Control of the optical properties upon a reversible [2+2] cycloaddition of 3-(4-N,N-dibutylamino)-styryl)-3’-(dicyanovinyl)-bithiophene

Hecham Aboubakr (1) , Jean-Marc Sotiropoulos (2) , Hugues Brisset (3) , Jean-Manuel Raimundo (1)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille
2 IPREM - Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux
3 MAPIEM - Laboratoire Matériaux Polymères Interfaces Environnement Marin - EA 4323

In the course of our studies of D-π-A push-pull chromophores we have envisioned the design of the novel 3-(4-N,N-dibutylamino)-styryl)-3’-(dicyanovinyl)-bithiophene derivative as a potential building block for optoelectronic applications. However, during the synthesis of this chromophore, a cycloadduct compound confirmed by X-ray structure was obtained by an intramolecular [2 + 2] cycloaddition reaction. The retro cycloaddition reaction carried out in thermal conditions and followed by UV–Visible absorption spectrophotometry afforded quantitively the target chromophore. Electrochemical properties recorded are in good agreement with open and close compounds. Mechanism involves cis/trans isomerization was proposed to explain the complete conversion

Keywords: Cycloadduct; Optoelectronics; Push-pull chromophore; Thiophene; modelisation

Domains: Chemical Sciences; Material chemistry; Chemical Sciences; Polymers; Chemical Sciences; Theoretical and/or physical chemistry; Chemical Sciences; Analytical chemistry; Chemical Sciences; Organic chemistry

Hecham Aboubakr, Jean-Marc Sotiropoulos, Hugues Brisset, Jean-Manuel Raimundo. Control of the optical properties upon a reversible [2+2] cycloaddition of 3-(4-N,N-dibutylamino)-styryl)-3’-(dicyanovinyl)-bithiophene. Tetrahedron, 2020, 76 (33), pp.131384. ⟨10.1016/j.tet.2020.131384⟩. ⟨hal-02902701⟩