Naphthalimide-Fused Dipyrrins: Tunable Halochromic Switches and Photothermal NIR-II Dyes

Yogesh Kumar Maurya, Piotr J. Chmielewski, Joanna Cybińska, Bibek Prajapati, Tadeusz Lis, Seongsoo Kang, Seokwon Lee, Dongho Kim, Marcin Stępień

Research output: Contribution to journalArticlepeer-review


A family of tunable halochromic switches is developed using a naphthalimide-fused dipyrrin as the core π-conjugated motif. Electronic properties of these dipyrrins are tuned by substitution of their alpha and meso positions with aryl groups of variable donor–acceptor strength. The first protonation results in a conformational change that enhances electronic coupling between the dipyrrin chromophore and the meso substituent, leading to halochromic effects that occasionally exceed 200 nm and switch the absorption between the near-infrared (NIR)-I and NIR-II ranges. A NIR-II photothermal effect, switchable by acid–base chemistry is demonstrated for selected dipyrrins. Further protonation is possible for derivatives bearing additional amino groups, leading to up to four halochromic switching step. The most electron-rich dipyrrins are also susceptible to chemical oxidation, yielding NIR-absorbing radical cations and closed-shell dications.

Original languageEnglish
JournalAdvanced Science
Publication statusAccepted/In press - 2022

Bibliographical note

Funding Information:
Financial support from the Foundation for Polish Science (TEAM POIR.04.04.00‐00‐5BF1/17‐00 to M.S.) and the National Science Centre of Poland (UMO‐2018/29/B/ST5/01842 to M.S.) is gratefully acknowledged. Computational work was performed at the Wrocław Center for Supercomputing. The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2021R1A2C3006308).

Publisher Copyright:
© 2022 The Authors. Advanced Science published by Wiley-VCH GmbH.

All Science Journal Classification (ASJC) codes

  • Medicine (miscellaneous)
  • Chemical Engineering(all)
  • Materials Science(all)
  • Biochemistry, Genetics and Molecular Biology (miscellaneous)
  • Engineering(all)
  • Physics and Astronomy(all)


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