Double hydrogen bonding-induced compact H-type π-π stacking enhancing rapid carrier transfer in perylene diimide supramolecules achieving high oxygen evolution performance

Shulin Meng; Yinan Hu; Haocheng Zhao; Huiting Yao; Yuling Wu; Jinbo Xue; Qianqian Shen

doi:10.1016/j.jcis.2024.04.030

Double hydrogen bonding-induced compact H-type π-π stacking enhancing rapid carrier transfer in perylene diimide supramolecules achieving high oxygen evolution performance

J Colloid Interface Sci. 2024 Jul 15:666:201-209. doi: 10.1016/j.jcis.2024.04.030. Epub 2024 Apr 4.

Authors

Shulin Meng¹, Yinan Hu¹, Haocheng Zhao², Huiting Yao¹, Yuling Wu³, Jinbo Xue⁴, Qianqian Shen⁵

Affiliations

¹ College of Materials Science and Engineering, Taiyuan University of Technology, Taiyuan 030024, China; Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024, China.
² Department of Mechanical and Electrical Engineering, Shanxi Institute of Energy, Jinzhong 030600, China.
³ College of Materials Science and Engineering, Taiyuan University of Technology, Taiyuan 030024, China; Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024, China. Electronic address: wuyuling@tyut.edu.cn.
⁴ Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024, China.
⁵ Key Laboratory of Interface Science and Engineering in Advanced Materials, Taiyuan University of Technology, Taiyuan 030024, China. Electronic address: shenqianqian@tyut.edu.cn.

PMID: 38593654
DOI: 10.1016/j.jcis.2024.04.030

Abstract

Perylene diimides (PDI) are widely used in photocatalytic oxygen evolution due to their deep valence band potentials. Here, we report the synthesis of a unique supramolecular photocatalyst (designated s-PDI-P1) by introducing hydroxyl and carboxyl groups at the imide position of PDI. This modification allows the formation of intermolecular double hydrogen bond structures between the hydroxyl groups, oxygen atoms on the perylene cores and the carboxyl groups. The resulting double hydrogen bonding structures reduce lateral slip and promote the formation of supramolecular structures with H-type π-π stacking. In addition, the intermolecular hydrogen bonding interactions between the hydroxyl groups and the oxygen atoms on the perylene cores bring the PDI molecules closer together, enhancing the conjugation of the PDI supramolecules and facilitating the formation of ultrathin nanosheet-like structures. In this study, we successfully constructed ultrathin nanosheets of the supramolecular photocatalyst s-PDI-P1 with a compact H-type π-π stacking structure, which exhibited enhanced charge transfer capability, shorter charge migration distance, and achieved a high photocatalytic oxygen evolution rate of 3.23 mmolg^-1h^-1. These results highlight the potential of intermolecular double hydrogen bond structures to improve the separation and migration driving force of photogenerated charges, thus providing a novel design strategy for organic photocatalysts.

Keywords: Double hydrogen bond; H-type π-π stacking; Oxygen evolution; PDI; Photocatalyst.