Dihydroazulene‐Azobenzene‐Dihydroazulene Triad Photoswitches
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Photoswitch triads comprising two dihydroazulene (DHA) units in conjugation with a central trans-azobenzene (AZB) unit were prepared in stepwise protocols starting from meta- and para-disubstituted azobenzenes. The para-connected triad had significantly altered optical properties and lacked the photoactivity of the separate photochromes. In contrast, for the meta-connected triad, all three photochromes could be photoisomerized to generate an isomer with two vinylheptafulvene (VHF) units and a cis-azobenzene unit. Ultrafast spectroscopy of the photoisomerizations revealed a fast DHA-to-VHF photoisomerization and a slower trans-to-cis AZB photoisomerization. This meta triad underwent thermal VHF-to-DHA back-conversion with a similar rate of all VHFs, independent of the identity of the neighboring units, and in parallel thermal cis-to-trans AZB conversion. The experimental observations were supported by computation (excitation spectra and orbital analysis of the transitions).
Original language | English |
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Journal | Chemistry: A European Journal |
Volume | 27 |
Issue number | 48 |
Pages (from-to) | 12437-12446 |
Number of pages | 10 |
ISSN | 0947-6539 |
DOIs | |
Publication status | Published - 2021 |
ID: 271820297