Photophysical and Electrochemical Properties of Novel Symmetrical and Unsymmetrical 1,4,5,8-naphthalenetetracarboxydiimide Derivatives

Abstract

A series of symmetrical and unsymmetrical 1,4,5,8-naphthalenetetracarboxydiimide (NDIM) derivatives were characterized by UV-visible and fluorescence spectral analyses in order to understand the relationships between their structures and physical properties. The UV-visible spectral analyses showed the intermolecular interactions on phenyl group of 3,3-diphenylpropyl derivatives, and the fluorescence spectra suggested the weak intermolecular interactions for 2,5-di-tert-butylphenyl derivatives. These results revealed that 3,5-di-tert-butylphenyl group is one of the best substituents for disturbing the intermolecular interaction. The redox potentials of reduction for NDIM derivatives were slightly shifted to the negative region by the introduction of electron-donating substituents.