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The Malleable Excited States of Benzothiadiazole Dyes and Investigation of their Potential for Photochemical Control
Author(s) -
Warner Caroline C.,
Thooft Andrea M.,
Norris Sean R.,
Lampkin Bryan J.,
Demirci Selin K.,
VanVeller Brett
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001980
Subject(s) - excited state , photochemistry , solvent , chemistry , excitation , ring (chemistry) , organic chemistry , atomic physics , physics , quantum mechanics
A new design strategy to control the efficiency of a photocleavage reaction based on changing the nature of the excited state is presented. A novel class of photoactive compounds has been synthesized by combining the classical o ‐nitrobenzyl scaffold with an environmentally sensitive dye, 4‐amino‐nitrobenzothiazole. Irradiation in a polar solvent led to an excited state that was inoperative for photochemistry whereas excitation in a nonpolar solvent led to an excited state that was photochemically active. While our design hypothesis tests true for the on/off control of a photochemical process, an alternative photochemical ring‐opening of the heterocycle appears to be the preferred process in contrast to the intended photocleavage process.