Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers,Green Chemistry

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Synthesis of functional catechols as monomers of mussel-inspired biomimetic polymers
Green Chemistry ( IF 9.3 ) Pub Date : 2018-01-19 00:00:00 , DOI: 10.1039/c7gc03323k
Jiang Duan _{1,

2,

3,

4,

5} , Wenhai Wu _{1,

2,

3,

4,

5} , Zengfeng Wei _{1,

2,

3,

4,

5} , Dedou Zhu _{1,

2,

3,

4,

5} , Haiyang Tu _{1,

2,

3,

4,

5} , Aidong Zhang _{1,

2,

3,

4,

5}

Affiliation

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.

中文翻译：

贻贝启发的仿生聚合物单体的功能邻苯二酚的合成

近年来，含邻苯二酚的聚合物因其贻贝启发的多功能粘合功能而备受关注。我们在此报告了使用邻苯二酚与甲醛和仲胺的曼尼希反应，可轻松合成4- / 3-取代的邻苯二酚。该反应在没有任何催化剂的情况下在水中顺利进行。所需产物的分离对于该方法的成功很重要，这是通过pH控制的溶剂萃取和重结晶过程实现的。合成的官能邻苯二酚不仅表现出多巴胺样的氧化交联，而且具有可用于合成含邻苯二酚的聚合物的官能团。作为概念验证应用，有两种功能性邻苯二酚，

更新日期：2018-02-21

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