Tripodal molecules with triphenylamine core, diazine peripheral groups and extended π-conjugated linkers. (January 2016)

• Record Type: Journal Article
• Authors: Cvejn, Daniel; Achelle, Sylvain; Pytela, Oldřich; Malval, Jean-Pierre; Spangenberg, Arnaud; Cabon, Nolwenn; Bureš, Filip; Robin-le Guen, Françoise
• Is Part Of: Dyes and pigments. Volume 124(2016)
• Page Start: 101
• Page End: 109
• Publication Date: 2016-01
• Subjects: Diazines -- Triphenylamines -- Nonlinear optics -- Fluorescence -- Intramolecular charge transfer -- Two -photon absorption; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2015.09.012
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: 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 (2 PA) 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. Graphical abstract: Highlights: Octupolar molecules with central triphenylamine and peripheral diazine were prepared. A strong positive emission solvatochromism is observed. These materials exhibit two-photon absorption properties.