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Thiol-Ene Networks from Sequence-Defined Polyurethane Macromers
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-03-23 , DOI: 10.1021/jacs.0c00759 Emily A. Hoff 1 , Guilhem X. De Hoe 2 , Christopher M. Mulvaney 1 , Marc A. Hillmyer 2 , Christopher A. Alabi 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-03-23 , DOI: 10.1021/jacs.0c00759 Emily A. Hoff 1 , Guilhem X. De Hoe 2 , Christopher M. Mulvaney 1 , Marc A. Hillmyer 2 , Christopher A. Alabi 1
Affiliation
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To date, scalability limitations have hindered the exploration and application of sequence-defined polymers in areas such as syn-thetic plastics, fibers, rubbers, coatings, and composites. Additionally, the impact of sequence on the properties of cross-linked networks remains largely unknown. To address the need for synthetic methods to generate sequence-defined materials in gram quantities, we have developed a strategy involving inexpensive and readily functional vanillin-based monomers to assemble se-quence-defined polyurethane oligomers via sequential reductive amination and carbamation. Three oligomers were synthesized with monomer sequence precisely dictated by the placement of reactive side chains during the reductive amination reaction. Avoiding excessive chromatographic purification and solid- or liquid-phase supports enabled synthesis of sequence-defined oligo-mers on the gram-scale. Remarkably, sequence was shown to influence network topology upon cross-linking as evidenced by se-quence-dependent rubbery moduli values. This work provides one of the first examples of a scalable synthetic route towards se-quence-defined thermosets that exhibit sequence-dependent properties.
中文翻译：
来自序列定义的聚氨酯大分子单体的硫醇-烯网络
迄今为止，可扩展性限制阻碍了序列定义聚合物在合成塑料、纤维、橡胶、涂料和复合材料等领域的探索和应用。此外，序列对交联网络特性的影响在很大程度上仍然未知。为了满足对以克为单位生成序列定义材料的合成方法的需求，我们开发了一种策略，该策略涉及廉价且易于使用的功能性香草醛基单体，通过顺序还原胺化和氨基甲酸酯化来组装序列定义的聚氨酯低聚物。合成了三种低聚物，其单体序列由还原胺化反应过程中反应性侧链的位置精确决定。避免过度的色谱纯化和固相或液相支持，能够以克级规模合成序列定义的寡聚体。值得注意的是，序列显示出在交联时影响网络拓扑结构，这由依赖于序列的橡胶模量值证明。这项工作提供了可扩展合成路线的第一个例子，该路线可实现序列定义的热固性材料，这些热固性材料具有序列相关特性。
更新日期：2020-03-23
中文翻译：
来自序列定义的聚氨酯大分子单体的硫醇-烯网络
迄今为止，可扩展性限制阻碍了序列定义聚合物在合成塑料、纤维、橡胶、涂料和复合材料等领域的探索和应用。此外，序列对交联网络特性的影响在很大程度上仍然未知。为了满足对以克为单位生成序列定义材料的合成方法的需求，我们开发了一种策略，该策略涉及廉价且易于使用的功能性香草醛基单体，通过顺序还原胺化和氨基甲酸酯化来组装序列定义的聚氨酯低聚物。合成了三种低聚物，其单体序列由还原胺化反应过程中反应性侧链的位置精确决定。避免过度的色谱纯化和固相或液相支持，能够以克级规模合成序列定义的寡聚体。值得注意的是，序列显示出在交联时影响网络拓扑结构，这由依赖于序列的橡胶模量值证明。这项工作提供了可扩展合成路线的第一个例子，该路线可实现序列定义的热固性材料，这些热固性材料具有序列相关特性。
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