A Novel Conjugated Pyrene-BODIPY Dyad: Synthesis, Characterization and Properties

Abstract

In the present work, a novel highly conjugated pyrene-BODIPY (BODPhPy) with a D-A (donor-acceptor) skeleton small molecule was synthesized by Sonogashira cross-coupling reaction between 1-ethynylpyrene as a donor group (EthyPy) and BODIPY as an acceptor group (BrPh-BOD). 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 (BODPhPy) were investigated by UV-vis absorption, fluorescence emission spectroscopy, and cyclic voltammetry (CV) in dichloromethane. It was found from the optical and electrocemical measurements that the target compound has highest occupied molecular orbital energy level (EHOMO) of -5.70 eV, lowest unoccupied molecular orbital energy level (ELUMO) of -3.27 eV, and the band gap was calculated as 2.43 eV. In addition, theoretic computational studies was also carried out via density functional techniques (DFT) for investigation of molecular structure and energy levels of the compound. According to this results, the novel compound could be potential candidate for optoelectronic devices.

Keywords

• Pyrene
• BODIPY
• optoelectronic device

References

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