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首页> 外文期刊>Journal of Applied Polymer Science >Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions
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Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

机译：通过环加成反应合成新型的含萘部分的光敏杂环聚酰亚胺

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1-Naphthylacetic acid (1) was reacted with thionyl chloride and 1-naphthylacetyl chloride (2) was obtained in a quantitative yield. The reaction of this acid chloride (2) with isoeugenol (3) was performed in chloroform and a novel isoeugenol ester derivative (4) as a monomer was obtained in a high yield. The compound (4) was characterized by H-1-NMR, IR, mass, and elemental analyses and then was used for the preparation of a model compound (6) and polymerization reactions. 4-Phenyl-1,2,4-triazoline-3,5-dione (PhTD) (5) was allowed to react with compound (4). The reaction is very fast and gives only one double adduct (6) via Diels-Alder and ene pathways in an excellent yield. The polymerization reactions of the novel monomer (4) with bistriazolinediones [bis-(p-3,5-dioxo-1,2,4-triazolin-4-ylphenyl)methane (7) and 1,6-bis-(3,5-dioxo-1,2,4-triazolin-4-yl)hexane] (8) were carried out in N,N-dimethylacetamide (DMAc) at room temperature. The reactions are exothermic and fast and gave novel heterocyclic polyimides containing a naphthalenic pendant group (9) and (10) via repetitive Diels-Alder-ene polyaddition reactions. Stereochemical analysis of the model compound and fluorimetric studies of the model compound as well as polymers were done conclusively. Excimer formation of the polymers and its effect on fluorescence emission were investigated and some structural characterization and physical properties of these novel heterocyclic polyimides are reported. (C) 2000 John Wiley & Sons, Inc. [References: 15]
机译：使1-萘乙酸（1）与亚硫酰氯反应，以定量收率得到1-萘基乙酰氯（2）。该酰氯（2）与异丁香酚（3）的反应在氯仿中进行，并以高收率获得了作为单体的新型异丁香酚酯衍生物（4）。通过H-1-NMR，IR，质量和元素分析对化合物（4）进行表征，然后将其用于模型化合物（6）的制备和聚合反应。使4-苯基-1,2,4-三唑啉-3,5-二酮（PhTD）（5）与化合物（4）反应。反应非常快，并且通过Diels-Alder和ene途径仅产生一个双加合物（6），收率很高。新型单体（4）与双三唑啉二酮[双-（p-3,5-二氧-1,2,4-三唑啉-4-基苯基）甲烷（7）和1,6-双-（3， [5-二氧-1,2,4-三唑啉-4-基）己烷]（8）在室温下于N，N-二甲基乙酰胺（DMAc）中进行。反应是放热的并且快速的，并且通过重复的Diels-Alder-ene加聚反应得到了含有萘侧基（9）和（10）的新型杂环聚酰亚胺。结论性地进行了模型化合物的立体化学分析和模型化合物以及聚合物的荧光分析。研究了聚合物的准分子形成及其对荧光发射的影响，并报道了这些新型杂环聚酰亚胺的一些结构特征和物理性质。 （C）2000 John Wiley＆Sons，Inc. [参考：15]

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