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

doi:10.1021/jo00252a004

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

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	3908-3911
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	53
Issue number	17
DOIs	https://doi.org/10.1021/jo00252a004
Publication status	Published - Aug 1 1988

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo00252a004

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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

A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties. / Kimura, Masaru; Okamoto, Hideki; Kura, Hisatoshi; Okazaki, Ayumi; Nagayasu, Eiji; Satake, Kyosuke; Morosawa, Shiro; Fukazawa, Masayoshi; Abdel-Halim, Hamzer; Cowan, D. O.

In: Journal of Organic Chemistry, Vol. 53, No. 17, 01.08.1988, p. 3908-3911.

Research output: Contribution to journal › Article

Kimura, Masaru ; Okamoto, Hideki ; Kura, Hisatoshi ; Okazaki, Ayumi ; Nagayasu, Eiji ; Satake, Kyosuke ; Morosawa, Shiro ; Fukazawa, Masayoshi ; Abdel-Halim, Hamzer ; Cowan, D. O. / A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties. In: Journal of Organic Chemistry. 1988 ; Vol. 53, No. 17. pp. 3908-3911.

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AB - 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.

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