Fei Yang, Ran Li, Prof. Wei Wei, Dr. Xingwei Ding, Dr. Zhenzhen Xu, Ping Wang, Dr. Guo Wang, Dr. Yanqing Xu, Prof. Hongbing Fu, Prof. Yanli Zhao
{"title":"Water-Soluble Doubly-Strapped Isolated Perylene Diimide Chromophore","authors":"Fei Yang, Ran Li, Prof. Wei Wei, Dr. Xingwei Ding, Dr. Zhenzhen Xu, Ping Wang, Dr. Guo Wang, Dr. Yanqing Xu, Prof. Hongbing Fu, Prof. Yanli Zhao","doi":"10.1002/ange.202202491","DOIUrl":null,"url":null,"abstract":"<p>Perylene diimides (PDIs), a well-studied class of organic dyes, have a strong tendency to self-aggregate in water, thus greatly restricting their phototheranostic applications. Herein, we report a water-soluble PDI cyclophane “Gemini Box” (<b>GBox-1<sup>4+</sup></b>), consisting of a central PDI chromophore enclosed by double-sided cationic molecular straps. Owing to the effective spatial isolation, the chromophore self-aggregation can be completely eliminated, even in a concentrated aqueous solution up to 2 mM. To our knowledge, <b>GBox-1<sup>4+</sup></b> represents an interesting example of a fluorescent PDI cyclophane in water, capable of being employed for lysosome-targetable live-cell imaging. More importantly, the highly concentrated aqueous solution of PDI radical anion can be significantly stabilized by <b>GBox-1<sup>4+</sup></b> to exhibit an excellent near-infrared photothermal effect, which was further exploited for efficient and selective antibacterial applications. This work provides a new access to water-soluble non-aggregated organic dyes and promotes their potential biomedical applications.</p>","PeriodicalId":7803,"journal":{"name":"Angewandte Chemie","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2022-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ange.202202491","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Perylene diimides (PDIs), a well-studied class of organic dyes, have a strong tendency to self-aggregate in water, thus greatly restricting their phototheranostic applications. Herein, we report a water-soluble PDI cyclophane “Gemini Box” (GBox-14+), consisting of a central PDI chromophore enclosed by double-sided cationic molecular straps. Owing to the effective spatial isolation, the chromophore self-aggregation can be completely eliminated, even in a concentrated aqueous solution up to 2 mM. To our knowledge, GBox-14+ represents an interesting example of a fluorescent PDI cyclophane in water, capable of being employed for lysosome-targetable live-cell imaging. More importantly, the highly concentrated aqueous solution of PDI radical anion can be significantly stabilized by GBox-14+ to exhibit an excellent near-infrared photothermal effect, which was further exploited for efficient and selective antibacterial applications. This work provides a new access to water-soluble non-aggregated organic dyes and promotes their potential biomedical applications.