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Electron-Withdrawing Substituted Quinazoline Push-Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second-Order Nonlinear Optical Properties
Authors: Moshkina Tatiana N | Le Poul Pascal | Barsella Alberto | Pytela Oldřich | Bureš Filip | Robin-Le Guen Francoise | Achelle Sylvain | Nosova Emiliya V | Lipunova Galina N | Charushin Valery N
Year: 2020
Type of publication: článek v odborném periodiku
Name of source: European Journal of Organic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 5445-5454
Titles:
Language Name Abstract Keywords
cze Chinazolinové push-pull chromofory substituované elektronakceptory: syntéza, elektrochemické, foto fyzikální a nelineární optické vlastnosti Byly syntetizovány chromofory 4‐kyanchinazolin, 2‐(4‐kyanfenyl)chinazolin and 2‐(4‐trifluorfenyl)chinazolin nesoucí elektrondonorní jednotku 5‐(4‐aminofenyl)thiofen‐2‐yl nebo 4‐aminofenyl. Byla provedena UV/Vis a emisní spektroskopie, cyklická voltametrie, metoda EISH a byly provedeny kvantově-chemické výpočty. chinazolin; push-pull deriváty; intramolekulární přenos náboje; nelineární chromofory; fluorescence
eng Electron-Withdrawing Substituted Quinazoline Push-Pull Chromophores: Synthesis, Electrochemical, Photophysical and Second-Order Nonlinear Optical Properties A series of chromophores bearing 4-cyanoquinazoline, 2-(4-cyanophenyl)quinazoline or 2-(4-trifluorophenyl)quinazoline electron-acceptor (A) and 5-(4-aminophenyl)thiophen-2-yl or 4-aminophenyl electron-donor (D) units has been designed. The influence of the electron-withdrawing substituent on the pyrimidine core as well as the nature of the amino electron donating group has been studied by cyclic voltammetry, UV/Vis and emission spectroscopy. Whereas 2-(4-cyanophenyl)quinazoline and 2-(4-trifluorophenyl)quinazoline derivatives are highly luminescent in chloroform solution, 4-cyanoquinazolines are poorly emissive. Interestingly all compounds are luminescent in the solid state with the emission ranging from blue to red. The second order nonlinear optical properties were studied using electric field induced second harmonic generation (EFISH) method. Quantum-chemical calculations corroborate the aforementioned experimental results. Quinazoline; Push-pull derivatives; Intramolecular charge transfer; Nonlinear chromophores; Fluorescence

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