The effect of the number of conjugated C=C bonds on the ESIPT and ICT reactions of SNCN derivatives.

ABSTRACT

The electronic structure of the molecule is significantly influenced by the number of conjugated C=C bonds. In this work, the influence of the conjugated C=C bonds of the SNCN derivatives on the excited state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) properties are studied by density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculation level is proved to be reasonable by calculating electronic spectra. The hydrogen bond parameters, infrared vibrational frequency (IR), reduction density gradient (RDG) isosurface, topological analysis and potential energy curves of SNCN derivatives in ground state (S0) and the first excited state (S1) are analyzed. According to theoretical research results, ESIPT reaction has a higher likelihood of occurring in the S1 state. Moreover, the ESIPT reaction becomes more challenging to occur with the number of conjugated C=C bonds rising. Finally, the analyses of the frontier molecular orbitals (FMOs), dipole moment and charge transfer transition confirm that the ICT effect is aided by the increased number of conjugated C=C bonds. This work indicates that the number of conjugated C=C bonds can regulate the ESIPT and ICT processes, which provides guidance for the study of fluorescent groups with similar characteristics.