Synthesis and Photo-Physical Characteristics of ESIPT Inspired 2-Substituted Benzimidazole, Benzoxazole and Benzothiazole Fluorescent Derivatives

• DOI: 10.1007/s10895-011-0962-8
• Publication Date: 2011-09-28T01:34:32Z
• Authors: Vikas S. Padalkar; Abhinav Tathe; Vinod D. Gupta; Vikas S. Patil; Kiran Phatangare; N. Sekar
• Keywords: Models, Molecular; Benzoxazoles; Viscosity; Molecular Conformation; Temperature; Hydrogen Bonding; 01 natural sciences; Absorption; 3. Good health; 0104 chemical sciences; Solvents; Quantum Theory; Benzimidazoles; Benzothiazoles; Fluorescent Dyes

Novel 2-(1H-benzimidazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzoxazol-2-yl)-5-(N,N-diethylamino) phenol, 2-(1,3-benzothiazol-2-yl)-5-(N,N-diethylamino) phenol and their derivatives have been synthesized from p-N,N-diethyl amino salicylaldehyde with different substituted o-phenylenediamine or o-aminophenol or o-aminothiophenol and their photo-physical properties were studied. Effects of solvent polarity in the absorption-emission properties of synthesized compounds were investigated. All these compounds shows excited state intra-molecular proton transfer pathway having single absorption and dual emission characteristics. The fluorescent compounds were characterised by FT-IR, (1)HNMR, (13)C NMR and Mass spectral analysis. TGA analysis showed these compounds are thermally stable up to 200 °C.