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Synthesis of Novel Thermally Irreversible Photochromic 1-Aryl-1,3-butadiene Derivatives

Synthesis of Novel Thermally Irreversible Photochromic 1-Aryl-1,3-butadiene Derivatives A new thermally irreversible photochromic compound, 3,3,4,4,5,5-hexafluoro-1-(1-isopropylidene-1-phenylmethyl)-2-(2,4,5-trimethyl-3-thienyl)cyclopentene 3O, was synthesized and its photochromic properties were examined. It showed thermally irreversible photochromism. While 3O is colorless, it turned yellow (λmax 445 nm) upon the irradiation of 313-nm light, caused by the generation of 3C as the result of photochemical 6π-electrocyclization. It returned to the initial colorless state by 405-nm light irradiation. The coloration and decoloration quantum yields with 313-nm light were 0.43 and 0.14, respectively, and the decoloration quantum yield with 405-nm light was 0.16. The colored form 3C in a PMMA film did not fade when stored at 80 °C for more than one month, and the fatigue resistivity in the PMMA film for iterative irradiation was excellent. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Bulletin of the Chemical Society of Japan Oxford University Press

Synthesis of Novel Thermally Irreversible Photochromic 1-Aryl-1,3-butadiene Derivatives

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References (4)

Publisher
Oxford University Press
Copyright
© 2003 The Chemical Society of Japan
ISSN
0009-2673
eISSN
1348-0634
DOI
10.1246/bcsj.76.363
Publisher site
See Article on Publisher Site

Abstract

A new thermally irreversible photochromic compound, 3,3,4,4,5,5-hexafluoro-1-(1-isopropylidene-1-phenylmethyl)-2-(2,4,5-trimethyl-3-thienyl)cyclopentene 3O, was synthesized and its photochromic properties were examined. It showed thermally irreversible photochromism. While 3O is colorless, it turned yellow (λmax 445 nm) upon the irradiation of 313-nm light, caused by the generation of 3C as the result of photochemical 6π-electrocyclization. It returned to the initial colorless state by 405-nm light irradiation. The coloration and decoloration quantum yields with 313-nm light were 0.43 and 0.14, respectively, and the decoloration quantum yield with 405-nm light was 0.16. The colored form 3C in a PMMA film did not fade when stored at 80 °C for more than one month, and the fatigue resistivity in the PMMA film for iterative irradiation was excellent.

Journal

Bulletin of the Chemical Society of Japan – Oxford University Press

Published: Feb 15, 2003

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