José G. Becerra-González , Eduardo Peña-Cabrera , José L. Belmonte-Vázquez
{"title":"从蓝色到红色。用单一荧光团达到全可见光谱:BODIPY","authors":"José G. Becerra-González , Eduardo Peña-Cabrera , José L. Belmonte-Vázquez","doi":"10.1016/j.tet.2024.134334","DOIUrl":null,"url":null,"abstract":"<div><div>BODIPYs (Boron-dipyrromethenes) are a class of fluorophores widely used in a plethora of scientific applications in material science and biomedicine due to their exceptional optical properties. The modulation of the absorption and emission wavelengths of BODIPYs is an area with significant growth opportunities, allowing these compounds to be tailored for specific applications. This review addresses different synthetic strategies that could modify their electronic and optical properties of the BODIPY core, mainly the absorption and emission wavelengths (λ<sub>abs</sub> = 422 nm - λ<sub>emis</sub> = 753 nm and quantum yields up to Φ<sub>c-hex</sub> = 100 %). These methodologies include reactions like nucleophilic substitutions with (chiral/achiral) primary and secondary amines, alkyl/aryl alcohols, active methylenes, as well as Liebeskind-Srogl, Sonogashira, Heck, and Suzuki cross-coupling reactions at the <em>meso</em> and peripheral positions of the BODIPY core. These synthetic strategies incorporate specific functional groups that influence the π-system conjugation, generation of AIEgens, and Donor-Acceptor (D-A) or Donor-Acceptor-Donor (D-A-D) architectures, enabling the labeling of biomolecules such as estrone and tyrosine.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134334"},"PeriodicalIF":2.1000,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"From blue to red. Reaching the full visible spectrum with a single fluorophore: BODIPY\",\"authors\":\"José G. Becerra-González , Eduardo Peña-Cabrera , José L. Belmonte-Vázquez\",\"doi\":\"10.1016/j.tet.2024.134334\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>BODIPYs (Boron-dipyrromethenes) are a class of fluorophores widely used in a plethora of scientific applications in material science and biomedicine due to their exceptional optical properties. The modulation of the absorption and emission wavelengths of BODIPYs is an area with significant growth opportunities, allowing these compounds to be tailored for specific applications. This review addresses different synthetic strategies that could modify their electronic and optical properties of the BODIPY core, mainly the absorption and emission wavelengths (λ<sub>abs</sub> = 422 nm - λ<sub>emis</sub> = 753 nm and quantum yields up to Φ<sub>c-hex</sub> = 100 %). These methodologies include reactions like nucleophilic substitutions with (chiral/achiral) primary and secondary amines, alkyl/aryl alcohols, active methylenes, as well as Liebeskind-Srogl, Sonogashira, Heck, and Suzuki cross-coupling reactions at the <em>meso</em> and peripheral positions of the BODIPY core. These synthetic strategies incorporate specific functional groups that influence the π-system conjugation, generation of AIEgens, and Donor-Acceptor (D-A) or Donor-Acceptor-Donor (D-A-D) architectures, enabling the labeling of biomolecules such as estrone and tyrosine.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"168 \",\"pages\":\"Article 134334\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-10-31\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024005155\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024005155","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
From blue to red. Reaching the full visible spectrum with a single fluorophore: BODIPY
BODIPYs (Boron-dipyrromethenes) are a class of fluorophores widely used in a plethora of scientific applications in material science and biomedicine due to their exceptional optical properties. The modulation of the absorption and emission wavelengths of BODIPYs is an area with significant growth opportunities, allowing these compounds to be tailored for specific applications. This review addresses different synthetic strategies that could modify their electronic and optical properties of the BODIPY core, mainly the absorption and emission wavelengths (λabs = 422 nm - λemis = 753 nm and quantum yields up to Φc-hex = 100 %). These methodologies include reactions like nucleophilic substitutions with (chiral/achiral) primary and secondary amines, alkyl/aryl alcohols, active methylenes, as well as Liebeskind-Srogl, Sonogashira, Heck, and Suzuki cross-coupling reactions at the meso and peripheral positions of the BODIPY core. These synthetic strategies incorporate specific functional groups that influence the π-system conjugation, generation of AIEgens, and Donor-Acceptor (D-A) or Donor-Acceptor-Donor (D-A-D) architectures, enabling the labeling of biomolecules such as estrone and tyrosine.
期刊介绍:
Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry.
Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters.
Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.