The synthesis and characterization of three new inherently chiral N,N′-dipropyl-3,3′-diheteroaryl-2,2′-biindole monomers, nicknamed Ind2T4, Ind2T6 and Ind2Ph2T4, 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 Ind2T6 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.

In Situ Electrochemical Investigations of Inherently Chiral 2,2′-Biindole Architectures with Oligothiophene Terminals

Scapinello L.;Penoni A.;Benincori T.
;
2021-01-01

Abstract

The synthesis and characterization of three new inherently chiral N,N′-dipropyl-3,3′-diheteroaryl-2,2′-biindole monomers, nicknamed Ind2T4, Ind2T6 and Ind2Ph2T4, 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 Ind2T6 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.
2; 2′-biindoles; electroactive films; mixed valence conductivity; oligothiophenes; π spacer
Malacrida, C.; Scapinello, L.; Cirilli, R.; Grecchi, S.; Penoni, A.; Benincori, T.; Ludwigs, S.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2114538
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