Design and Synthesis of Monofunctionalized, Water-Soluble Conjugated Polymers for Biosensing and Imaging Applications,Journal of the American Chemical Society

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Design and Synthesis of Monofunctionalized, Water-Soluble Conjugated Polymers for Biosensing and Imaging Applications
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2011-08-17 , DOI: 10.1021/ja202877q
Christopher A. Traina ₁ , Ronald C. Bakus ₁ , Guillermo C. Bazan ₁

Affiliation

Water-soluble conjugated polymers with controlled molecular weight characteristics, absence of ionic groups, high emission quantum yields, and end groups capable of selective reactions of wide scope are desirable for improving their performance in various applications and, in particular, fluorescent biosensor schemes. The synthesis of such a structure is described herein. 2-Bromo-7-iodofluorene with octakis(ethylene glycol) monomethyl ether chains at the 9,9'-positions, i.e., compound 4, was prepared as the reactive premonomer. A high-yielding synthesis of the organometallic initiator (dppe)Ni(Ph)Br (dppe = 1,2-bis(diphenylphosphino)ethane) was designed and implemented, and the resulting product was characterized by single-crystal X-ray diffraction techniques. Polymerization of 4 by (dppe)Ni(Ph)Br can be carried out in less than 30 s, affording excellent control over the average molecular weight and polydispersity of the product. Quenching of the polymerization with [2-(trimethylsilyl)ethynyl]magnesium bromide yields silylacetylene-terminated water-soluble poly(fluorene) with a photoluminescence quantum efficiency of 80%. Desilylation, followed by copper-catalyzed azide-alkyne cycloaddition reaction, yields a straightforward route to introduce a wide range of specific end group functionalities. Biotin was used as an example. The resulting biotinylated conjugated polymer binds to streptavidin and acts as a light-harvesting chromophore to optically amplify the emission of Alexa Fluor-488 chromophores bound onto the streptavidin. Furthermore, the biotin end group makes it possible to bind the polymer onto streptavidin-functionalized cross-linked agarose beads and thereby incorporate a large number of optically active segments.

中文翻译：

用于生物传感和成像应用的单功能化水溶性共轭聚合物的设计和合成

水溶性共轭聚合物具有可控的分子量特性、不存在离子基团、高发射量子产率和能够在广泛范围内选择性反应的端基，对于提高它们在各种应用中的性能，特别是荧光生物传感器方案，是可取的。本文描述了这种结构的合成。在 9,9'-位具有八（乙二醇）单甲醚链的 2-Bromo-7-iodofluorene，即化合物 4，被制备为反应性预单体。设计并实现了有机金属引发剂 (dppe)Ni(Ph)Br（dppe = 1,2-双（二苯基膦）乙烷）的高产合成，并通过单晶 X 射线衍射技术表征了所得产物. (dppe)Ni(Ph)Br 聚合 4 可在不到 30 秒内进行，对产品的平均分子量和多分散性提供极好的控制。用 [2-(三甲基甲硅烷基) 乙炔基] 溴化镁淬灭聚合反应，产生具有 80% 光致发光量子效率的甲硅烷基乙炔封端的水溶性聚（芴）。脱甲硅烷基化，然后是铜催化的叠氮化物-炔烃环加成反应，产生了一条引入多种特定端基官能团的直接途径。以生物素为例。生成的生物素化共轭聚合物与链霉亲和素结合，并作为捕光发色团，光学放大与链霉亲和素结合的 Alexa Fluor-488 发色团的发射。此外，

更新日期：2011-08-17

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