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 › peer-review

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

Access to Document

10.1021/jo00252a004

Fingerprint Dive into the research topics of 'A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties'. Together they form a unique fingerprint.

Cite this

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 › peer-review

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.

@article{c7e73410adf74fb1b1cd9373ec85b846,

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

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.",

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

year = "1988",

month = aug,

day = "1",

doi = "10.1021/jo00252a004",

language = "English",

volume = "53",

pages = "3908--3911",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - A Desirable Route to Heterodimers of 1,4-Dihalobenzenes and Anthracene and Their Photoproperties and Thermal Properties

AU - Kimura, Masaru

AU - Okamoto, Hideki

AU - Kura, Hisatoshi

AU - Okazaki, Ayumi

AU - Nagayasu, Eiji

AU - Satake, Kyosuke

AU - Morosawa, Shiro

AU - Fukazawa, Masayoshi

AU - Abdel-Halim, Hamzer

AU - Cowan, D. O.

PY - 1988/8/1

Y1 - 1988/8/1

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0000463883&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000463883&partnerID=8YFLogxK

U2 - 10.1021/jo00252a004

DO - 10.1021/jo00252a004

M3 - Article

AN - SCOPUS:0000463883

VL - 53

SP - 3908

EP - 3911

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 17

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this