Solid-phase methods for the synthesis of cyanine dyes
Solid-phase methods for the synthesis of cyanine dyes
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DOI：
10.1021/jo0479415
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发表时间：
2005-04-15
影响因子：
3.6
通讯作者：
Balasubramanian, S
中科院分区：
文献类型：
--
作者：
Mason, SJ;Hake, JL;Balasubramanian, S
我们在这里报告了一系列的研究，探索固相方法合成各种菁染料。先前报道的使用磺酰氯树脂（1）的捕获和释放方法的范围现在已经扩展到包括五甲川和水溶性花青染料。我们还报告了一个新的和化学上不同的合成策略，采用固定化的多烯链前体上的杂环碳亲核试剂的逐步攻击，允许从更容易获得的起始材料清洁合成疏水性和亲水性三次甲基和五次甲基染料。总的来说，这两种方法似乎是强大的和通用的策略，以提供广泛的高纯度的菁基染料。
We report here a series of studies that explore solid-phase methodologies for the synthesis of various cyanine dyes. The scope of the previously reported catch-and-release method using sulfonyl chloride resin(1) has now been extended to include pentamethine and water-soluble cyanine dyes. We also report a new and chemically distinct synthetic strategy, employing the stepwise attack of heterocyclic carbon nucleophiles on immobilized polyene-chain precursors, allowing the clean synthesis of hydrophobic and hydrophilic trimethine and pentamethine dyes from more easily obtained starting materials. Overall, both approaches appear to be robust and versatile strategies to delivering a wide range of cyanine-based dyes in high purity.