Synthesis, molecular structure, spectroscopic investigations and computational study of a potential molecular switch of 2-([1,1’-biphenyl]-4-yl)-2-methyl-6-(4-nitrophenyl)-4-phenyl-1,3 diazabicyclo [3.1.0]hex-3-ene

Abstract

This work presents a combined experimental and theoretical study on a photochromic compound, 2-([1,1’-biphenyl]-4-yl)-2-methyl-6-(4-nitrophenyl)-4-phenyl-1,3 diazabicyclo [3.1.0]hex-3-ene, existing in closed form (‘A’) and open form (‘B’). The spectroscopic properties of the title compound have been investigated by using IR, UV–Vis and 1H NMR techniques. The molecular geometry and spectroscopic data of the title compound have been calculated by using the density functional method (B3LYP) invoking 6-311G(d,p) basis set. UV-Vis spectra of the two forms were recorded. The excitation energies, oscillator strength, etc., were calculated by time-dependent density functional theory (TD-DFT). Furthermore, molecular electrostatic potential map (MEP), frontier molecular orbital analysis (HOMO–LUMO), total density of state (TDOS) and reactivity descriptors were found and discussed. We applied a first-principles computational approach to study a light-sensitive molecular switch. We find that the conductance of the two isomers varies dramatically, which suggests that this system has potential use as a molecular switch. A novel photochromic compound was synthesized. The UV–Vis band in "A" form was observed at 310 nm (colorless), and for "B" form at 310 and 415 nm (blue color). The molecule is proposed as a potential photoinduced molecular switch for a molecular electronic device.