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Methylthiolation Modified Bay‐Annulated Indigo Derivatives for Enhanced Performance in Organic Field‐Effect Transistors
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Methylthiolation Modified Bay‐Annulated Indigo Derivatives for Enhanced Performance in Organic Field‐Effect Transistors
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Journal Article
Methylthiolation Modified Bay‐Annulated Indigo Derivatives for Enhanced Performance in Organic Field‐Effect Transistors
2025
Overview
Indigo is one of the most well‐known natural dyes and has attracted significant research interest due to its low cost and exceptional stability. Notably, bay‐annulated indigo (BAI) has been reported as an effective electron acceptor and is widely used in various applications. Herein, a methylthio‐substituted BAI derivative, compound 1, is successfully synthesized and the impact of methylthio substitution on its optoelectronic properties is investigated. UV–vis absorption and fluorescence spectra reveal that compound 1 displays a significant redshift compared to the nonmethylthio‐substituted compound 2. Cyclic voltammetry measurements and density functional theory calculations indicate that compound 1 has a narrower highest occupied molecular orbital and lowest unoccupied molecular orbital gap, demonstrating the prominent influence of methylthio side chains in modulating molecular electronic properties. Importantly, the organic field‐effect transistor device based on compound 1 exhibits a hole mobility 3.5 times higher than that of the nonmethylthio‐substituted compound 2. Furthermore, atomic force microscopy characterization reveals the formation of needle‐like crystallites in the compound 1 film after annealing, whereas compound 2 forms an amorphous thin film. These results suggest that methylthiolation is an effective strategy for tuning intermolecular interactions in novel BAI derivatives, and compound 1 is a promising hole‐transporting material. A methylthio‐substituted bay‐annulated indigo (BAI) derivative (compound 1) with enhanced optoelectronic properties is synthesized. Compared to nonmethylthio‐substituted compound 2, compound 1 exhibits a redshifted absorption and 3.5‐fold higher hole mobility in organic field‐effect transistors. These results demonstrate that methylthiolation effectively tunes intermolecular interactions and electronic properties, making compound 1 a promising hole‐transporting material for organic electronics.
