Highly soluble perylene diimide and oligomeric diimide dyes combining perylene and hexa(ethylene glycol) units: Synthesis, characterization, optical and electrochemical properties

Abstract

A novel, soluble, perylene oligomeric diimide dye, termed EOPPI was synthesized in high yield; for comparison, a small dye molecule, termed EOPDI, was also synthesized; both products readily dissolved in a wide range of organic solvents. The compounds were characterized using NMR, IR, MS, UV–vis, MS, GC–MS, HRMS, DSC, TGA, elemental analysis and cyclic voltammetry. The average molecular mass of EOPPI was 4460, its intrinsic viscosity was 0.3 dl g −1 in m-cresol at 20 °C. The band gap energy ( E g), LUMO and HOMO energy values were 2.25, −3.78 and −6.03 eV for the small dye molecule and 2.24, −3.85 and −6.09 eV for the oligomer, respectively. The temperatures at which the monomer and oligomer began to lose mass were 300 and 375 °C, respectively. The oligomer showed concentration-dependent color tunability.