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Aromatic polyesters derived from 5,5′-disubstituted bis(m-phenylene) crown ethers
Polymer ( IF 4.6 ) Pub Date : 2018-03-20 , DOI: 10.1016/j.polymer.2018.03.031
Harry W. Gibson , Devdatt S. Nagvekar , Norimitsu Yamaguchi , Yadollah Delaviz , Jason W. Jones , Peter Balanda , Abaneshwar Prasad , Herve’ Marand

A new monomer of the AB type, 5-carboxy-1,3-phenylene-5′-hydroxy-1′,3′-phenylene-32-crown-10 (5), was synthesized. Direct polymerizations of bis(5-hydroxy-1,3-phenylene)-32-crown-10 (13), an AA diphenolic macrocyclic monomer, with BB diacid monomer bis(5-carboxy-1,3-phenylene)-26-crown-8 (14) and its larger analog bis(5-carboxy-1,3-phenylene)-32-crown-10 (16) were accomplished via the Higashi method. The resultant polyesters 15 and 17, which both contain two macrocycles per repeat unit, were soluble in common organic solvents such as chloroform and tetrahydrofuran, amorphous in nature and possessed high thermal stability (5% weight loss > 370 °C in air). Main chain poly(ester crown ether)s 18 and 19 based on bis(5-carboxy-1,3-phenylene)-32-crown-10 (16), and hydroquinone (HQ) and biphenol (BP), respectively, were synthesized; these two polyesters also possess high thermal stability (5% weight loss > 386 °C in air) and are amorphous. These polymacrocycles are suitable polytopic hosts for complexation with 4,4′-bipyridinium derivatives, as demonstrated by the binding of paraquat diol (21a) by polyester 20 with Ka = 2.0 (±0.7) x 102 M−1 (23 °C, 4:6 w:w CD3CN:CDCl3). Threading of the cyclic units in these polyesters by linear polymers such as polystyrene and PMMA leads to compatiblized blends via polypseudorotaxane formation; this methodology represents a new approach to compatibilization.



中文翻译:

衍生自5,5'-二取代的双(亚苯基)冠醚的芳族聚酯

合成了AB型的新单体5-羧基-1,3-亚苯基-5'-羟基-1',3'-亚苯基-32-皇冠-10(5)。双(5-羟基-1,3-亚苯基)-32-crown-10(13)(AA双酚大环单体)与BB二酸单体双(5-羧基-1,3-亚苯基)-26-的直接聚合冠8(14)及其较大的类似物双(5-羧基-1,3-亚苯基)-32-冠-10(16)是通过Higashi方法完成的。所得聚酯1517,每个重复单元均包含两个大环,可溶于常见的有机溶剂,如氯仿和四氢呋喃,本质上是无定形的,并具有很高的热稳定性(在空气中5%重量损失> 370°C)。分别是基于双(5-羧基-1,3-亚苯基)-32-皇冠-10(16)和对苯二酚(HQ)和双酚(BP)的主链聚(酯冠醚)1819合成 这两种聚酯还具有很高的热稳定性(在空气中5%重量损失> 386°C),并且是无定形的。这些多环大环化合物是适合与4,4'-联吡啶鎓衍生物络合的多羟基化合物主体,正如聚酯20与百草枯二醇(21a)与K a的结合所证明的那样。 = 2.0(±0.7)x 10 2  M -1(23°C,4:6 w:w CD 3 CN:CDCl 3)。这些聚酯中的环状单元被线型聚合物(例如聚苯乙烯和PMMA)穿入,会通过聚伪轮烷的形成而形成相容的共混物。这种方法代表了一种新的增容方法。

更新日期:2018-03-20
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