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On the Charge-Transfer Excitations in Azobenzene Maleimide Compounds: A Theoretical Study
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Number of Authors: 72019 (English)In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 123, no 26, p. 5525-5536Article in journal (Refereed) Published
Abstract [en]

Photoswitchable systems with charge-transfer (CT) transitions have gained much attention during the recent years because of their many emerging applications. CT transitions themselves are of fundamental importance from physical, chemical, engineering, and molecular modeling points of view because they depend on the modified intramolecular electronic structure. CT transitions in azobenzene (AB) were observed when substituted with the maleimide (MI) functional group. This work represents a systematic theoretical study of excited states of the AB MI structures of eight azo derivatives. In addition to the two main azo transitions (pi -> pi* and n -> pi*), our calculations show a CT occurring between the azo moiety as a donor and the MI group as an acceptor. The CT mechanism can be characterized based on both the number and the position of the MI fragments. MI groups in the azo structure result in low-energy transitions, changing the order of the main transitions by introducing a CT character. Calculations using both density functional theory (DFT) and high-end molecular orbital theories confirm the CT character of these derivatives, although the order of excited states was found to differ depending on the chosen level of theory. We present here the first theoretical investigation of the electronic excited states (n pi*CT and pi pi*CT) and corresponding transitions for this class of compounds. The computational results showed that the CT mechanism in AB MI derivatives can occur via two pathways: planar and twisted. Our findings are expected to be of substantial interest, especially in the area of molecular optoelectronics and in the design of responsive materials.

Place, publisher, year, edition, pages
2019. Vol. 123, no 26, p. 5525-5536
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Chemical Sciences
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URN: urn:nbn:se:su:diva-171764DOI: 10.1021/acs.jpca.9b02082ISI: 000474796100011PubMedID: 31244120OAI: oai:DiVA.org:su-171764DiVA, id: diva2:1346575
Available from: 2019-08-28 Created: 2019-08-28 Last updated: 2019-08-28Bibliographically approved

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