Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany) http://www.meier-michael.com.
Angew Chem Int Ed Engl. 2014 Jan 13;53(3):711-4. doi: 10.1002/anie.201308960. Epub 2013 Dec 4.
A new strategy to achieve sequence control in polymer chemistry based on the iterative application of the versatile Passerini three-component reaction (P-3CR) in combination with efficient thiol-ene addition reactions is introduced. First, stearic acid was used as a starting substrate to build up a sequence-defined tetramer with a molecular weight of 1.6 kDa. Using an acid-functionalized PEG allowed for an easier isolation of the sequence-defined macromolecules by simple precipitation and led to a sequence-defined pentamer in a block-copolymer architecture. Importantly, this new strategy completely avoids protecting group chemistry. By following this strategy, a different side chain can be introduced to the polymer/oligomer backbone in a simple way and at a defined position within the macromolecule.
介绍了一种基于多功能的 Passerini 三组分反应（P-3CR）的迭代应用以及高效的硫醇-烯加成反应在聚合物化学中实现序列控制的新策略。首先，使用硬脂酸作为起始底物，构建了分子量为 1.6 kDa 的序列限定的四聚体。使用酸官能化的 PEG 可以通过简单的沉淀更容易地分离序列限定的大分子，并得到具有嵌段共聚物结构的序列限定的五聚体。重要的是，这种新策略完全避免了保护基团化学。通过采用这种策略，可以在聚合物/低聚物主链上以简单的方式和在大分子中的特定位置引入不同的侧链。
