Study of modulating opto-electrochemical properties in Suzuki coupled phenazine derivatives for organic electronics

Abstract

In this work, five 3,6,11-trisubstituted-dibenzo[a,c]phenazine (2–6) derivatives were synthesized by employing Palladium-catalyzed Suzuki–Miyaura ‘C–C bond’ coupling reaction and characterized. Absorption spectra of 2–6 show the formation of charge-transfer complexes. Dyes exhibit blue-green fluorescence with emission maxima 434–506 nm in various solvents and neat solid film. To elucidate AIE phenomenon, photophysical properties of dye 2 and 3 in different THF/water mixture were studied. The HOMO and LUMO energy level were found in the range of\u2009−\u20096.38 to\u2009−\u20096.82 eV and\u2009−\u20093.67 to\u2009−\u20093.75 eV with an electrochemical bandgap of 2.71–3.08 eV. The HOMO and LUMO distribution in molecules were further studied by DFT/TD–DFT calculations. Herein, characteristic blue emission, comparable energy levels with n-type materials, and good thermal stability of derivatives make them a potential candidate for their application in optoelectronics.