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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202105852
Subject(s) - electrochromism , redox , chemistry , cationic polymerization , conjugated system , electron transfer , fluorene , electrochemistry , combinatorial chemistry , viologen , molecular switch , electrochromic devices , photochemistry , polymer , polymer chemistry , organic chemistry , molecule , 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.