摘要
以4,4'-二溴联苯和苯胺为原料,经钯催化氨基化反应制得N,N'-二苯基联苯胺(1);以1为单体,分别与对二溴苯(2a),4,4'-二溴二苯砜(2b)和4,4'-二溴二苯甲酮(2c)通过钯催化的C-N交叉偶联反应,合成了3个新型的联苯基三苯胺聚合物:联苯基三苯胺苯(3a,收率88%),联苯基三苯胺砜(3b,收率94%)和联苯基三苯胺酮(3c,收率91%),其结构经1H NMR,IR和XRD表征。采用UV-Vis,TG,DSC,荧光光谱和循环伏安法对3a^3c的性能进行了研究。结果表明:3a^3c失重5%的温度分别为479℃,482℃和355℃;玻璃化转变温度分别为199℃,248℃和215℃;λmax分别位于354 nm,359 nm和385 nm;λem分别为489 nm,472 nm和518 nm;EHOMO值分别为-3.96 eV,-3.89 eV,-3.94 eV;ELUMO值分别为-1.16 eV,-1.17 eV和-1.39 eV。
N,N＇-diphenylbenzidine （1） was obtained by palladium-catalyzed C-N cross-coupling reaction of 4,4＇-dibromobiphenyl and aniline.Three novel poly （triphenylamine biphenyl）s,poly （triphenylamine biphenyl） benzene（3a,88%）,poly（triphenylamine biphenyl） sulfone（3b,94%） and poly（triphenylamine biphenyl） ketone （3c,91%） were synthesized by palladium-catalyzed C-N cross-coupling reaction of 1 with p-dibromobenzene （2a）,4,4＇-dibromodiphenylsulfone （2b） and 4,4＇-dibromodiphenylketone（2c）,respectively.The structures were characterized by 1H NMR,IR and XRD.Their properties were investigated by UV-Vis,TG,DSC,fluorescence spectra and electrochemical cyclic voltammetry.The properties of 3a ～ 3c were as follows：5% weight loss temperature were 479 ℃,482 ℃ and 355 ℃,Tg were 199 ℃,248 ℃ and 215 ℃,λmax were 354 nm,359 nm and 385 rnm,λem Were 489 nm,472 nm and 518 nm,EHoMo were-3.96 eV,-3.89 eV,and-3.94 eV,ELUMO were-1.16 eV,-1.17 eV and-1.39 eV,respectively.
出处
《合成化学》
CAS
CSCD
北大核心
2014年第2期139-143,共5页
Chinese Journal of Synthetic Chemistry
基金
山东省自然科学基金资助项目(ZR2011EMM006)
青岛市自然科学基金资助项目[12-1-4-3-(14)-jch]
中国工程物理研究院科技发展基金资助项目(2012A0302015
2012B0302050)
关键词
钯催化C-N交叉偶联反应
联苯基
三芳胺
合成
性能
palladium-catalyzed C-N cross-coupling reaction
biphenyl
triarylamine
synthesis
performance
