Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers
Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers
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功能性儿茶酚作为贻贝仿生聚合物单体的合成
DOI：
10.1039/c7gc03323k
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发表时间：
2018-02-21
期刊：
影响因子：
9.8
通讯作者：
Zhang, Aidong
中科院分区：
文献类型：
--
作者：
Duan, Jiang;Wu, Wenhai;Zhang, Aidong
近年来，含邻苯二酚的聚合物由于其多功能的贻贝型粘合剂功能而引起了人们的广泛关注。我们在本文中报告了使用邻苯二酚与甲醛和仲胺的曼尼希反应轻松合成4-/3-取代邻苯二酚。该反应在水中进行顺利，没有任何催化剂。所需产物的分离对于该方法的成功是重要的，并且通过pH控制的溶剂萃取和重结晶过程来实现。所合成的功能性儿茶酚不仅具有类似多巴胺的氧化交联作用，而且还具有可用于合成含儿茶酚聚合物的功能基团。作为概念验证应用，将两种功能性儿茶酚（一种在4-氨甲基取代基处具有单羟基，另一种在4-氨甲基取代基处具有二羟基）分别掺入聚丙烯酸酯和聚氨酯主链中，赋予这些聚合物在各种表面上优异的可涂布性。
Catechol-containing polymers have attracted much attention in recent years because of their versatile mussel-inspired adhesive function. We report herein the facile synthesis of 4-/3-substituted catechols using the Mannich reaction of catechol with formaldehyde and secondary amines. The reaction proceeds smoothly in water without any catalyst. Separation of the desired products is important for the success of this methodology, and was achieved by a pH-controlled solvent extraction and recrystallization process. The synthesized functional catechols not only exhibited dopamine-like oxidative cross-linking, but also possessed functional groups that are useful for the synthesis of catechol-containing polymers. As a proof-of-concept application, two functional catechols, one bearing monohydroxyl and the other bearing dihydroxyl groups at the 4-aminomethyl substituent, were incorporated into polyacrylate and polyurethane backbones, respectively, endowing these polymers with excellent coatability on various surfaces.