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Tuning the Redox Properties of Photochromic Diarylethenes by Introducing Electron‐Withdrawing Substituents
Author(s) -
Berberich Martin,
Würthner Frank
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201200179
Subject(s) - photochromism , chemistry , redox , moiety , nitro , cyclic voltammetry , photochemistry , polar effect , electron acceptor , absorption (acoustics) , molecular switch , absorption spectroscopy , acceptor , combinatorial chemistry , stereochemistry , organic chemistry , electrochemistry , molecule , electrode , materials science , alkyl , physics , composite material , quantum mechanics , condensed matter physics
A series of seven photochromic diarylethenes (DAEs) with various electron‐withdrawing substituents and their respective closed‐form isomers (DAE C ) were synthesized and the optical and redox properties of these photochromes were investigated by UV/vis absorption spectroscopy and cyclic voltammetry. Our comparative studies with these DAEs revealed that the absorption properties of the closed forms and the redox potentials of the open and closed isomers appreciably depend on the number and nature of the electron‐withdrawing groups introduced into the DAE unit. The DAE derivatives can be photochemically switched between two different states with different redox properties. Most prominently, photochrome 3 with two nitro groups has a first reduction potential for the open form 3 o of −1.51 V and for the corresponding closed form 3 c of −0.96 V, and, therefore, is particularly interesting as switchable electron‐acceptor moiety in photochromic systems.