Pal Tuhin Subhra, Mondal Prantik, Kundu Niloy, Chakraborty Swadhin, Ganguly Debabrata, Singha Nikhil K
Rubber Technology Center, Indian Institute of Technology, Kharagpur, 721302, India.
Present address, Department of Chemistry and Biochemistry, University of California, La Jolla, San Diego, California, 92093, USA.
Chemistry. 2024 Mar 20;30(17):e202303367. doi: 10.1002/chem.202303367. Epub 2024 Jan 31.
Polymers with furan functionality have been the subject of extensive research on developing sustainable materials applying a limited number of dynamic covalent approaches. Herein, we introduce a facile, dynamic non-covalent approach to make a furan polymer readily accessible for self-healing applications based on its electrophilic substitution (ES) with a commercially available 1,2,4-triazoline-3,5-dione (TAD) derivative, 4-phenyl-TAD (PTAD). A tailor-made furan polymer, poly(furfuryl methacrylate) (PFMA), considering it an initial illustrative example, was rapidly ES modified with PTAD to produce furfuryl-tagged triazolidine that subsequently associated via inter-molecular hydrogen (H-) bonding to produce a thermally reversible supramolecular polymer network under ambient conditions. The H-bonded network was experimentally quantified via ATR-IR analysis and theoretically rationalized via the density functional theory (DFT) study using smaller organic model compounds analogous to the macromolecular system. Thermoreversible feature of the H-bonded triazolidine-derived supramolecular polymer network enabled the solution reprocessing and self-healing of the polymer material.
具有呋喃官能团的聚合物一直是利用有限数量的动态共价方法开发可持续材料的广泛研究主题。在此，我们介绍一种简便的动态非共价方法，基于市售的1,2,4 - 三唑啉 - 3,5 - 二酮（TAD）衍生物4 - 苯基 - TAD（PTAD）对呋喃聚合物进行亲电取代（ES），从而使其易于用于自修复应用。作为一个初始的示例，一种定制的呋喃聚合物聚（甲基丙烯酸糠酯）（PFMA）与PTAD进行快速ES修饰，生成带有糠基标签的三唑烷，随后通过分子间氢键结合，在环境条件下形成热可逆的超分子聚合物网络。通过ATR - IR分析对氢键网络进行了实验量化，并使用与大分子体系类似的较小有机模型化合物，通过密度泛函理论（DFT）研究从理论上进行了合理化解释。氢键连接的三唑烷衍生超分子聚合物网络的热可逆特性实现了聚合物材料的溶液再加工和自修复。
