Premium
Triphenylamino α‐Cyanovinyl‐ and Cyanoaryl‐Based Fluorophores: Solvatochromism, Aggregation‐Induced Emission and Electrochemical Properties
Author(s) -
Balasaravanan Rajendiran,
Sadhasivam Velu,
Sivaraman Gandhi,
Siva Ayyanar
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500488
Subject(s) - triphenylamine , chemistry , solvatochromism , photochemistry , intramolecular force , absorption (acoustics) , electron donor , polar effect , molecule , fluorescence , organic chemistry , physics , quantum mechanics , acoustics , catalysis
A series of linear, V‐shaped and branched triphenylamine/tris(biphenyl)amine‐based derivatives with electron‐withdrawing cyanovinyl‐ and phenyl‐substituted conjugated branches containing either electron‐donating OMe or electron‐withdrawing CN end groups have been synthesized. UV/vis absorption and fluorescence emission data illustrates that introduction of the electron‐donor/acceptor groups induces intramolecular charge transfer that leads to a shift of the absorption onset toward longer wavelengths. Addition of large amounts of water to solutions of triphenylamine derivative caused their emission to reach maximal intensity—these molecules all undergo aggregation‐induced emission; this was confirmed by aggregation studies. All the compounds in this study present a reversible first oxidation process, the potential of which increases with the number of electron‐withdrawing groups in the molecules, as was confirmed by cyclic voltammetry. Furthermore, the influence of solvent polarity on the photophysical properties was investigated. All the triphenylamine derivatives exhibit intensive intramolecular charge‐transfer interactions, giving rise to a substantial extension of their absorption spectral response, which might be potentially used in efficient organic solar cells.