Direct Arylation: A Greener Synthesis of Anthraquinone-Naphthalene diimide-Based Small Chromophores for Applications in Organic Thin Film Transistors

Abstract

In this paper, we report the design and synthesis of three naphthalene diimide- (NDI) and anthraquinone- (AQ) based organic chromophores derived from direct arylation reactions; NDI-AQ, AQ-NDI-AQ and NDI-AQ-NDI. Compared to classic cross-coupling reactions, this method reduced the number of synthetic and purification steps. The chemical structures, photophysical and electrochemical properties of these molecules were characterized using UV-vis spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry (CV). The optoelectronic properties of the three dyes enabled the fabrication of organic thin film transistors (OTFTs). The fabricated OTFTs displayed good n-type semiconducting properties, with electron mobilities ( ${\mu }_e$ ) of 1.5-4.2×10^-4 cm² V^-1 s^-1 .

Keywords: OTFT; anthraquinone; direct arylation; n-type semiconductors; naphthalene diimide.