Synthesis, characterization, and theoretical investigation of optical and nonlinear optical (NLO) properties of triazene-based push–pull chromophores


Mammadova F., Ozsinan S., Okutan M., DENGİZ Ç.

Journal of Molecular Structure, vol.1220, 2020 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1220
  • Publication Date: 2020
  • Doi Number: 10.1016/j.molstruc.2020.128726
  • Title of Journal : Journal of Molecular Structure
  • Keywords: Donor-acceptor systems, Nonlinear optics, Charge transfer, Conjugation, Cycloaddition, Solvatochromism, 2+2 CYCLOADDITION-RETROELECTROCYCLIZATION, CHARGE-TRANSFER INTERACTIONS, DONOR-ACCEPTOR CHROMOPHORES, RAY CRYSTAL-STRUCTURES, 7,7,8,8-TETRACYANOQUINODIMETHANE TCNQ, SMALL MOLECULES, SPIRO SYSTEMS, COMPLEXES, RUTHENIUM, CHEMISTRY

Abstract

A short and efficient synthetic strategy for the synthesis of triazene-substituted push-pull dyes has been developed. The formal [2 + 2] cycloaddition-retroelectrocyclization was utilized for the preparation of the target push-pull dyes. These atom-economic, click-type chemical transformations occurred under ambient conditions and provided structurally interesting push-pull dyes in high yields. The effects of different triazene substituents on optical and non-linear optical properties were investigated by means of density functional theory (DFT), in order to support design criteria. The dipole moment, HOMO-LUMO gaps, electronegativity, global chemical hardness and softness, average polarizability, first hyper-polarizability were calculated for push-pull dyes at the CAM-B3LYP/6-31++G(d,p) level of theory. Frontier orbital depictions and electrostatic potential maps were used to establish charge-transfer characteristics of the aforementioned molecules. (C) 2020 Elsevier B.V. All rights reserved.