The Influence of the Formal Replacement of Thiophenes by Stannoles in Terthiophene and Sexithiophene on the Optoelectronic Properties and Electrochemical Behavior - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Dalton Transactions Année : 2021

The Influence of the Formal Replacement of Thiophenes by Stannoles in Terthiophene and Sexithiophene on the Optoelectronic Properties and Electrochemical Behavior

Résumé

Polystannoles with thienyl co-monomers are in many ways similar to polythiophenes, but they display much reduced band gaps. However, their polymerization processes are not well researched. Thiophene can be oxidatively electropolymerized, but as stannoles are organometallic, the fundamental question arises whether their inclusion in a conjugated backbone can protect them sufficiently to be able to perform an oxidative electropolymerization. As well-defined oligothiophenes can be used as models to understand the optical and electronic properties of polythiophenes, we transposed this concept on stannole containing polymers; therefore we synthesized a monomeric 1 and dimeric thiophene-flanked stannole 2 and investigated their optoelectronic properties comparatively including polystannoles and the corresponding oligothiophenes in our analysis. With respect to monomer 1, a significantly redshifted absorption (max = 510 nm  = 93 nm) and a small optical band gap (Eg,opt(2) = 2.13 eV), close to the band gap of polymeric stannoles, was observed. In comparison to oligothiophenes, these thienyl-flanked stannoles exhibited a redshift in absorption and emission as well as a lower oxidation potential. Despite these differences, they showed an oligothiophene-like electrochemical behavior. Stannole 1 and the dimer 2 were subjected to an electropolymerization process. This process was investigated in detail by spectroelectrochemical methods which showed that radical cation species were formed in situ but readily decomposed. Nevertheless, under the milder multiscan cyclovoltammetric conditions, electropolymerization occurred as shown by cyclovoltammetry.

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hal-03219553 , version 1 (06-05-2021)

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Jonas Hoffmann, Isabel-Maria Ramirez y Medina, Muriel Hissler, Anne Staubitz. The Influence of the Formal Replacement of Thiophenes by Stannoles in Terthiophene and Sexithiophene on the Optoelectronic Properties and Electrochemical Behavior. Dalton Transactions, 2021, 50 (18), pp.6213-6221. ⟨10.1039/D1DT00565K⟩. ⟨hal-03219553⟩
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