A novel conjugated pyrene-bodipy dyad: Synthesis, characterization and properties

Abstract

In the present work, a novel highly conjugated pyrene-boron dipyrromethene (Py-BODIPY) 4 with a donor-acceptor (D-A) skeleton small molecule was synthesized by Sonogashira cross-coupling reaction between 1-ethynylpyrene (2) as a donor group and BODIPY 3 as an acceptor group. The new compound was characterized by fourier transform-infrared (FT-IR), nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MALDI-TOF) and elemental analysis. The photophysical and electrochemical properties of the compound 4 were investigated by UV-vis absorption, fluorescence emission spectroscopy, and cyclic voltammetry (CV) in dichloromethane. It was found from the optical and electrochemical measurements that the target compound has highest occupied molecular orbital energy level (E<inf>HOMO</inf>) at-5.70 eV, lowest unoccupied molecular orbital energy level (E<inf>LUMO</inf>) at-3.27 eV, and the band gap was calculated as 2.43 eV. In addition, theoretical computational studies was also carried out via density functional theory (DFT) for investigation of molecular structure and energy levels of the compound. On the basis of these results, the novel Pyrene-BODIPY compound 4 could be potential candidate for organic light emitting diodes (OLEDs). © 2021 Elsevier B.V., All rights reserved.