Issue 30, 2024

Molecular “backbone surgery” of electron-deficient heteroarenes based on dithienopyrrolobenzothiadiazole: conformation-dependent crystal structures and charge transport properties

Abstract

Electron-deficient heteroarenes based on dithienopyrrolobenzothiadiazole (BTP) have been highly attractive due to their fascinating packing structures, broad absorption profiles, and promising applications in non-fullerene organic solar cells. However, the control of their crystal structures for superior charge transport still faces big challenges. Herein, a conformation engineering strategy is proposed to rationally manipulate the single crystal structure of BTP-series heteroarenes. The parent molecule BTPO-c has a 3D network crystal structure, which originates from its banana-shaped conformation. Subtracting one thiophene moiety from the central backbone leads to a looser brickwork crystal structure of the derivative BTPO-z because of its interrupted angular-shaped conformation. Further subtracting two thiophene moieties results in the derivative BTPO-l with a compact 2D-brickwork crystal structure due to its quasi-linear conformation with a unique dimer packing structure and short π–π stacking distance (3.30 Å). Further investigation of charge-transport properties via single-crystal organic transistors demonstrates that the compact 2D-brickwork crystal structure of BTPO-l leads to an excellent electron mobility of 3.5 cm2 V−1 s−1, much higher than that of BTPO-c with a 3D network (1.9 cm2 V−1 s−1) and BTPO-z with a looser brickwork structure (0.6 cm2 V−1 s−1). Notably, this study presents, for the first time, an elegant demonstration of the tunable single crystal structures of electron-deficient heteroarenes for efficient organic electronics.

Graphical abstract: Molecular “backbone surgery” of electron-deficient heteroarenes based on dithienopyrrolobenzothiadiazole: conformation-dependent crystal structures and charge transport properties

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Apr 2024
Accepted
18 Jun 2024
First published
18 Jun 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 11761-11774

Molecular “backbone surgery” of electron-deficient heteroarenes based on dithienopyrrolobenzothiadiazole: conformation-dependent crystal structures and charge transport properties

Y. Chen, Z. Wu, Z. Chen, S. Zhang, W. Li, Y. Zhao, Y. Wang and Y. Liu, Chem. Sci., 2024, 15, 11761 DOI: 10.1039/D4SC02794A

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