Base Promoted Synthesis of 2-((5-methoxynaphthalen-1-yl)methyl)-3-methyl-5-sec-amino-[1,1′-biphenyl]-4-carbonitrilederivatives: Photophysical, Solvatochromic and DFT studies

Abstract

Newer, simple and efficient synthesis of 2-((5-methoxynaphthalen-1-yl)methyl)-3-methyl-5-sec-amino-[1,1′-biphenyl]-4-carbonitrile derivatives using ring transformation strategy. The synthesized products were characterized by spectral analysis, fluorescence emission and absorption measurements were studied in various solvents having varying polarity and dielectric constants to find out a change in dipole moment in ground state and excited state of derivatives. Lippert–Mataga plots were utilized to know the effect of solvent polarity on spectral behavior of molecules. The position of the Stokes shifts was found to be depends on specific solute–solvent interactions, playing a vital role in electronic excitation of molecules. A rational relationship is examined between fluorescence quantum efficiencies and calculated HOMO and LUMO energies by DFT calculations. The electrochemical investigation of derivatives was performed by cyclic voltammetry.