Glass forming donor-substituted s-triazines: Photophysical and electrochemical properties

Triazine derived organic materials possessing various donor-chromophores at the periphery have been designed, synthesized and characterized. The synthesized compounds formed molecular glasses. Their glass transition temperatures ranged from 148 to 235 degrees C. The compounds demonstrated high thermal stability. The onset temperatures of their thermal decomposition exceeded 390 degrees C. The fluorenyl- and carbazolyl-substituted triazine derivatives were shown to be highly fluorescent in solutions and rigid polymer matrices with fluorescence quantum yields being in the range of 0.73-0.82. The phenothiazinyl-substituted triazine derivative showed moderate fluorescence quantum yields in dilute solution (eta = 0.25) or polymer matrix (eta = 0.50). Photophysical studies of phenothiazinyl-substituted triazine derivative in media of different rigidity and polarity revealed its twisted intramolecular charge transfer character. Neat films of the triazine compounds displayed significant fluorescence quenching accompanied by a non-exponential excited-state decay profile which was attributed to migration-assisted exciton quenching at non-radiative decay sites in disordered media. Differential pulse voltammetry studies of the synthesized materials showed that the nature of donor-substituents attached to the triazine core can influence their redox behaviour. Investigation by cyclic voltammetry revealed that the synthesized materials can be used as monomers to prepare high dimensional conjugated polymers by electro-oxidation. Spectroelectrochemical investigation of electro-oxidation products suggested the formation of charged species like polarons or bipolarons. (c) 2013 Elsevier Ltd. All rights reserved.