Synthesis and Optoelectrical Characterization of Novel Squaraine Dyes Derived from Benzothiophene and Benzofuran.

Abstract

Synthesis and photophysical characterizations of two novel small molecules SQ-BEN-THI and SQ-BEN-FUR with D–A–D molecular structure consisting of squaraine as central unit and benzothiophene and benzofuran as end groups are being reported. Apart from very sharp and intense light absorption by these molecular sensitizers in near-infrared (NIR) wavelength region, their possibility as small molecular organic semiconductor was also explored after fabricating organic field-effect transistors (OFETs). Results obtained from photophysical, electrochemical, and quantum chemical studies were combined to elucidate the structural and optoelectronic properties. Electrical characterization pertaining to the charge-transport properties carried after OFET fabrication exhibited field-effect mobilities of 4.0 × 10–5 and 5.4 × 10–5 cm2/(V s) for SQ-BEN-THI and SQ-BEN-FUR, respectively. After thermal annealing at 130 °C, the field-effect mobility was found to increase for both squaraine dyes. Relatively facile carrier transport in SQ-BEN-FUR compared to that of SQ-BEN-THI could be attributed to relatively higher backbone planarity as indicated from optimized molecular structure obtained after density functional theory calculations. This work may guide for further molecular design and synthesis of novel squaraine dyes for high-performance OFET applications.