ISSN : 1226-0517(Print)
ISSN : 2288-9604(Online)
ISSN : 2288-9604(Online)
Journal of Korean Society for Imaging Science and Technology Vol.22 No.2 pp.22-28
DOI : https://doi.org/10.14226/KSIST.2016.22.02.05
DOI : https://doi.org/10.14226/KSIST.2016.22.02.05
Synthesis and Solvatochromic Properties of Quinoxaline Derivative with D-A Structure
Abstract
Quinoxaline derivative (TPAQ) was successfully synthesized via consecutive Heck-coupling and acid-catalyzed dehydration reaction. The strong electron-donating triphenylamine moiety was introduced at both ends of electron-accepting 3,3‘-diaminobenzidine-based quinoxaline central core to afford unique dumbell-like molecular geometry. The optical and electrochemical properties of TPAQ were investigated using UV-visible and cyclovoltammetric analyses. TPAQ exhibits the maximum absoption peaks at 410 and 390 nm in solution and on film, respectively. HOMO and LUMO energy levels of TPAQ are also evaluated by cyclic voltammetry and the values are – 5.03 and 3.24 eV, respectively. In addition, TPAQ shows outstanding solvatochromic properties in various solvents, because the energy level of excited-state with stronger dipole through the facile intramolecular charge transfer process, can be strongly affected by solvent polarities, which is the unique feature of organic conjugated materials with D-A configuration.