Red Emissive Biocompatible Nanoparticles from Tetraphenylethene‐Decorated BODIPY Luminogens for Two‐Photon Excited Fluorescence Cellular Imaging and Mouse Brain Blood Vascular Visualization |
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| Authors: | Zujin Zhao Bin Chen Junlong Geng Zhengfeng Chang Laura Aparicio‐Ixta Han Nie Chi Ching Goh Lai Guan Ng Anjun Qin Gabriel Ramos‐Ortiz Bin Liu Ben Zhong Tang |
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| Affiliation: | 1. College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, , Hangzhou, 310036 China;2. Department of Chemical and Biomolecular Engineering, National University of Singapore, , Singapore, 117576;3. Centro de Investigaciones en óptica, , 37000 León, Gto., México;4. State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, , Guangzhou, 510640 China;5. Singapore Immunology Network (SIgN) A*STAR (Agency for Science Technology and Research), , Biopolis, 138648 Singapore;6. Department of Chemistry Institute for Advanced Study, State Key Laboratory of Molecular Neuroscience and Institute of Molecular Functional Materials, The Hong Kong University of Science & Technology Clear Water Bay, , Kowloon, Hong Kong, China |
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| Abstract: | BODIPY (4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene) is an emissive chromophore in solutions but suffers from fluorescence quenching when aggregated due to its flat molecular conformation and small Stokes shift. To create aggregate‐state emissive BODIPY luminogens, tetraphenylethene (TPE), which is a popular luminogen with intriguing aggregation‐induced emission (AIE) characteristic, is introduced as periphery to a methylated BODIPY core. Three TPE‐BODIPY adducts are synthesized and characterized, and their photophysical properties and electronic structures are investigated. The incorporation of AIE‐active TPE units alleviates aggregation‐caused quenching of BODIPY core, furnishing emissive nanoparticles based on TPE‐BODIPY adducts. Significantly, the two‐photon absorption (TPA) and two‐photon excited fluorescence (TPEF) properties are improved as more TPE units are attached. The luminogens with 3TPE units (3TPE‐BODIPY) shows the strongest TPA and TPEF in the wavelength range of 750–830 nm, with cross‐section values of 264 and 116 GM at 810 nm, respectively. Red emissive nanoparticles with a Stokes shift of 60 nm and a fluorescence quantum yield of 16% are attained by encapsulating 3TPE‐BODIPY with 1,2‐sistearoyl‐sn‐glycero‐3‐phosphoethanolamine‐N‐[methoxy(polyethylene glycol)‐2000]. The nanoparticles are biocompatible and function well in TPEF cellular imaging and mouse brain blood vascular visualization. |
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| Keywords: | BODIPY tetraphenylethene aggregation‐induced emission nanoparticle biological imaging |
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