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Precise Manipulation of Excited-State Intramolecular Proton Transfer via Incorporating Charge Transfer toward High-Performance Film-Based Fluorescence Sensing

  • Ke Liu
    Ke Liu
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    More by Ke Liu
  • Jing Zhang
    Jing Zhang
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    More by Jing Zhang
  • Qiyuan Shi
    Qiyuan Shi
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    More by Qiyuan Shi
  • Liping Ding
    Liping Ding
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    More by Liping Ding
  • Taihong Liu*
    Taihong Liu
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    *Email: [email protected]
    More by Taihong Liu
  • , and 
  • Yu Fang*
    Yu Fang
    Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Shaanxi, Xi’an 710062, China
    *Email: [email protected]
    More by Yu Fang
Cite this: J. Am. Chem. Soc. 2023, 145, 13, 7408–7415
Publication Date (Web):March 17, 2023
https://doi.org/10.1021/jacs.2c13843
Copyright © 2023 American Chemical Society

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    Abstract

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    Excited-state intramolecular proton transfer (ESIPT) has been widely employed for the design of a variety of functionality-led molecular systems. However, precise manipulation of the excited-state reaction is challenging. Herein, we report a new tactic for tuning ESIPT via incorporating an excited-state intramolecular charge transfer (ESICT) process. Specifically, three o-carborane derivatives, NaCBO, PaCBO, and PyCBO, were designed, where the 2-(2′-hydroxyphenyl)-benzothiazole is a typical ESIPT unit functioning as an electron acceptor, and the electron-donating units are naphthyl-(Na), phenanthrenyl-(Pa), and pyrenyl-(Py), respectively. The architectures of the molecules are featured with a face-to-face alignment of the two units. Spectroscopy and theoretical calculation studies revealed that the electron-donating capacity of the donors and solvent polarity continuously modulate the ESIPT/ESICT energetics and dynamics, resulting in distinct emissions. Moreover, the molecules depicted not only highly porous structures but also very different fluorescent colors in the solid state, enabling highly selective film-based fluorescence sensing of mustard gas simulant, 2-chloroethyl ethyl sulfide, with a detection limit of 50 ppb and a response time of 5 s. This work thus provides a reliable strategy for the creation of high-performance sensing fluorophores via ESIPT manipulation.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c13843.

    • Experimental section, detailed synthesis procedures, and characterization data of the compounds (PDF)

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    CCDC 2233333, 2233335, and 2233340 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    Cited By

    This article is cited by 7 publications.

    1. Xiaohang Chen, XinYu Zhang, Juan Han, Shu-Hua Xia. Photochemical Mechanisms of Hydroxyquinoline Benzimidazole: Insights from Electronic Structure Calculations and Nonadiabatic Dynamics Simulations. The Journal of Physical Chemistry A 2024, 128 (11) , 1984-1992. https://doi.org/10.1021/acs.jpca.3c07298
    2. Jian-Kai Wang, Chih-Hsing Wang, Chi-Chi Wu, Kai-Hsin Chang, Chun-Hsiang Wang, Yi-Hung Liu, Chao-Tsen Chen, Pi-Tai Chou. Hydrogen-Bonded Thiol Undergoes Unconventional Excited-State Intramolecular Proton-Transfer Reactions. Journal of the American Chemical Society 2024, 146 (5) , 3125-3135. https://doi.org/10.1021/jacs.3c10405
    3. Jingjing Liang, Dingfang Hu, Wenjun Xu, Lingya Peng, Ke Liu, Yu Fang. Interfacially Confined Dynamic Reaction Resulted to Fluorescent Nanofilms Depicting High-Performance Ammonia Sensing. Analytical Chemistry 2024, 96 (5) , 2152-2157. https://doi.org/10.1021/acs.analchem.3c05032
    4. Yulin Zhu, Yuguo Tang, Peng Miao. Intramolecular Charge Transfer of Gold Nanoclusters for pH Indicating. Langmuir 2024, 40 (1) , 1130-1136. https://doi.org/10.1021/acs.langmuir.3c03497
    5. Lu Liu, Sheng Li, Nan Zhang, Qiyuan Shi, Ke Liu, Taihong Liu, Zhiyan Huang, Liping Ding, Yu Fang. Comparative Observation of Distinct Dynamic Stokes Shifts in Diaryl BODIPY Triads with Broadband Two-Photon Absorption. The Journal of Physical Chemistry B 2023, 127 (47) , 10171-10178. https://doi.org/10.1021/acs.jpcb.3c06757
    6. Peng-Yan Fu, Shao-Zhe Yi, Mei Pan, Cheng-Yong Su. Excited-State Intramolecular Proton Transfer (ESIPT) Based Metal–Organic Supramolecular Optical Materials: Energy Transfer Mechanism and Luminescence Regulation Strategy. Accounts of Materials Research 2023, 4 (11) , 939-952. https://doi.org/10.1021/accountsmr.3c00139
    7. Nan Zhang, Lu Liu, Haixia Chang, Ke Liu, Taihong Liu, Liping Ding, Yu Fang. Tunable Non-Kasha Behaviors and Excited-State Dynamics of Quadrupolar Squaraine Aggregates. The Journal of Physical Chemistry Letters 2023, 14 (32) , 7283-7289. https://doi.org/10.1021/acs.jpclett.3c02029

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