Efficient Metal-Free Norbornadiene–Maleimide Click Reaction for the Formation of Molecular Bottlebrushes,Macromolecules

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Efficient Metal-Free Norbornadiene–Maleimide Click Reaction for the Formation of Molecular Bottlebrushes
Macromolecules ( IF 5.1 ) Pub Date : 2021-10-22 , DOI: 10.1021/acs.macromol.1c01776
Zheqi Li _{1,

2} , Wangmeng Hou ₂ , Yuanchao Li ₂ , Jianxiong Xu ₁ , Yi Shi ₂ , Yongming Chen ₂

Affiliation

A highly efficient metal-free grafting-onto strategy based on the cyclopentadiene (Cp)–maleimide click reaction was developed for the preparation of molecular bottlebrushes (MBBs) with diverse morphologies and compositions. First, the masked Cp units, norbornadiene (NBD) groups, were introduced onto poly(2-hydroxyethyl acrylate) (PHEA) as repeated anchoring groups to produce the PHEA–NBD backbone-to-be with different degrees of polymerization (DPs). Meanwhile, maleimide-terminated polyethylene glycol, poly(tert-butyl acrylate), poly(N,N-dimethylacrylamide), and poly(N,N-dimethylaminoethyl acrylate) were synthesized as side chains (SCs). Subsequently, the metal-free NBD–Mal click reaction under mild conditions was applied for preparing the MBBs with a tunable morphology and various functionalities. The grafting density was affected by the concentration and composition of the SCs. When the concentration of the SC was 0.06 M, the grafting density can reach up to 92% at the feed ratio of [Mal]/[NBD] = 1:1 and increase to 100% at the feed ratio of [Mal]/[NBD] = 1.5:1. Atomic force microscopy characterization indicated that the morphology of the obtained MBBs could be tuned from rodlike to wormlike by variation of the DP of the backbone from 105 to 419.

中文翻译：

用于形成分子瓶刷的高效无金属降冰片二烯-马来酰亚胺点击反应

开发了一种基于环戊二烯（Cp）-马来酰亚胺点击反应的高效无金属接枝策略，用于制备具有多种形态和组成的分子瓶刷（MBB）。首先，将掩蔽的 Cp 单元降冰片二烯 (NBD) 基团作为重复的锚定基团引入到聚 (2-羟乙基丙烯酸酯) (PHEA) 上，以产生具有不同聚合度 (DP) 的 PHEA-NBD 主链。同时，马来酰亚胺封端的聚乙二醇、聚（丙烯酸叔丁酯）、聚（N，N-二甲基丙烯酰胺）和聚（N，N-二甲基氨基乙基丙烯酸酯）合成为侧链（SC）。随后，在温和条件下应用无金属 NBD-Mal 点击反应制备具有可调形态和各种功能的 MBB。接枝密度受 SCs 的浓度和组成的影响。当SC的浓度为0.06 M时，[Mal]/[NBD] = 1:1的进料比下接枝密度可达92%，[Mal]/[进料比增加到100%。 NBD] = 1.5:1。原子力显微镜表征表明，通过将主链的 DP 从 105 变化到 419，可以将获得的 MBB 的形态从棒状调整为蠕虫状。

更新日期：2021-11-09

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