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一种新型吡啶鎓修饰的四苯乙烯:聚集诱导发光活性、机械变色、DNA检测及线粒体成像

A novel pyridinium modified tetraphenylethene: AIE-activity, mechanochromism, DNA detection and mitochondrial imaging.

作者信息

Wang Zhaoyang, Gu Yuan, Liu Junyuan, Cheng Xiao, Sun Jing Zhi, Qin Anjun, Tang Ben Zhong

机构信息

MOE Key Laboratory of Macromolecular Synthesis and Functionalization, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, China.

出版信息

J Mater Chem B. 2018 Feb 28;6(8):1279-1285. doi: 10.1039/c7tb03012f. Epub 2018 Feb 12.

DOI:10.1039/c7tb03012f
PMID:32254189
Abstract

We report the design and synthesis of a novel cationic AIE-gen, i.e., (E)-TPEDEPy-DBz, which can be derived from a facile synthetic route. (E)-TPEDEPy-DBz is a stereo-pure isomer and shows evident AIE properties with yellow-greenish emission in the solid state (Φ = 43.7%). Distinct from most of the ionic AIE-gens reported in the literature, which are usually exemplified by their water solubility and the capacity for interaction with charged biological species, (E)-TPEDEPy-DBz demonstrated moderate solvatochromism and evident mechanoluminochromism behaviours. The emission of (E)-TPEDEPy-DBz can be switched between yellow-greenish in the crystalline state to red-orange in the amorphous state by grinding and fuming treatments. Due to the AIE-characteristics, cationic modification and the thus-acquired water solubility, (E)-TPEDEPy-DBz performed as a sensitive fluorescent probe to detect DNA in Tris-HCl buffer solution. More importantly, (E)-TPEDEPy-DBz showed good membrane permeability and cell viability, and the potentiality to be used as a mitochondria-specific probe working in a fluorescence turn-on mode.

摘要

我们报道了一种新型阳离子聚集诱导发光(AIE)分子(E)-TPEDEPy-DBz的设计与合成,其可通过简便的合成路线获得。(E)-TPEDEPy-DBz是一种立体纯异构体,在固态下呈现明显的AIE性质,发出黄绿色荧光(Φ = 43.7%)。与文献中报道的大多数离子型AIE分子不同,后者通常以其水溶性和与带电生物分子相互作用的能力为特征,(E)-TPEDEPy-DBz表现出适度的溶剂化显色和明显的机械发光变色行为。通过研磨和熏蒸处理,(E)-TPEDEPy-DBz的发射可以从结晶态的黄绿色切换到非晶态的红橙色。由于其AIE特性、阳离子修饰以及由此获得的水溶性,(E)-TPEDEPy-DBz在Tris-HCl缓冲溶液中作为检测DNA的灵敏荧光探针。更重要的是,(E)-TPEDEPy-DBz表现出良好的膜通透性和细胞活力,具有用作线粒体特异性探针以荧光开启模式工作的潜力。

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