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High-Molecular-Weight Poly[2]catenanes Prepared by Hydroxyl-Alkyne Click Chemistry
Macromolecules ( IF 5.5 ) Pub Date : 2024-04-10 , DOI: 10.1021/acs.macromol.4c00431
Jinsa Li 1 , Rui Hu 1 , Ziqing Hu 1 , Shaoyu Xu 1 , Ao Yu 1 , Xiaofan Ji 1
Affiliation  

Due to the combination of flexibility and mobility, polycatenanes have the potential in constructing various functional materials. To date, most of the previous works have reported poly[2]catenanes with a degree of polymerization (DP) of around 20. However, it remains a significant challenge to synthesize poly[2]catenanes with a higher DP value. Hydroxyl–yne click polymerization, bearing the merits of obtaining polymers with high DP values, short reaction time, and mild condition, is promising to be employed in preparing poly[2]catenanes with high DP values. Herein, a strategy using hydroxyl–yne click chemistry to fabricate poly[2]catenanes was proposed. With two hydroxyl groups on both the rings, [2]catenane monomer M1 was prepared. Meanwhile, hexaethylene glycol was alkyne functionalized as M2. With bicyclo[2.2.2]-1,4-diazaoctane (DABCO) catalyzing, M1 and M2 reacted via a hydroxyl–yne click reaction at room temperature. The DP of resultant poly[2]catenane reached up to 36. In addition, tetraphenylethylene (TPE) was modified with propiolic acid to obtain M3. Then, poly([2]catenane-alt-TPE) with aggregation-induced emission (AIE) properties was obtained via the polymerization between M1 and M3 as well.

中文翻译:

羟基-炔点击化学制备高分子量聚[2]环烷

由于柔韧性和流动性的结合,聚链烷具有构建各种功能材料的潜力。迄今为止,大多数先前的工作报道了聚合度(DP)在20左右的聚[2]卡烷。然而,合成具有更高DP值的聚[2]卡烷仍然是一个重大挑战。羟基-炔点击聚合具有获得高DP值聚合物、反应时间短、条件温和等优点,有望用于制备高DP值聚[2]环烷。在此,提出了一种利用羟基-炔点击化学来制造聚[2]环烷的策略。两个环上都有两个羟基,制备[2]链烯单体M1 。同时,六乙二醇被炔烃官能化为M2。在双环[2.2.2]-1,4-二氮杂辛烷(DABCO)催化下,M1M2在室温下通过羟基-炔点击反应发生反应。所得聚[2]链烯的DP达到36。另外,用丙炔酸对四苯乙烯(TPE)进行改性,得到M3。然后,通过M1M3之间的聚合获得了具有聚集诱导发光(AIE)特性的聚([2]catenane- alt -TPE) 。
更新日期:2024-04-10
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