Triplet sensitization enables bidirectional isomerization of diazocine with 130 nm redshift in excitation wavelengths.

Autor: Isokuortti J; Faculty of Engineering and Natural Sciences, Tampere University FI-33101 Tampere Finland nikita.durandin@tuni.fi., Griebenow T; Otto-Diels-Institute of Organic Chemistry, Christian-Albrechts-University of Kiel 24098 Kiel Germany rherges@oc.uni-kiel.de., von Glasenapp JS; Otto-Diels-Institute of Organic Chemistry, Christian-Albrechts-University of Kiel 24098 Kiel Germany rherges@oc.uni-kiel.de., Raeker T; Institute for Physical Chemistry, Department for Theoretical Chemistry, Christian-Albrechts-University of Kiel 24098 Kiel Germany., Filatov MA; School of Chemical and Pharmaceutical Sciences, Technological University Dublin, City Campus Grangegorman Dublin 7 Ireland., Laaksonen T; Faculty of Engineering and Natural Sciences, Tampere University FI-33101 Tampere Finland nikita.durandin@tuni.fi.; Drug Research Program, Division of Pharmaceutical Biosciences, Faculty of Pharmacy, University of Helsinki Finland., Herges R; Otto-Diels-Institute of Organic Chemistry, Christian-Albrechts-University of Kiel 24098 Kiel Germany rherges@oc.uni-kiel.de., Durandin NA; Faculty of Engineering and Natural Sciences, Tampere University FI-33101 Tampere Finland nikita.durandin@tuni.fi.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2023 Aug 08; Vol. 14 (34), pp. 9161-9166. Date of Electronic Publication: 2023 Aug 08 (Print Publication: 2023).
DOI: 10.1039/d3sc02681g
Abstrakt: Diazocines are bridged azobenzenes with phenyl rings connected by a CH 2 -CH 2 group. Despite this rather small structural difference, diazocine exhibits improved properties over azobenzene as a photoswitch and most importantly, its Z configuration is more stable than the E isomer. Herein, we reveal yet another unique feature of this emerging class of photoswitches. In striking contrast to azobenzenes and other photochromes, diazocine can be selectively switched in E → Z direction and most intriguingly from its thermodynamically stable Z to metastable E isomer upon successive excitation of two different triplet sensitizers present in solution at the same time. This approach leads to extraordinary large redshift of excitation wavelengths to perform isomerization i.e. from 400 nm blue to 530 nm green light ( Z → E ) and from 530 nm green to 740 nm far-red one ( E → Z ), which falls in the near-infrared window in biological tissue. Therefore, this work opens up of potential avenues for utilizing diazocines for example in photopharmacology, smart materials, light energy harvesting/storage devices, and out-of-equilibrium systems.
Competing Interests: There are no conflicts to declare.
(This journal is © The Royal Society of Chemistry.)
Databáze: MEDLINE
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