双(1H苯并咪唑2基)甲烷的合成及其荧光性能研究
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摘要
以邻苯二胺和丙二酸为主要原料,3 mol·L-1盐酸水溶液为反应介质,合成了双(1H-苯并咪唑-2-基)甲烷。采用元素分析、FT-IR、UV-Vis和1H NMR对产物进行了结构表征和确认,并对产物的溶液荧光性能和固体荧光性能进行了测试研究。结果表明,产物在DMF、DMSO和Et OH三种溶剂中均具有315 nm和360 nm附近较强的紫外吸收峰,具有良好的抗日光UVA和UVB紫外线性能。溶液荧光测试表明,产物具有λmax,em=476~483 nm的蓝绿色荧光发射,且溶液荧光具有AIE效应。固体荧光测试发现产物的最大激发波长λmax,ex=252 nm,具有λmax,em=537 nm的黄绿色荧光发射。
The bis(1H-benzimidazol-2-yl) methane was synthesized in 3 mol·L-1HCl solution by using o-phenylenediamine and malonic acid as main raw materials. The target compound was characterized by means of elemental analysis,FT-IR,UV-vis and1 H NMR spectra. UV-Vis,solution fluorescence and solid fluorescence spectroscopy were used to study its photophysics properties. The results show that the compound has two UV absorption peaks at 315 nm and 360 nm in DMSO,DMF and Et OH(1×10-5mol·L-1),and possesses good performance on absorbing sunlight ultraviolet(UVA and UVB). The blue-green fluorescence emission(λmax,em=476-483nm) can be obtained under the excitation wavelength 320 nm in the above three solvents. Besides,a significant AIE effect of the titled compound is found through solution fluorescence tests with different VolDMSO∶VolDCM. Solid fluorescence indicates that the product has strong yellow-green fluorescence emission(λmax,em=537 nm) with the excitation wavelength at 252 nm.
The bis(1H-benzimidazol-2-yl) methane was synthesized in 3 mol·L-1HCl solution by using o-phenylenediamine and malonic acid as main raw materials. The target compound was characterized by means of elemental analysis,FT-IR,UV-vis and1 H NMR spectra. UV-Vis,solution fluorescence and solid fluorescence spectroscopy were used to study its photophysics properties. The results show that the compound has two UV absorption peaks at 315 nm and 360 nm in DMSO,DMF and Et OH(1×10-5mol·L-1),and possesses good performance on absorbing sunlight ultraviolet(UVA and UVB). The blue-green fluorescence emission(λmax,em=476-483nm) can be obtained under the excitation wavelength 320 nm in the above three solvents. Besides,a significant AIE effect of the titled compound is found through solution fluorescence tests with different VolDMSO∶VolDCM. Solid fluorescence indicates that the product has strong yellow-green fluorescence emission(λmax,em=537 nm) with the excitation wavelength at 252 nm.
引文
[1]李焱,马会强,王玉炉.苯并咪唑及其衍生物合成与应用研究进展[J].有机化学,2008,28(2):210-217.
[2]庄俊涛,钱永,吴磊,等.三种双苯并咪唑型荧光增白剂的合成及荧光性能研究[J].应用化工,2011,40(12):2076-2079.
[3]BAI Yubin,ZHANG Anling,TANG Jiangjiang,et al.Synthesis and antifungal activity of 2-chloromethyl-1H-benzimidazole derivatives against phytopathogenic fungi in vitro[J].Journal of Agricultural and Food Chemistry,2013,61(11):2789-2795.
[4]翟文杰,马腾,乔鹏伟,等.苯并咪唑阳离子缩醛型表面活性剂的合成及性能[J].精细化工,2010,27(11):1060-1063.
[5]高阳,陈洪龄,陈步荣,等.盐酸溶液中N-烷基苯并咪唑阳离子对碳钢的缓蚀性能[J].材料保护,2009,42(7):1-3.
[6]张海,林原斌,陈珍娥,等.聚苯并咪唑树脂的合成与性能[J].材料科学与工程学报,2011,29(1):122-127.
[7]金宁人,刘琛,肖庆军,等.高纯度2-(4-氨基苯基)-1H-苯并咪唑-5-胺的合成[J].化工进展,2009,28(5):847-851,863.
[8]张蓉,李锦堂,傅翠梨,等.苯并咪唑类光电功能配合物的研究进展[J].材料导报(综述篇),2011,25(7):61-64,94.
[9]孟江平,耿蓉霞,周成合,等.苯并咪唑类药物研究进展[J].中国新药杂志,2009,18(16):1505-1514.
[10]潘文龙,许炎妹,李超,等.1,1-二(2-苯并咪唑基)-2-苯基乙烯衍生物荧光受体的合成与阳离子识别[J].分析测试学报,2007,26(2):160-164.
[11]潘会宾,高霞.双(2-苯并咪唑基)烷烃的合成和应用研究进展[J].长春师范大学学报(自然科学版),2014,33(4):64-70.
[12]YAO Hongchang,LI Miaomiao,YANG Gaosheng,et al.Ketonization of methylene of bis(benzimidazol-2-yl)methane by molecular oxygen under the catalysis of cobalt(II)ion[J].Inorganica Chimica Acta,2007,360:3959-3964.
[2]庄俊涛,钱永,吴磊,等.三种双苯并咪唑型荧光增白剂的合成及荧光性能研究[J].应用化工,2011,40(12):2076-2079.
[3]BAI Yubin,ZHANG Anling,TANG Jiangjiang,et al.Synthesis and antifungal activity of 2-chloromethyl-1H-benzimidazole derivatives against phytopathogenic fungi in vitro[J].Journal of Agricultural and Food Chemistry,2013,61(11):2789-2795.
[4]翟文杰,马腾,乔鹏伟,等.苯并咪唑阳离子缩醛型表面活性剂的合成及性能[J].精细化工,2010,27(11):1060-1063.
[5]高阳,陈洪龄,陈步荣,等.盐酸溶液中N-烷基苯并咪唑阳离子对碳钢的缓蚀性能[J].材料保护,2009,42(7):1-3.
[6]张海,林原斌,陈珍娥,等.聚苯并咪唑树脂的合成与性能[J].材料科学与工程学报,2011,29(1):122-127.
[7]金宁人,刘琛,肖庆军,等.高纯度2-(4-氨基苯基)-1H-苯并咪唑-5-胺的合成[J].化工进展,2009,28(5):847-851,863.
[8]张蓉,李锦堂,傅翠梨,等.苯并咪唑类光电功能配合物的研究进展[J].材料导报(综述篇),2011,25(7):61-64,94.
[9]孟江平,耿蓉霞,周成合,等.苯并咪唑类药物研究进展[J].中国新药杂志,2009,18(16):1505-1514.
[10]潘文龙,许炎妹,李超,等.1,1-二(2-苯并咪唑基)-2-苯基乙烯衍生物荧光受体的合成与阳离子识别[J].分析测试学报,2007,26(2):160-164.
[11]潘会宾,高霞.双(2-苯并咪唑基)烷烃的合成和应用研究进展[J].长春师范大学学报(自然科学版),2014,33(4):64-70.
[12]YAO Hongchang,LI Miaomiao,YANG Gaosheng,et al.Ketonization of methylene of bis(benzimidazol-2-yl)methane by molecular oxygen under the catalysis of cobalt(II)ion[J].Inorganica Chimica Acta,2007,360:3959-3964.