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Orthogonal carbazole-perylene bisimide pentad:a photoconversion-tunable photosensitizer with diversified excitation and excited-state relaxation pathways

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Science China Chemistry 2021年第12期64卷 2193-2202页

作者： Zhaolong Wang Yue Sun Simin Lin Gang Wang Xingmao Chang Xinyu Gou Taihong Liu Shengye Jin Gang He Yu-Chen Wei Pi-Tai Chou Yu Fang Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education School of Chemistry and Chemical EngineeringShaanxi Normal UniversityXi’an710119China College of Life Sciences Shaanxi Normal UniversityXi’an710119China State Key Laboratory of Molecular Reaction Dynamics and Collaborative Innovation Center of Chemistry for Energy Materials(iChEM) Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China Frontier Institute of Science and Technology Xi’an Jiaotong UniversityXi’an710054China Department of Chemistry Taiwan UniversityTaipei10617China

Integrating multiple photosensitive properties into an“all-in-one”photosensitizer(PS)shows great promise for the treatment of cancers owing to synergistic effect among them.However,the development of such PSs,especially those that need a single laser source,remains a challenge.Herein,we report an orchestration of electron donors and acceptors in a propeller-like pentad,PBI-4Cz,where four carbazole(Cz)units are covalently linked to the ortho-positions of the perylene bisimide(PBI)core.Strong intramolecular donor-acceptor interaction significantly quenches the luminescence and largely extends the absorption spectra to near-infrared region.Excited-state dynamics investigated via femto-and nano-second transient absorption spectroscopy revealed exclusive charge separation of the PBI-4Cz within initial 0.5 ps when photoexcited regardless of which intermediate is involved.Energy dissipation of the resulting charge-separated state(PBI^(•−)-4Cz^(•−))is subjected to the toggle between intersystem-crossing toward excited triplet states and charge recombination toward ground states.Relative importance of the two pathways can be tuned by micro-environmental polarity,which endows PBI-4Cz remarkable performances of singlet-oxygen generation(>90.0%)in toluene and photothermal conversion(∼28.6%)in DMSO.Harnessing intrinsic photostability and excited-state processes of heavy-atom-free PBI derivatives not only holds a promise for multifunctional phototheranostics,but also provides a prototype for designing high-performance PSs with tunable photoconversion pathways.

关键词： charge recombination charge separation perylene bisimide derivatives photosensitizers singlet oxygen generation

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