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Sterically hindered diarylethenes with a benzobis(thiadiazole) bridge: photochemical and kinetic studies
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
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2015 (English)In: Journal of Materials Chemistry C, ISSN 2050-7526, Vol. 3, no 33, 8665-8674 p.Article in journal (Refereed) Published
Abstract [en]

Four rationally designed diarylethenes (DAEs) 1-4 with a benzobis(thiadiazole) bridge are specifically designed for gaining insights into steric effects on photochromic performances. It is shown that, upon increasing steric hindrance, the exchanging rate between two main conformers in the ring-open form gradually slows down, offering the opportunity for isolating photoactive anti-parallel conformers. Impressively, the separated anti-parallel conformer shows high cyclization quantum yields over the unresolved common DAEs. The typical donor-pi-acceptor (D-pi-A) feature in ring-open DAEs 1-4 endows their prominent fluorescence, which can be conveniently modulated by photocyclization. In the ring-closed form, the excess steric hindrance is found to seriously disrupt the thermal bistability, and particularly 3c fades quickly with a half-life of several hours at ambient temperature. In contrast, both 1c and 2c exhibit excellent stability, which originates from the stabilization effects of intramolecular hydrogen bonds. This work demonstrates the steric effects on the photochemical and kinetic behaviors of DAEs, providing a unique approach to develop photochromic DAEs with high photosensitivity.

Place, publisher, year, edition, pages
2015. Vol. 3, no 33, 8665-8674 p.
National Category
Physical Sciences
URN: urn:nbn:se:kth:diva-173294DOI: 10.1039/c5tc01796cISI: 000359565300027ScopusID: 2-s2.0-84939144462OAI: diva2:852545

QC 20150909

Available from: 2015-09-09 Created: 2015-09-09 Last updated: 2015-09-09Bibliographically approved

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Li, XinÅgren, Hans
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