Facile synthesis of end-functionalized regioregular poly(3-alkylthiophene)s via modified Grignard metathesis reaction
Facile synthesis of end-functionalized regioregular poly(3-alkylthiophene)s via modified Grignard metathesis reaction
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DOI：
10.1021/ma051096q
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发表时间：
2005-12-13
期刊：
影响因子：
5.5
通讯作者：
McCullough, RD
中科院分区：
文献类型：
--
作者：
Jeffries-El, M;Sauvé, G;McCullough, RD
提出了一种合成末端官能化的区域规整聚（3-烷基噻吩）的简单方法。利用改进的格氏复分解反应（GRIM），合成了一系列在聚合物的一端或两端带有官能团的聚合物。该方法已被证明与各种不同类型的格氏试剂（即，芳基、烷基、烯丙基、乙烯基等）。这些的反应性取决于它们的性质，其中烯丙基、乙炔基和乙烯基产生单官能化聚合物，并且所有其他基团产生双官能化聚合物。通过MALDI-TOF和H-1 NMR的组合监测聚合物的端基组成，并且在大多数情况下接近100%。通过利用适当的保护基团，-OH、-CHO和-NH 2基团已被结合到聚合物末端上。这种方法的主要优点是，它允许原位官能化的区域规则的聚噻吩，在一个步骤中产生各种封端的聚合物。与先前报道的方法相比，这种方法是有利的，因为它不仅可靠，而且高度通用和高效。
A simple method for the synthesis of end-functionalized regioregular poly(3-alkylthiophene)s is presented. Using a modified Grignard metathesis (GRIM) reaction, a series of polymers have been synthesized bearing functional groups on one or both ends of the polymer. This method has been demonstrated to work with a variety of different types of Grignard reagents (i.e., aryl, alkyl, allyl, vinyl, etc.). The reactivity of these depends on their nature, where allyl, ethynyl, and vinyl groups produced monofunctionalized polymers, and all others yielded difunctionalized polymers. The end group composition of the polymers was monitored by a combination of MALDI-TOF and H-1 NMR and approaches 100% in most cases. By utilizing the proper protecting groups -OH, -CHO, and -NH2 groups have been incorporated onto the polymer ends. The main advantage of this method is that it allows for the in situ functionalization of regioregular polythiophene, generating a variety of end-capped polymers in one step. This approach is advantageous in comparison to previously reported methods because it is not only reliable but also highly versatile and highly efficient.