Aggregation Behavior of CHR-bis(BODIPY) Bichromophores in THF-water Mixtures: Effect of Linking Positions and Aryl-spacer Substituents.

IF 2.6 4区 化学 Q2 BIOCHEMICAL RESEARCH METHODS
Artem S Sherudillo, Alexander A Kalyagin, Lubov A Antina, Mikhail B Berezin, Elena V Antina
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引用次数: 0

Abstract

Aggregation-caused quenching effect (ACQ) greatly limits the practical use of many organic luminophores in biomedicine, optics and electronics. The comparative analysis of aggregation characteristics of CHR-bis(BODIPY) bichromophores 1-6 with R = H, Ph, MeOPh and various linking positions (α,α-; α,β-; β,β- and β',β'-) in THF-water mixtures with different water fractions or dye concentrations is first presented in this article. Both the linking style 1-4 and the arylation of the spacer with phenyl (Ph-) 5 or methoxyphenyl (MeOPh-) 6 substituents strongly affect the formation of luminophore aggregated forms in binary THF-water mixtures. The α,α-and β,β-isomers (1 and 3) form non-fluorescent H-type aggregates in THF-water mixtures with fw > 70%. The α,β-; β',β'-isomers (2, 4) and the MeOPh-substituted β,β-bichromophore 6 are characterized by predominant formation fluorescent aggregates. All bichromophores are characterized by the presence of residual amounts of non-aggregated forms in binary mixtures with maximum water content. The results are useful for controlling the aggregation behavior and spectral characteristics of CHR-bis(BODIPY) bichromophores in aqueous-organic media, which is important in the development of biomarkers and PDT agents.

CHR 双(BODIPY)重色团在 THF-水混合物中的聚合行为:连接位置和芳基间隔取代基的影响。
聚集引起的淬灭效应(ACQ)极大地限制了许多有机发光体在生物医学、光学和电子学领域的实际应用。本文首次比较分析了 R = H、Ph、MeOPh 和不同连接位置(α,α-;α,β-;β,β- 和 β',β'-)的 CHR-双(BODIPY)双色素 1-6 在不同水组分或染料浓度的 THF-水混合物中的聚集特性。连接方式 1-4 和间隔物与苯基 (Ph-) 5 或甲氧基苯基 (MeOPh-) 6 取代基的芳基化都会强烈影响二元 THF 水混合物中发光体聚集形式的形成。在 fw > 70% 的四氢呋喃-水混合物中,α,α 和 β,β- 异构体(1 和 3)形成无荧光的 H 型聚集体。α,β-;β',β'-异构体(2、4)和 MeOPh 取代的 β,β-双色团 6 主要形成荧光聚集体。在含水量最大的二元混合物中,所有双色体都存在残余的非聚集形式。研究结果有助于控制 CHR-双(BODIPY)双色素在水有机介质中的聚集行为和光谱特征,这对于开发生物标记物和光导放疗剂非常重要。
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来源期刊
Journal of Fluorescence
Journal of Fluorescence 化学-分析化学
CiteScore
4.60
自引率
7.40%
发文量
203
审稿时长
5.4 months
期刊介绍: Journal of Fluorescence is an international forum for the publication of peer-reviewed original articles that advance the practice of this established spectroscopic technique. Topics covered include advances in theory/and or data analysis, studies of the photophysics of aromatic molecules, solvent, and environmental effects, development of stationary or time-resolved measurements, advances in fluorescence microscopy, imaging, photobleaching/recovery measurements, and/or phosphorescence for studies of cell biology, chemical biology and the advanced uses of fluorescence in flow cytometry/analysis, immunology, high throughput screening/drug discovery, DNA sequencing/arrays, genomics and proteomics. Typical applications might include studies of macromolecular dynamics and conformation, intracellular chemistry, and gene expression. The journal also publishes papers that describe the synthesis and characterization of new fluorophores, particularly those displaying unique sensitivities and/or optical properties. In addition to original articles, the Journal also publishes reviews, rapid communications, short communications, letters to the editor, topical news articles, and technical and design notes.
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