A Red to Near‐IR Fluorogen: Aggregation‐Induced Emission, Large Stokes Shift, High Solid Efficiency and Application in Cell‐Imaging
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- Yi Jia Wang
- MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China
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- Yang Shi
- MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China
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- Zhaoyang Wang
- MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China
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- Zhenfeng Zhu
- State Key Laboratory of Modern Optical Instrumentation Centre for Optical and Electromagnetic Research Zhejiang Provincial Key Laboratory for Sensing Technologies JORCEP (Sino-Swedish Joint Research Centre of Photonics) Zhejiang University Hangzhou 310058 China
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- Xinyuan Zhao
- Institute of Environmental Health Zhejiang University Hangzhou 310058 China
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- Han Nie
- Guangdong Innovative Research Team State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 China
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- Jun Qian
- State Key Laboratory of Modern Optical Instrumentation Centre for Optical and Electromagnetic Research Zhejiang Provincial Key Laboratory for Sensing Technologies JORCEP (Sino-Swedish Joint Research Centre of Photonics) Zhejiang University Hangzhou 310058 China
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- Anjun Qin
- Guangdong Innovative Research Team State Key Laboratory of Luminescent Materials and Devices South China University of Technology Guangzhou 510640 China
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- Jing Zhi Sun
- MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China
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- Ben Zhong Tang
- MoE Key Laboratory of Macromolecule Synthesis and Functionalization Department of Polymer Science and Engineering Zhejiang University Hangzhou 310027 China
抄録
<jats:title>Abstract</jats:title><jats:p>A tetraphenylethene (TPE) derivative modified with the strong electron acceptor 2‐dicyano‐methylene‐3‐cyano‐4,5,5‐trimethyl‐2,5‐dihydrofuran (TCF) was obtained in high yield by a simple two‐step reaction. The resultant TPE‐TCF showed evident aggregation‐induced emission (AIE) features and pronounced solvatochromic behavior. Changing the solvent from apolar cyclohexane to highly polar acetonitrile, the emission peak shifted from 560 to 680 nm (120 nm redshift). In an acetonitrile solution and in the solid powder, the Stokes shifts are as large as 230 and 190 nm, respectively. The solid film emits red to near‐IR (red‐NIR) fluorescence with an emission peak at 670 nm and a quantum efficiency of 24.8 %. Taking the advantages of red‐NIR emission and high efficiency, nanoparticles (NPs) of TPE‐TCF were fabricated by using tat‐modified 1,2‐distearoylsn‐glycero‐3‐phosphor‐ethanol‐amine‐<jats:italic>N</jats:italic>‐[methoxy‐(polyethyl‐eneglycol)‐2000] as the encapsulation matrix. The obtained NPs showed perfect membrane penetrability and high fluorescent imaging quality of cell cytoplasm. Upon co‐incubation with 4,6‐diamidino‐2‐phenylindole (DAPI) in the presence of tritons, the capsulated TPE‐TCF nanoparticles could enter into the nucleus and displayed similar staining properties to those of DAPI.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 22 (28), 9784-9791, 2016-06-06
Wiley