Facile and Efficient Catalyst-Free Preparation of Poly(propargyl quinolinium bromide) and Poly(propargyl acridinium bromide) and Characterizations of Their Structures and Properties

doi:10.6023/A13111161

Acta Chimica Sinica ›› 2014, Vol. 72 ›› Issue (1): 35-40.DOI: 10.6023/A13111161 Previous Articles Next Articles

Article

聚溴化炔丙基喹啉及聚溴化炔丙基吖啶的简便高效制备及其结构与性质表征

周常明^a,b, 陈道勇^a,b

a 复旦大学高分子科学系上海 200433;
b 聚合物分子工程国家重点实验室上海 200433

投稿日期:2013-11-16 发布日期:2013-12-17
通讯作者: 陈道勇，E-mail：chendy@fudan.edu.cn；Tel.：+86-21-65643989 E-mail:chendy@fudan.edu.cn
基金资助:
项目受国家自然科学基金（Nos. 91127030，21334001）及科技部973项目基金（No. 2011CB932503）资助.

Facile and Efficient Catalyst-Free Preparation of Poly(propargyl quinolinium bromide) and Poly(propargyl acridinium bromide) and Characterizations of Their Structures and Properties

Zhou Changming^a,b, Chen Daoyong^a,b

a Department of Macromolecular Science, Fudan University, Shanghai 200433;
b State Key Laboratory of Molecular Engineering of Polymer, Shanghai 200433

Received:2013-11-16 Published:2013-12-17
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 91127030 and 21334001) and the Ministry of Science and Technology of China (No. 2011CB932503).

1. Facile and Efficient Catalyst-Free Preparation of Poly(propargyl quinolinium bromide) and Poly(propargyl acridinium bromide) and Characterizations of Their Structures and Properties.PDF(220KB)

Abstract

In this paper, we report facile and efficient preparation of poly(propargyl quinolinium bromide) (PPQB) and poly(propargyl acridinium bromide) (PPAB). Both PPQB and PPAB are conjugated polymers with polyacetylene as backbones. Besides, they are polyelectrolytes since the side groups of PPQB and PPAB are quaternized quinolinium and acridinium, respectively. Therefore, PPQB and PPAB are conjugated polyelectrolytes, which are promising in many important applications. PPQB was prepared by reaction of the mixture of propargyl bromide (PB) and quinoline in DMF at 60 ℃ for 100 h. PPAB was synthesized under the same conditions via the same process except that acridine was used in the place of quinoline. The preparations are very simple and efficient, which need no any catalyst or initiator. The as-prepared PPQB and PPAB were characterized by elemental analysis and GPC-MALLS. Elemental analysis confirmed that PPQB and PPAB were the respective homopolymers of propargyl quinolinium bromide (PQB) and propargyl acridinium bromide (PAB). The molecular weights of the PPQB and PPAB were measured to be 1.8×10⁵ and 8.1×10⁴ g/mol, respectively, indicating efficient polymerizations of the respective monomers PQB and PAB. A tentative mechanism for the polymerizations was proposed as follows: firstly, the tertiary amine group of quinoline or acridine was quaternized by PB, leading to activation of the carbon-carbon triple bonds of the resultant quaternized salt; then, the nucleophilic attack on the triple bonds by pyridine resulted in carbon anions, which initiated the anionic polymerization of the quaternized salt. Furthermore, fluorescent and conductive properties of PPQB and PPAB were studied. Fluorescent measurements revealed that both PPQB and PPAB solutions had relatively strong fluorescent emissions, and the conductivity measurements demonstrated good conductivities of PPQB and PPAB films. Compared with poly(propargyl pyridinium bromide) that we reported previously, PPQB and PPAB are much less hygroscopic when exposed to air, so that PPQB and PPAB films are stable in the air. This broadens the applications of the two polymers.

Key words: polyelectrolyte, mono-substituted polyacetylene, catalyst-free, fluorescence, conductivity

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Zhou Changming, Chen Daoyong. Facile and Efficient Catalyst-Free Preparation of Poly(propargyl quinolinium bromide) and Poly(propargyl acridinium bromide) and Characterizations of Their Structures and Properties[J]. Acta Chimica Sinica, 2014, 72(1): 35-40.

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聚溴化炔丙基喹啉及聚溴化炔丙基吖啶的简便高效制备及其结构与性质表征

Facile and Efficient Catalyst-Free Preparation of Poly(propargyl quinolinium bromide) and Poly(propargyl acridinium bromide) and Characterizations of Their Structures and Properties

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