Tripodal molecules with triphenylamine core, diazine peripheral groups and extended π-conjugated linkers

Daniel Cvejn (1, 2) , Sylvain Achelle (1) , Oldřich Pytela (2) , Jean-Pierre Malval (3) , Arnaud Spangenberg (3) , Nolwenn Cabon (1) , Filip Bureš (2) , Françoise Robin-Le Guen (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 Institute of Organic Chemistry and Technology [University of Pardubice]
3 IS2M - Institut de Science des Matériaux de Mulhouse

A series of five octupolar molecules with central triphenylamine donor and peripheral diazine electron-withdrawing groups has been prepared. These structures possess extended π-spacer comprising multiple bonds in a combination with 1,4-phenylene and 2,5-thienylene subunits. Starting from tris(4-ethynylphenyl)amine, the key step in the preparation of the chromophores involves triple Sonogashira cross-coupling reaction. The photophysical properties of the compounds are described. A strong positive emission solvatochromism, typical for dyes featuring Intramolecular Charge Transfer (ICT), is observed, two-photon absorption (2PA) properties were also measured. Linear and nonlinear optical properties as well as electronic properties measured by cyclic voltametry and supported by DFT calculation were used to elucidate structure-property relationships

Mots clés: Nonlinear Optics; Triphenylamines; Intramolecular charge transfer; Fluorescence; Diazines

Domaines: Chimie; Matériaux

Daniel Cvejn, Sylvain Achelle, Oldřich Pytela, Jean-Pierre Malval, Arnaud Spangenberg, et al.. Tripodal molecules with triphenylamine core, diazine peripheral groups and extended π-conjugated linkers. Dyes and Pigments, 2016, 124, pp.101-109. ⟨10.1016/j.dyepig.2015.09.012⟩. ⟨hal-01205442⟩