3’-(4-溴萘-1-基)[1,1’-联苯基]-4-腈的合成及性能
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摘要
以4-溴苯腈为起始原料经过Suzuki偶联反应、Miyanra硼化反应等合成了3’-(4-溴萘-1-基)[1,1’-联苯基]-4-腈(Ⅲ),利用~1 H NMR、~(13) C NMR对其结构进行了表征.考察了反应温度、膦配体及碱等因素对3-溴-4’-腈基联苯(Ⅰ)收率的影响.结果表明,55℃为最佳反应温度、Pd_2(dba)_3作为催化剂、三(对甲苯基)膦为配体,化合物Ⅰ收率最高,达到92.3%.通过TG、荧光发射光谱研究了化合物Ⅲ的发光效率和稳定性.化合物Ⅲ具有很好的热稳定性,失重5%的温度为321.5℃.
3'-(4-Bromonaphthalene-1-yl)[1,1'-biphenyl]-4-nitrile(Ⅲ)was synthesized by Suzuki reaction and Miyanra reaction using 4-bromobenzonitrile as a raw material.The structure of the compound Ⅲ was characterized by ~1 H NMR and ~(13) C NMR.The effects of reaction temperature,alkali and phosphine ligand on the yield of the compoundⅠ were studied.The results showed that the highest yield of the compoundⅠwas 92.3%with Pd_2(dba)_3 as catastyst and tri(p-tolyl)phosphine as ligand at 55 ℃ of the optimal reaction temperature.Thermal stability properties and optical properties of the compound Ⅲ were determined with TG and fluorescence spectrum.The compoundⅢhad good thermal stability,5% weight loss temperatures was 321.5℃.
3'-(4-Bromonaphthalene-1-yl)[1,1'-biphenyl]-4-nitrile(Ⅲ)was synthesized by Suzuki reaction and Miyanra reaction using 4-bromobenzonitrile as a raw material.The structure of the compound Ⅲ was characterized by ~1 H NMR and ~(13) C NMR.The effects of reaction temperature,alkali and phosphine ligand on the yield of the compoundⅠ were studied.The results showed that the highest yield of the compoundⅠwas 92.3%with Pd_2(dba)_3 as catastyst and tri(p-tolyl)phosphine as ligand at 55 ℃ of the optimal reaction temperature.Thermal stability properties and optical properties of the compound Ⅲ were determined with TG and fluorescence spectrum.The compoundⅢhad good thermal stability,5% weight loss temperatures was 321.5℃.
引文
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[6]赵祥华,黎小胜,王莉敏,等.两种基于吡啶/芴的有机配体的设计、合成、表征及其光学性质[J].信阳师范学院学报(自然科学版),2017,30(2):256-259.ZHAO Xianghua,LI Xiaosheng,WANG Limin,et al.Design,synthesis,characteristics and optical properties of two pyridine/fluorene based organic ligands[J].Journal of Xinyang Normal University(Nature Science Edition)2017,30(2):256-259.
[7]GHOLINEJAD M,HAMED F,BIJI P.A novel polymer containing phosphorus-nitrogen ligands for stabilization of Palladium nanoparticles:an efficient and recyclable catalyst for Suzuki and Sonogashira reactions in neat water[J].Dalton Transactions(Cambridge,England:2003),2015,44(32):14293-14303.
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[9]GHOLINEJAD M,RAZEGHI M,NAJERA C.Magnetic nanoparticles supported oxime palladacycle as a highly efficient and separable catalyst for room temperature Suzuki-Miyaura coupling reaction in aqueous media[J].Rsc Advances,2015,5(61):49568-49576.
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