Strong resonance interaction in 4-{4-[2-(3-dicyanomethylene-5,5-dimethyl-cyclohex-1-enyl)-vinyl]-phenoxy}-butyric acid: Structural, electrochemistry and spectroscopic properties complemented by Natural Bond Orbital and Hirshfeld surface analysis

Abstract

The present investigation deals with the synthesis and characterization of (E)-4-(4-(2-(3-(dicyanomethylene)-5,5-dimethylcyclohex-1-en-1-yl)vinyl)phenoxy)butanoic acid (SLN-01) and its electrochemical and structural study. The compound SLN-01, has been characterized by UV, FTIR, and multinuclear (1H and 13C) NMR spectroscopic studies. DFT calculations were used to estimate redox potential and band gap energies of SLN-01. It's molecular and crystal structures were determined by single-crystal X-ray analysis. The compound (E)-4-(4-(2-(3-(Dicyanomethylene)-5,5-dimethylcyclohex-1-en-1-yl)vinyl)phenoxy) butanoic acid (SLN-01) was crystallized in the triclinic geometry. The Hirshfeld surface analysis was conducted to confirm the supramolecular association formed by the individual conformers and overall packing in the crystal. Natural Bond Orbital population analysis was performed to understand the electronic interactions between the donor and acceptor moieties in the molecule. The targeted compound exhibited a strong absorption at 416 nm (ε= 67,762 ± 4600 L mol−1 cm−1) with emission (λem) at 575 nm (at excitation wavelength λex= 430 nm).