Photo- and ionochromic properties of aza crown derivatives of enamino 1-benzothiophen-2-ones View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2014-04

AUTHORS

V. I. Minkin, V. A. Bren’, A. D. Dubonosov, K. S. Tikhomirova, E. N. Shepelenko

ABSTRACT

2-(N-Acyl-N-arylaminomethylidene)-1-benzothiophen-3(2H)-ones exhibit photochromic properties due to photoinitiated Z/E isomerization with respect to the exocyclic C=C bond and subsequent fast thermal N→O migration of the acyl group and syn→anti isomerization of the N-acyl isomer. Introduction of a 15-azacrown-5 substituent into the para position of the aryl group reduces the quantum yield of the N→O rearrangement down to zero. By contrast, under irradiation with a mercury lamp, crown ether complexes with alkaline earth cations are converted almost completely into the O-acyl isomers which, unlike their N-acyl analogs, show no fluorescence. The highest quantum yields for the N→O acyl group migration are observed for the calcium complexes. The obtained compounds constitute a new class of acylotropic molecular switches operating under photoinitiation exclusively in the presence of alkaline earth cations. More... »

PAGES

540-543

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428014040162

DOI

http://dx.doi.org/10.1134/s1070428014040162

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1041954205


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