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Electrochromic Polycationic Organoboronium Macrocycles with Multiple Redox States
Author(s) -
Shimoyama Daisuke,
BaserKirazli Nurcan,
Lalancette Roger A.,
Jäkle Frieder
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202105852
Subject(s) - electrochromism , redox , chemistry , combinatorial chemistry , nanotechnology , materials science , organic chemistry , electrode
Polycationic macrocycles are attractive as they display unique molecular switching capabilities arising from their redox properties. Although diverse polycationic macrocycles have been developed, those based on cationic boron systems remain very limited. We present herein the development of novel polycationic macrocycles by introducing organoboronium moieties into a conjugated organoboron macrocyclic framework. These macrocycles consist of four bipyridylboronium units that are connected by fluorene and either electron‐deficient arylborane or electron‐rich arylamine moieties. Electrochemical studies reveal that the macrocycles undergo reversible multi‐step redox processes with transfer of up to 10 electrons. Switchable electrochromic behavior is demonstrated via spectroelectrochemical studies and the observed color changes are rationalized by correlation with computed electronic transitions using DFT methods.