Synergistic effects of side-functionalization and aza-substitution on the charge transport and optical properties of perylene-based organic materials: a DFT study. (18th May 2022)

• Record Type: Journal Article
• Authors: Debata, Suryakanti; Khatua, Rudranarayan; Sahu, Sridhar
• Is Part Of: New journal of chemistry. Volume 46:Number 21(2022)
• Page Start: 10402
• Page End: 10414
• Publication Date: 2022-05-18
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/d1nj06084h
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : The physicochemical properties of organic materials are subject to the chemical structure of the molecular unit and the arrangement of molecules in a crystal. Abstract : The physicochemical properties of organic materials are subject to the chemical structure of the molecular unit and the arrangement of molecules in a crystal. Herein, a series of perylene-based small-molecule organic semiconductors (OSCs) have been theoretically designed by subsequent functionalization of cyclic side chains and N-doping in perylene units. Different physicochemical properties of the designed molecules were explored using density functional theory. As a result of the synergistic effects of side-functionalization and aza-substitution in the parent perylene, a low-lying LUMO level (−3.926 eV) and high electron affinity (2.939 eV) have been achieved for the designed compound (P16 ), which are favourable for air-stable electron injection. The molecular packing motif and high intermolecular electron coupling in the P16 crystal led to enhanced electron mobility up to 0.017 cm 2 V −1 s −1, making it a promising air-stable n-channel OSC. In addition, these perylene derivatives are also found to be optically active in the UV-visible region, which further experiences a bathochromic shift after substituting all peri-positions with the cyclic-substituents. The present study is therefore aimed at designing novel n-type and optically active small-molecule OSCs, which will be beneficial for several organic electronic devices.