Systematic study on the thermal cycloreversion reactivity of diarylethenes with alkoxy and alkyl groups at the reactive carbons

Systematic study on the thermal cycloreversion reactivity of diarylethenes with alkoxy and alkyl... The relationship between the thermal cycloreversion reactivity of diarylethenes and the bulkiness of the substituents at the reactive carbons was systematically investigated. Two photochromic diarylethenes, 1,2-bis(2-isobutoxy-5-phenyl-3-thienyl)perfluorocyclopentene (1a) and 1,2-bis(2-neopentoxy-5-phenyl-3-thienyl)perfluorocyclopentene (2a), were newly synthesized and their optical properties and thermal cycloreversion reactivity were examined, because there is insufficient data for diarylethenes with alkoxy groups at the reactive carbons. The steric substituent constant was employed to correlate the relationship between the thermal cycloreversion reactivity of diarylethenes with alkyl and alkoxy groups at the reactive carbons and the bulkiness of the substituent. A good correlation was obtained for the substituent constant using CH2 instead of oxygen in the alkoxy groups. The results indicate that this is a very useful strategy for the design of novel diarylethenes with desired thermal cycloreversion reactivity. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Systematic study on the thermal cycloreversion reactivity of diarylethenes with alkoxy and alkyl groups at the reactive carbons

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Publisher
Springer Netherlands
Copyright
Copyright © 2012 by Springer Science+Business Media B.V.
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0648-0
Publisher site
See Article on Publisher Site

Abstract

The relationship between the thermal cycloreversion reactivity of diarylethenes and the bulkiness of the substituents at the reactive carbons was systematically investigated. Two photochromic diarylethenes, 1,2-bis(2-isobutoxy-5-phenyl-3-thienyl)perfluorocyclopentene (1a) and 1,2-bis(2-neopentoxy-5-phenyl-3-thienyl)perfluorocyclopentene (2a), were newly synthesized and their optical properties and thermal cycloreversion reactivity were examined, because there is insufficient data for diarylethenes with alkoxy groups at the reactive carbons. The steric substituent constant was employed to correlate the relationship between the thermal cycloreversion reactivity of diarylethenes with alkyl and alkoxy groups at the reactive carbons and the bulkiness of the substituent. A good correlation was obtained for the substituent constant using CH2 instead of oxygen in the alkoxy groups. The results indicate that this is a very useful strategy for the design of novel diarylethenes with desired thermal cycloreversion reactivity.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jun 19, 2012

References

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