From blue to red. Reaching the full visible spectrum with a single fluorophore: BODIPY

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2024-10-31 DOI:10.1016/j.tet.2024.134334

José G. Becerra-González , Eduardo Peña-Cabrera , José L. Belmonte-Vázquez

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Abstract

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_abs = 422 nm - λ_emis = 753 nm and quantum yields up to Φ_c-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.

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从蓝色到红色。用单一荧光团达到全可见光谱：BODIPY

BODIPYs （硼二吡咯烷酮）是一类荧光体，由于其优异的光学特性，被广泛应用于材料科学和生物医学领域的大量科学应用中。对 BODIPYs 的吸收和发射波长进行调节是一个具有重大发展机遇的领域，可使这些化合物适合特定应用。本综述探讨了可改变 BODIPY 核心的电子和光学特性，主要是吸收和发射波长（λabs = 422 nm - λemis = 753 nm，量子产率可达 Φc-hex = 100 %）的不同合成策略。这些方法包括与（手性/非手性）伯胺和仲胺、烷基/芳基醇、活性亚甲基等发生亲核取代反应，以及在 BODIPY 核心的中间和外围位置发生 Liebeskind-Srogl、Sonogashira、Heck 和 Suzuki 交叉偶联反应。这些合成策略结合了特定的官能团，可影响π系统共轭、AIEgens 的生成以及供体-受体（D-A）或供体-受体-供体（D-A-D）结构，从而实现对雌酮和酪氨酸等生物大分子的标记。

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

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.