr. C59 (2003) o311-o313
17. Reichenbächer K., Süss H.I., and Hulliger J. Chem. Soc. Rev. 34 (2005) 22-30
18. Naae D.G. Acta Crystallogr. B35 (1979) 2765-2768
19. Bartholomew G.P., Bu X., and Bazan G.C. Chem. Mater. 12 (2000) 2311-2318
20. Feast W.J., Lövenich P.W., Puschmann H., and Taliani C. Chem. Commun. (2001) 505-506
21. Ponzini F., Zagha R., Hardcastle K., and Siegel J.S. Angew. Chem. Int. Ed. 39 (2000) 2323-2325
22. Smith C.E., Smith P.S., Thomas R.L., Robins E.G., Collings J.C., Dai C., Scott A.J., Borwick S., Batsanov A.S., Watt S.W., Clark S.J., Viney C., Howard J.A.K., Clegg W., and Marder T.B. J. Mater. Chem. 14 (2004) 413-420
23. Coates G.W., Dunn A.R., Henling L.M., Ziller J.W., Lobkovsky E.B., and Grubbs R.H. J. Am. Chem. Soc. 120 (1998) 3641-3649
24. Coates G.W., Dunn A.R., Henling L.M., Dougherty D.A., and Grubbs R.H. Angew. Chem. Int. Ed. 36 (1997) 248-251
25. Xu R., Gramlich V., and Frauenrath H. J. Am. Chem. Soc. 128 (2006) 5541-5547
26. Sonoda Y., Goto M., Tsuzuki S., and Tamaoki N. J. Phys. Chem. A 111 (2007) 13441-13451
27. Korenaga T., Kadowaki K., and Sakai T. J. Fluorine Chem. 128 (2007) 557-561
28. Saltiel J., Sears D.F., Sun Y.P., and Choi J.O. J. Am. Chem. Soc. 114 (1992) 3607-3612
29. Adler G., and Reams W. J. Chem. Phys. 32 (1960) 1698-1700
30. Sonoda Y., Kawanishi Y., Tsuzuki S., and Goto M. J. Org. Chem. 70 (2005) 9755-9763
31. Shirota Y. J. Mater. Chem. 15 (2005) 75-93
32. Robinson M.R., Wang S., Heeger A.J., and Bazan G.C. Adv. Funct. Mater. 11 (2001) 413-419
33. Nakanishi F., Nakanishi H., Hasegawa M., and Yamada Y. J. Polym. Sci.: Polym. Chem. Ed. 13 (1975) 2499-2506
34. Frontera A., Quiñonero D., Costa A., Ballester P., and Deyà P.M. New J. Chem. 31 (2007) 556-560
35. Nakanishi H., Hasegawa M., and Mori T. Acta Crystallogr. C41 (1985) 70-71
36. Kim J.H., Matsuoka M., and Fukunishi K. Chem. Lett. 28 (1999) 143-144
37. Abdel-Mottaleb M.M.S., De Feyter S., Gesquière A., Sieffert M., Klapper M., Müllen K., and De Schryver F.C. Nano Lett. 1 (2001) 353-359
38. Xu L.-P., Yan C.-J., Wan L.-J., Jiang S.-G., and Liu M.-H. J. Phys. Chem. B 109 (2005) 14773-14778
39. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03 Revision C. 02 (2004), Gaussian Inc., Wallingford, CT