Synthesis, photophysical and electropolymerization properties of thiophene-substituted 2,3-diphenylbuta-1,3-dienes

Maxime Roger (1) , Kassem Amro (2) , Joëlle Rault-Berthelot (3) , Mathias Quiot , Arie van Der Lee (4) , Cyril Poriel , Sébastien Richeter (2) , Sébastien Clément (2) , Philippe Gerbier (2)

1 CETHIL - Centre d'Energétique et de Thermique de Lyon
2 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier
3 ISCR - Institut des Sciences Chimiques de Rennes
4 IEM - Institut Européen des membranes

A series of 2,3-diphenylbuta-1,3-dienes (DPBs) bearing thiophene (T-DPB), bithiophene (BT-DPB) and ethylenedioxythiophene (EDOT-DPB) electropolymerizable units were prepared through desilylation reactions of the corresponding 3,4-diphenylsiloles derivatives. These DPBs derivatives exhibit remarkable different aggregation induced emission (AIE) or aggregation enhanced emission (AEE) behaviour depending on the strength of the molecular interactions occuring in the solid state. Indeed, T-DPB and EDOT-DPB were found to be good AIEgens while BT-DPB exhibited AEE behaviour. Finally, the electrochemical properties of these new materials were investigated revealing for all DPBs the occurrence of electropolymerization processes leading potentially to low band gap polymers.

Domains: Chemical Sciences

Maxime Roger, Kassem Amro, Joëlle Rault-Berthelot, Mathias Quiot, Arie van Der Lee, et al.. Synthesis, photophysical and electropolymerization properties of thiophene-substituted 2,3-diphenylbuta-1,3-dienes. New Journal of Chemistry, 2020, 44 (29), pp.12556-12567. ⟨10.1039/d0nj02382e⟩. ⟨hal-03002432⟩