Highly fluorescent, water-soluble tetrapodal perylene diimides insulated by cationic pendants for live-cell imaging

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2024-09-14 DOI:10.1016/j.dyepig.2024.112460

Xiangkun Cui , Bojun Shi , Zixuan Qiu , Fei Yang , Xiuteng Wang , Yanqing Xu , Wei Wei

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Abstract

Perylene diimides (PDIs), particularly the parent core-unsubstituted PDI chromophores, exhibit a pronounced tendency to aggregate in water, resulting in significant fluorescence quenching. Herein we present a new class of highly fluorescent, water-soluble tetrapodal PDI dyes PDI-4Py-n, with the chromophore core surrounded by four pyridinium pendants, which have been fully characterized by several techniques including X-ray crystallography. Due to the spatial isolation and charge repulsion from four cationic pendants, PDI-4Py-n can effectively suppress the chromophore aggregation in relatively concentrated aqueous solutions, thereby preserving the characteristic PDI fluorescence with high photoluminescence quantum yield. Owing to the outstanding fluorescence properties and good biocompatibility, one of PDI-4Py-n has been successfully employed as a lysosome-targetable fluorescent probe for live-cell imaging. This work presents a straightforward synthetic strategy to water-soluble non-aggregating organic dyes and highlights their potential for biomedical applications.

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由阳离子垂体绝缘的高荧光、水溶性四元过二亚胺，用于活细胞成像

过二亚胺（PDI），尤其是母核未取代的 PDI 发色团，在水中有明显的聚集倾向，从而导致显著的荧光淬灭。在此，我们提出了一类新型的高荧光、水溶性四极 PDI 染料 PDI-4Py-n，其发色团核心被四个吡啶鎓垂体包围，并通过 X 射线晶体学等多种技术对其进行了全面表征。由于四个阳离子垂体的空间隔离和电荷排斥作用，PDI-4Py-n 能在相对浓的水溶液中有效抑制发色团的聚集，从而保持 PDI 特有的高光量子产率荧光。由于 PDI-4Py-n 具有出色的荧光特性和良好的生物相容性，已被成功地用作溶酶体靶向荧光探针，用于活细胞成像。这项研究提出了一种直接合成水溶性非聚合有机染料的策略，并强调了它们在生物医学应用方面的潜力。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.