Amino-substituted-1,1-dicyano-2,4-diaryl-1,3-butadiene chromophores: Synthesis and photophysical properties

Mohamed Yahya (1) , Nurgül Seferoğlu (1) , Alberto Barsella (2) , Sylvain Achelle (3) , Zeynel Seferoğlu (1)

1 Gazi University
2 IPCMS - Institut de Physique et Chimie des Matériaux de Strasbourg
3 ISCR - Institut des Sciences Chimiques de Rennes

A series of D-π-A chromophores based on allylidenemalononitrile electron-withdrawing group was designed. The influence of the amino-electron-donating group on the photophysical properties was studied. These compounds, highly thermally stable, exhibit orange-red emission in solution and in solid state. The experimental results have been rationalized by theoretical DFT calculations. The second order nonlinear optical properties were also studied using the electric field induced second harmonic generation (EFISH) method.

Keywords: Allylidenemalononitrile; Intramolecular charge transfer (ICT); DFT calculations; NIR emission; Push–pull; Triphenylamine

Domains: Chemical Sciences; Organic chemistry

Mohamed Yahya, Nurgül Seferoğlu, Alberto Barsella, Sylvain Achelle, Zeynel Seferoğlu. Amino-substituted-1,1-dicyano-2,4-diaryl-1,3-butadiene chromophores: Synthesis and photophysical properties. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy [1994-..], 2021, 248, pp.119178. ⟨10.1016/j.saa.2020.119178⟩. ⟨hal-03038038⟩