对硝基苯胺接枝1,8-萘酰亚胺聚磷腈合成及表征
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摘要
为研究对硝基苯胺接枝1,8-萘酰亚胺聚磷腈的合成工艺,根据亲核取代机理将1,8-萘酰亚胺接枝到聚磷腈上,再根据偶合原理将合成的1,8-萘酰亚胺聚磷腈与对硝基苯胺偶合;偶合过程采用微波法合成,通过计算考察产物的产率,根据产率确定合成工艺条件;并对产物进行结构表征,结果表明350~360 nm之间出现了硝基苯与偶氮双键共轭的紫外光谱吸收峰;在1 594 cm-1处出现偶氮基团-N=N-的红外吸收峰,在1 349 cm-1出现-NO2的红外吸收峰;在1 143 cm-1出现C-N的红外吸收峰.表征结果说明,对硝基苯胺接枝1,8-萘酰亚胺聚磷腈的成功合成.荧光光谱分别产生三处荧光激发和三处荧光发射光谱,说明所合成的产物可作为一种具有应用价值的发光高分子功能材料.
The aim of this study is to research the process of paranitroaniline grafting 1,8- naphthalene imide synthesis. The nucleophilic replace mechanism of 1,8- naphthalene imide grafted on to polyphosphazene is examined,and the principle of Nitroaniline coupled with 1,8- naphthalimide polyphosphazene is outlined. The idea of microwave method of measurement is to analyze the synthetic conditions of coupling process by calculating the productivity. The ultraviolet spectrum results show that conjugated double bond absorption peaks of the nitrobenzene and azo in 350- 360 nm. Infrared spectrum results show that vibration absorption peak of —N = N—azo groups in 1594 cm- 1,the absorption peak of —NO2in 1594 cm- 1and the absorption peak of C—N in 1143 cm- 1. The results shows that paranitroaniline grafted 1,8- naphthalene imide polyphosphazenes. We thus conclude that synthetic product can be used as a kind of valuable light- emitting polymer functional materials based on the fluorescence spectrum results.
The aim of this study is to research the process of paranitroaniline grafting 1,8- naphthalene imide synthesis. The nucleophilic replace mechanism of 1,8- naphthalene imide grafted on to polyphosphazene is examined,and the principle of Nitroaniline coupled with 1,8- naphthalimide polyphosphazene is outlined. The idea of microwave method of measurement is to analyze the synthetic conditions of coupling process by calculating the productivity. The ultraviolet spectrum results show that conjugated double bond absorption peaks of the nitrobenzene and azo in 350- 360 nm. Infrared spectrum results show that vibration absorption peak of —N = N—azo groups in 1594 cm- 1,the absorption peak of —NO2in 1594 cm- 1and the absorption peak of C—N in 1143 cm- 1. The results shows that paranitroaniline grafted 1,8- naphthalene imide polyphosphazenes. We thus conclude that synthetic product can be used as a kind of valuable light- emitting polymer functional materials based on the fluorescence spectrum results.
引文
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[3]张新孟,王秀峰,江红涛,等.聚磷腈功能高分子材料的合成及应用研究进展[J].化工新型材料,2010,11(38):27-29.
[4]王志锋,曹继平,姚楠,等.芳氧基聚磷腈的合成及性能[J].火炸药学报,2010,33(2):61-63.
[5]张文龙,姜文影,赵春山,等.1,8-萘酰亚胺接枝聚磷腈合成工艺研究[J].塑料助剂,2013(3):21-25.
[6]ALLCOCK H R,RAVIKIRAN R,OLSHAVSKY M A.Synthesisof High Polymeric Alkoxy and Aryloxyphosphonitriles.Journal of the American Chemical Society,1965,87(18):4216-4217.
[7]张文龙,赵成龙.聚磷腈接枝官能团的光电性能[J].功能材料,2013,43(24):30-34.
[8]张宏伟,李爱元,沈培康.聚磷腈的研究进展[J].材料导报,2010,7(24):133-135.
[9]URSULA D,BRIGITTE S.Polyphosphazenes with Pyridyl/Alkyl/Amino Gro-ups:Synthesis,Thermal Properties,Ion Uptake and Selectivity[J].Journal of Inorganic and Organometallic Polymers and Materials,2006,16(12):295-306.
[10]黄小彬,尹林,唐小真.一种新型有机无机杂化聚磷腈高分子的制备及表征[J].中国科学,2008,30(1):43-44.
[11]王辉,冯燕,陈杨洋,等.新型对称双偶氮苯化合物的合成及光学性能[J].应用化工,2012,41(9):1493-1496.
[12]李岩.1,8-萘酰亚胺及其衍生物的光谱性质的理论研究[J].吉林化工学院学报,2012,1(29):42-45.
[13]CHANG S,UTECHT R E,LEWIS D E.Synthesis and Bromination of 4-Alkylamino-N-Alkyl-1,8-Naphthalimide[J].Dyes and Pigments,1999,43:83-94.
[14]FAN Shengfa,LUO Duanbin.Nonlinear Refraction in Photo-induced Anisortropic States of Azo-dyes Containing Materilas[J].Optik,2011,122(12):142-144.
[15]乔思怡.含偶氮类聚磷腈非线性材料的合成与表征[D].哈尔滨:哈尔滨理工大学,2012:33-35.
[16]张丽,杨正,姜治伟.含咔唑生色团的聚磷腈的合成与表征[J].功能高分子学报,2005,12:630-634.
[17]REN Jun,ZHAO Xueli,WANG Qiaochun,et al.Synthesis and Fluorescence Properties of Novel Naphthalimide Dimers[J].Dyes and Pigments,2005(64):79-186.
[18]FAN Shengfa,LUO Duanbin.Nonlinear Refraction in Photoinduced Anisortropic States of Azodyes containing Materilas[J].Optik,2011,122(12):142-144.
[19]姜文影.聚磷腈衍生物制备及光电性能研究[D].哈尔滨:哈尔滨理工大学,2013:30-32.
[20]宋桂霞.聚磷腈衍生物的制备及光电导性能的研究[D].哈尔滨:哈尔滨理工大学,2011:36-37.