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 witha donor-acceptor (D-A) skeleton small molecule was synthesized by Sonogashira cross-coupling reactionbetween 1-ethynylpyrene (2) as a donor group and BODIPY 3 as an acceptor group. The new compound wascharacterized by fourier transform-infrared (FT-IR), nuclear magnetic resonance spectroscopy (NMR), massspectrometry (MALDI-TOF) and elemental analysis. The photophysical and electrochemical properties of thecompound 4 were investigated by UV-vis absorption, fluorescence emission spectroscopy, and cyclicvoltammetry (CV) in dichloromethane. It was found from the optical and electrochemical measurements thatthe target compound has highest occupied molecular orbital energy level (EHOMO) at -5.70 eV, lowestunoccupied molecular orbital energy level (ELUMO) at -3.27 eV, and the band gap was calculated as 2.43 eV. Inaddition, theoretical computational studies was also carried out via density functional theory (DFT) forinvestigation of molecular structure and energy levels of the compound. On the basis of these results, thenovel Pyrene-BODIPY compound 4 could be potential candidate for organic light emitting diodes (OLEDs).