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A new spirofluorene-based nonplanar PBI-dyad and its utilization in the film-based photo-production of singlet oxygen

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Abstract

Traditional photosensitizers are predominantly based on various types of polypyrrole macrocycles, which are generally used in homogeneous and/or suspension states. In the present study, a new non-polypyrrole-based photosensitizer (LW-PBI) was developed via the introduction of a nonplanar spirofluorene into a derivative of perylene bisimides (PBI) containing two longalkyl chains. Photophysical studies demonstrated that the compound shows good solubility in common organic solvents, great photochemical stability, and high absorption efficiency in the visible light region. Due to containing of two energetically matchable, independent fluorescent units, the compound as prepared displays strong tendency to form non-fluorescent charge-separated states under light irradiation in polar solvents. Based on the merits, LW-PBI was examined for its catalytic property in the photo-production of singlet oxygen in film state. Luckily, the compound is an effective photosensitizer in the generation of the active oxygen species as verified by its unique reaction with uric acid (UA). Further studies revealed that the effective photo-production of singlet oxygen can be also realized via the utilization of a tiny and low-price LED lamp as a light source and as a film support. Detailed studies on the application of the conceptual device as a medical instrument for photodynamic therapy (PDT) are in progress.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21527802, 2167313, 21820102005), 111 Project (B14041), Program for Changjiang Scholars and Innovative Research Team in University (IRT-14R33).

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Authors and Affiliations

  1. Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, China

    Wenjun Xu, Yanyu Qi, Zhaolong Wang, Gang Wang & Yu Fang

  2. Frontier Institute of Science and Technology, Xi’an Key Laboratory of Sustainable Energy Materials Chemistry, Xi’an Jiaotong University, Xi’an, 710054, China

    Kun Zhou & Gang He

Authors
  1. Wenjun Xu
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  2. Yanyu Qi
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  3. Kun Zhou
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  4. Zhaolong Wang
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  5. Gang Wang
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  6. Gang He
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  7. Yu Fang
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Correspondence to Yu Fang.

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Xu, W., Qi, Y., Zhou, K. et al. A new spirofluorene-based nonplanar PBI-dyad and its utilization in the film-based photo-production of singlet oxygen. Sci. China Chem. 63, 526–533 (2020). https://doi.org/10.1007/s11426-019-9676-y

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