Combining Orthogonal Chain‐End Deprotections and Thiol–Maleimide Michael Coupling: Engineering Discrete Oligomers by an Iterative Growth Strategy. (27th September 2017)

• Record Type: Journal Article
• Authors: Huang, Zhihao; Zhao, Junfei; Wang, Zimu; Meng, Fanying; Ding, Kunshan; Pan, Xiangqiang; Zhou, Nianchen; Li, Xiaopeng; Zhang, Zhengbiao; Zhu, Xiulin
• Is Part Of: Angewandte Chemie. Volume 129:Number 44(2017)
• Page Start: 13800
• Page End: 13805
• Publication Date: 2017-09-27
• Subjects: Dendrimere -- Diskrete Oligomere -- Iteratives Wachstum -- Michael-Additionen -- Thiol-Maleimid-Kupplung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201706522
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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 2 n −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=2 n −1) or double exponential dendrimer growth approaches (DP=2 2 n −1) with significantly accelerated growth rates. A versatile, efficient, and metal‐free method for construction of discrete oligomers with tailored structures and a high growth rate would greatly facilitate research into the structure–property relationships of sophisticated polymeric materials.