A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties

Masaru Kimura, Hideki Okamoto, Hisatoshi Kura, Ayumi Okazaki, Eiji Nagayasu, Kyosuke Satake, Shiro Morosawa, Masayoshi Fukazawa, Hamzer Abdel-Halim, D. O. Cowan

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16 Citations (Scopus)

Abstract

Electronic oxidative bisdecarboxylation of photoadducts of 2,5-dihalo-1,2-dihydrophthalic anhydride and anthracene gave the corresponding energy-rich heterodimers 12 and 13. The quantum yields of the formation of the excited anthracene from 12 and 13 by the irradiation of 280-nm light were 0.65 and 0.25, respectively. We assumed that the heterodimers of 12 and 13 form biradicaloid intermediates during thermal retro [4πs + 4πs] cycloaddition and consumed their stored energy without any visible light. However, we observed emission light from 340 to 460 nm through a glass filter and the formation of anthracene using Nd-YAG laser IR light (1.06 μm) by the multiphoton absorption, when fine powders of 12 and 13 were used.

Original languageEnglish
Pages (from-to)3908-3911
Number of pages4
JournalJournal of Organic Chemistry
Volume53
Issue number17
DOIs
Publication statusPublished - Aug 1 1988

ASJC Scopus subject areas

  • Organic Chemistry

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    Kimura, M., Okamoto, H., Kura, H., Okazaki, A., Nagayasu, E., Satake, K., Morosawa, S., Fukazawa, M., Abdel-Halim, H., & Cowan, D. O. (1988). A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties. Journal of Organic Chemistry, 53(17), 3908-3911. https://doi.org/10.1021/jo00252a004