Wu Yu-Huan, Zhang Jian, Du Fu-Sheng, Li Zi-Chen
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, Department of Polymer Science and Engineering, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
ACS Macro Lett. 2017 Dec 19;6(12):1398-1403. doi: 10.1021/acsmacrolett.7b00863. Epub 2017 Dec 1.
The selective Passerini reactions of 4-formylbenzoic acid and 4-isocyanobenzoic acid with aliphatic isocyanides and aldehydes were utilized to synthesize sequence-defined uniform macromolecules. Our strategy does not involve any protecting groups or reactive group transformation steps and allows direct and consecutive propagation of sequence in each step. Introduction of diverse side groups by using different aliphatic components provided a range of sequence-defined uniform macromolecules in high yield and gram scale. The strategy also allows further Passerini self-coupling or cross-coupling of the formed sequences with other small molecules, affording polymers with up to 5098.3 Da and 20 side groups. Thus, this strategy will show promise for more efficient synthesis of new sequence-defined macromolecules.
利用4-甲酰基苯甲酸和4-异氰基苯甲酸与脂肪族异氰化物和醛的选择性Passerini反应来合成序列定义的均匀大分子。我们的策略不涉及任何保护基团或反应性基团转化步骤，并且允许在每个步骤中直接且连续地进行序列延伸。通过使用不同的脂肪族组分引入多样的侧基，以高收率和克级规模得到了一系列序列定义的均匀大分子。该策略还允许所形成的序列与其他小分子进一步进行Passerini自偶联或交叉偶联，从而得到分子量高达5098.3 Da且具有20个侧基的聚合物。因此，该策略对于更高效地合成新的序列定义大分子具有广阔前景。
