Chunyan Song, Zhenhui Wei, Yongsheng Zhang, Muqian Li, Junbo Gong
{"title":"Chiral Boron Dipyrromethene Dye with Acid-Responsive Near-Infrared Emission and Chiral Optical Behavior","authors":"Chunyan Song, Zhenhui Wei, Yongsheng Zhang, Muqian Li, Junbo Gong","doi":"10.1002/cplu.202500237","DOIUrl":null,"url":null,"abstract":"<p>A chiral boron dipyrromethene (BODIPY) dye, denoted as (<i>R</i>)-<b>2</b>, incorporating near-infrared (NIR) emission and chiral optical behavior, is synthesized. The dye is engineered by coupling polyethylene glycol chains with <i>R</i>-stereogenic centers to a donor–acceptor BODIPY core through a Suzuki coupling reaction. This modification significantly enhances the solubility and facilitates efficient chirality transfer resulting in distinct circular dichroism (CD) activity, which is quite remarkable in organic small molecule solutions. Furthermore, acid-triggered protonation of the dye leads to a bathochromic shift in the maximum absorption wavelength (from 633 to 664 nm) and an increase in NIR emission intensity, which is attributed to the enhanced intramolecular charge transfer in solution.</p>","PeriodicalId":148,"journal":{"name":"ChemPlusChem","volume":"90 7","pages":""},"PeriodicalIF":2.8000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemPlusChem","FirstCategoryId":"92","ListUrlMain":"https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202500237","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
A chiral boron dipyrromethene (BODIPY) dye, denoted as (R)-2, incorporating near-infrared (NIR) emission and chiral optical behavior, is synthesized. The dye is engineered by coupling polyethylene glycol chains with R-stereogenic centers to a donor–acceptor BODIPY core through a Suzuki coupling reaction. This modification significantly enhances the solubility and facilitates efficient chirality transfer resulting in distinct circular dichroism (CD) activity, which is quite remarkable in organic small molecule solutions. Furthermore, acid-triggered protonation of the dye leads to a bathochromic shift in the maximum absorption wavelength (from 633 to 664 nm) and an increase in NIR emission intensity, which is attributed to the enhanced intramolecular charge transfer in solution.
期刊介绍：
ChemPlusChem is a peer-reviewed, general chemistry journal that brings readers the very best in multidisciplinary research centering on chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
Fully comprehensive in its scope, ChemPlusChem publishes articles covering new results from at least two different aspects (subfields) of chemistry or one of chemistry and one of another scientific discipline (one chemistry topic plus another one, hence the title ChemPlusChem). All suitable submissions undergo balanced peer review by experts in the field to ensure the highest quality, originality, relevance, significance, and validity.
京公网安备 11010802042870号
京ICP备2023020795号-1
分享
求助内容：
应助结果提醒方式：
扫码关注我们
