{"title":"Highly fluorescent, water-soluble tetrapodal perylene diimides insulated by cationic pendants for live-cell imaging","authors":"","doi":"10.1016/j.dyepig.2024.112460","DOIUrl":null,"url":null,"abstract":"<div><p>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 <strong>PDI-4Py-n</strong> 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.</p></div>","PeriodicalId":302,"journal":{"name":"Dyes and Pigments","volume":null,"pages":null},"PeriodicalIF":4.1000,"publicationDate":"2024-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Dyes and Pigments","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0143720824005266","RegionNum":3,"RegionCategory":"工程技术","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
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.
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.