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In Situ Electrochemical Investigations of Inherently Chiral 2,2′‐Biindole Architectures with Oligothiophene Terminals
Author(s) -
Malacrida Claudia,
Scapinello Luca,
Cirilli Roberto,
Grecchi Sara,
Pei Andrea,
Benincori Tiziana,
Ludwigs Sabine
Publication year - 2021
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.202100511
Subject(s) - electrochromism , monomer , cyclic voltammetry , electrochemistry , thiophene , ferrocene , enantioselective synthesis , amine gas treating , in situ , materials science , conductance , characterization (materials science) , polymer chemistry , combinatorial chemistry , chemistry , electrode , organic chemistry , nanotechnology , polymer , catalysis , mathematics , combinatorics
The synthesis and characterization of three new inherently chiral N , N′ ‐dipropyl‐3,3′‐diheteroaryl‐2,2′‐biindole monomers, nicknamed Ind 2 T 4 , Ind 2 T 6 and Ind 2 Ph 2 T 4 , which differ in the number of thiophenes as terminals, are reported. In addition to a full monomer characterization, stable electroactive oligomeric films were obtained by electro‐oxidation upon cycling to potentials which activate the thiophene terminals. Cyclic voltammetry, UV‐Vis‐NIR spectroelectrochemistry and in situ conductance measurements show that oligomeric films of Ind 2 T 6 present the best stability and electrochromic switching performance. Enantioselective tests with a chiral ferrocene amine clearly show the potential as chiral selectors for analytical and sensing purposes.