Issue 4, 2024

Backbone-shape engineering of fused-ring electron-deficient molecular semiconductors for unipolar n-type organic transistors: synthesis, conformation changes, and structure–property correlations

Abstract

Backbone-shape engineering is one important strategy towards high-mobility molecular semiconductors. However, it has been seldom employed in modifying fused-ring electron-deficient small molecules, which can provide useful molecular structure–property correlations for developing high-performance n-type organic semiconductors. In this work, we design and synthesize a series of n-type fused-ring small molecules based on ladder-type dithienothiophen-pyrrolobenzothiadiazole (TPBT) derivatives, namely BTPOCl-c, BTPOCl-s, and BTPOCl-w. Due to the different backbone symmetry and length of TPBT derivatives, the above molecules demonstrate three shapes, i.e. C-, S-, and W-backbone shape. Intriguingly, all molecules show a slightly helical conformation between the central cores and end-groups. However, the dihedral angles in the helical conformation are different, which gradually become smaller in the trend of BTPOCl-c < BTPOCl-s < BTPOCl-w. Therefore, changing the backbone shape from C to S and then to W is conducive to enhancing the backbone planarity. Consequently, BTPOCl-w-based unipolar n-type organic transistors display the highest electron mobility among the three molecules. The above result is reasonably explained by BTPOCl-w's deepest energy levels, highest crystallinity with the shortest π–π stacking distance, and larger grain size with fewer grain boundaries. We believe that backbone-shape engineering is a promising approach for developing advanced n-type molecular semiconductors.

Graphical abstract: Backbone-shape engineering of fused-ring electron-deficient molecular semiconductors for unipolar n-type organic transistors: synthesis, conformation changes, and structure–property correlations

Supplementary files

Article information

Article type
Research Article
Submitted
09 nov 2023
Accepted
15 dez 2023
First published
15 dez 2023

Mater. Chem. Front., 2024,8, 1101-1111

Backbone-shape engineering of fused-ring electron-deficient molecular semiconductors for unipolar n-type organic transistors: synthesis, conformation changes, and structure–property correlations

Z. Chen, Z. Wu, Y. Chen, S. Zhang, Z. Jiang, W. Li, Y. Zhao, Y. Wang and Y. Liu, Mater. Chem. Front., 2024, 8, 1101 DOI: 10.1039/D3QM01189E

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