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Substitution effect on the photochromic properties of benzo[b]thiophene-1,1-dioxide based diarylethenes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
2015 (English)In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 5, no 106, 87626-87634 p.Article in journal (Refereed) Published
Abstract [en]

Benzo[b]thiophene-1,1-dioxide based diarylethenes (DAEs), BTT-1 to BTT-4, containing methyl, phenyl, formyl and triphenylamine groups at the 5,5'-position of the thiophene rings have been developed for gaining an insight into the substituent effect on the absorption and photochromic properties. Electron-donating substituents, such as phenyl and triphenylamine groups, are found to be effective at shifting the absorption band to a longer wavelength and decreasing the cyclization quantum yield. The electron-withdrawing formyl group can increase the cyclization quantum yield, but it reduces the thermal stability of the ring-closed isomer to some extent. BTT-4 bearing a triphenylamine group shows the poorest fatigue resistance among these four compounds, which is possibly due to the larger extended pi-conjugation length in the ring-closed isomer. BTT-2 bearing a phenyl unit undergoes typical photochromic reaction not only in solution, but also in PMMA thin film and in bulky crystals with excellent fatigue resistance and thermal stability.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2015. Vol. 5, no 106, 87626-87634 p.
Keyword [en]
Ethene Bridge; Hindered Diarylethenes; Molecular Switch; Logic Gates; Bisthienylethene; Derivatives; Light; Dithienylethenes; Photocyclization; Naphthalimide
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-176999DOI: 10.1039/c5ra18116jISI: 000363233500089ScopusID: 2-s2.0-84945249582OAI: diva2:870271

QC 20151113

Available from: 2015-11-13 Created: 2015-11-13 Last updated: 2015-11-13Bibliographically approved

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