Molecular dipole-induced photoredox catalysis for hydrogen evolution over self-assembled naphthalimide nanoribbons

Huan Lin, Junhui Wang, Yan Zhuang, Bingqian Liu, Yujiao Zhu, Huaping Jia, Kaifeng Wu, Jinni Shen, Xianzhi Fu, Xuming Zhang (Corresponding Author), Jinlin Long (Corresponding Author)

Research output: Journal article publicationJournal articleAcademic researchpeer-review

35 Citations (Scopus)


D-π-A type 4-((9-phenylcarbazol-3-yl)ethynyl)-N-dodecyl-1,8-naphthalimide (CZNI) with a large dipole moment of 8.49 D and A-π-A type bis[(4,4′-1,8-naphthalimide)-N-dodecyl]ethyne (NINI) with a negligible dipole moment of 0.28 D, were smartly designed and synthesized to demonstrate the evidence of a molecular dipole as the dominant mechanism for controlling charge separation of organic semiconductors. In aqueous solution, these two novel naphthalimides can self-assemble to form nanoribbons (NRs) that present significantly different traces of exciton dissociation dynamics. Upon photoexcitation of NINI-NRs, no charge-separated excitons (CSEs) are formed due to the large exciton binding energy, accordingly there is no hydrogen evolution. On the contrary, in the photoexcited CZNI-NRs, the initial bound Frenkel excitons are dissociated to long-lived CSEs after undergoing ultrafast charge transfer within ca. 1.25 ps and charge separation within less than 5.0 ps. Finally, these free electrons were injected into Pt co-catalysts for reducing protons to H 2 at a rate of ca. 417 μmol h −1 g −1, correspondingly an apparent quantum efficiency of ca. 1.3 % can be achieved at 400 nm.

Original languageEnglish
Article numbere202117645
Number of pages7
JournalAngewandte Chemie International Edition in English
Issue number12
Publication statusPublished - 14 Mar 2022


  • Hydrogen Evolution
  • Molecular Dipole
  • Naphthalimide
  • Photocatalysis
  • Self-Assembly

ASJC Scopus subject areas

  • General Chemistry
  • Catalysis


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