Combining Orthogonal Chain-End Deprotections and Thiol–Maleimide Michael Coupling: Engineering Discrete Oligomers by an Iterative Growth Strategy
Zhihao Huang1, Junfei Zhao1, Zimu Wang1, Fanying Meng1, Kunshan Ding1, Xiangqiang Pan1, Nianchen Zhou1, Xiaopeng Li2, Zhengbiao Zhang*1(张正彪), and Xiulin Zhu1
1State and Local Joint Engineering Laboratory for Novel Functional
Polymeric Materials, Jiangsu Key Laboratory of Advanced Functional
Polymer Design and Application, College of Chemistry
Chemical Engineering and Materials Science, Soochow University
Suzhou, 215123 (China)
2Department of Chemistry, University of South Florida, Tampa
Florida, 33620 (USA)
Angew. Chem. Int. Ed. 2017, 56, 13612 --13617
Orthogonal maleimide and thiol deprotections were combined with thiol–maleimide coupling to synthesize discrete oligomers/macromolecules on a gram scale with molecular weights up to 27.4 kDa (128mer, 7.9 g) using an iterative exponential growth strategy with a degree of polymerization (DP) of 2n−1. Using the same chemistry, a “readable” sequence-defined oligomer and a discrete cyclic topology were also created. Furthermore, uniform dendrons were fabricated using sequential growth (DP=2n−1) or double exponential dendrimer growth approaches (DP=2
链接:http://onlinelibrary.wiley.com/doi/10.1002/anie.201706522/abstract