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基于苯并噻唑衍生物的聚集诱导发光:光稳定的开启型生物成像

Aggregation tailored emission of a benzothiazole based derivative: photostable turn on bioimaging.

作者信息

Kaur Ishpreet, Sharma Vinay, Mobin Shaikh M, Khajuria Anjali, Ohri Puja, Kaur Paramjit, Singh Kamaljit

机构信息

Department of Chemistry, UGC-Centre of Advanced Study Guru Nanak Dev University Amritsar 143005 India

Discipline of Biosciences and Bio-Medical Engineering, Indian Institute of Technology Indore Simrol, Khandwa Road Indore 453552 India.

出版信息

RSC Adv. 2019 Dec 4;9(68):39970-39975. doi: 10.1039/c9ra08149f. eCollection 2019 Dec 2.

Abstract

Herein, we report a benzothiazole based probe which exhibits aggregation induced emission in mixed solvents, v/v THF : water system. The blue emission observed in the solution is ascribed to the enolic emission of the excited state intramolecular proton transfer (ESIPT) prone benzothiazole chromophore, as the aggregation induced by the protic solvent, water, is expected to restrict the phototautomerization of the probe to the keto form which generally emits in the red region. However, the green emission observed in the solid aggregated state is ascribed to its keto emission, as in the solid state the ESIPT process is activated owing to stable intramolecular hydrogen bonding, giving a keto-aggregation induced emission (AIE) coupled emission. The aggregation process is evident from the particle size and the change in morphology predicted by dynamic light scattering (DLS) and scanning electron microscopy (SEM) respectively, in the aggregated state. Interestingly, the emission in the solution, as well as the solid state, is convincingly mimicked in the fluorescence imaging of various live cancer cells and plant roots.

摘要

在此,我们报道了一种基于苯并噻唑的探针,它在混合溶剂(体积比为四氢呋喃:水的体系)中表现出聚集诱导发光。溶液中观察到的蓝色发射归因于易于发生激发态分子内质子转移(ESIPT)的苯并噻唑发色团的烯醇式发射,因为质子性溶剂水诱导的聚集预计会限制探针向通常在红色区域发射的酮式形式的光互变异构。然而,在固体聚集态中观察到的绿色发射归因于其酮式发射,因为在固态中,由于稳定的分子内氢键,ESIPT过程被激活,产生酮聚集诱导发光(AIE)耦合发射。通过动态光散射(DLS)和扫描电子显微镜(SEM)分别预测的聚集态下的粒径和形态变化表明了聚集过程。有趣的是,在各种活癌细胞和植物根的荧光成像中,溶液态以及固态的发射都得到了令人信服的模拟。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b9e4/9076209/ae479dbd65d7/c9ra08149f-f1.jpg

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