In the present paper, the synthesis and characterization of 2,2'-bis{bi[2,2'-(3,4-ethylenedioxy)thiophen-5- yl]}-3,3'-bithianaphthene, nicknamed BT2E4, is reported. We show that electrooligomerization of BT2E4 leads to electroactive films which are evaluated by cyclic voltammetry (CV), UV/vis spectroelectrochemistry and CV coupled with in-situ conductance measurements. Direct comparisons to the properties of the oligomers obtained from the atropisomeric all-thiophene analogue BT2T4 show that the introduction of EDOT leads to a strong reduction of the band-gap, an overall red-shifted absorption spectrum and a rigidification of the structure. Finally, DFT and TD-DFT calculations were performed in parallel to investigate and to compare the electronic and molecular structures of neutral and charged monomer and oligomer species.

Electrochemical studies of a new, low-band gap inherently chiral ethylenedioxythiophene-based oligothiophene

Benincori T.
;
Appoloni, G.;
2018-01-01

Abstract

In the present paper, the synthesis and characterization of 2,2'-bis{bi[2,2'-(3,4-ethylenedioxy)thiophen-5- yl]}-3,3'-bithianaphthene, nicknamed BT2E4, is reported. We show that electrooligomerization of BT2E4 leads to electroactive films which are evaluated by cyclic voltammetry (CV), UV/vis spectroelectrochemistry and CV coupled with in-situ conductance measurements. Direct comparisons to the properties of the oligomers obtained from the atropisomeric all-thiophene analogue BT2T4 show that the introduction of EDOT leads to a strong reduction of the band-gap, an overall red-shifted absorption spectrum and a rigidification of the structure. Finally, DFT and TD-DFT calculations were performed in parallel to investigate and to compare the electronic and molecular structures of neutral and charged monomer and oligomer species.
2018
bisEDOT; Cyclic oligomers; Low-band gap monomer; Mixed valence conductivity; Self-rigidification;
Benincori, T.; Gámez-Valenzuela, S.; Goll, M.; Bruchlos, K.; Malacrida, C.; Arnaboldi, S.; Mussini, P. R.; Panigati, M.; López Navarrete, J. T.; Ruiz ...espandi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2074570
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