季戊四醇衍生的咪唑鎓化合物的合成及其对阴离子的光谱响应
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摘要
咪唑鎓本身带有正电荷,2-位碳氢(C2-H)具有一定的酸性,是一种良好的氢键供体,能与阴离子形成氢键。因此,咪唑鎓可以识别各种无机阴离子和生物体内重要的阴离子。本文利用四(1-咪唑甲基)甲烷的独特结构,通过烷基化反应,合成了多咪唑鎓盐2、含有多功能臂的双咪唑鎓盐3和咪唑鎓环番4。采用荧光发射光谱法研究了咪唑鎓盐2、3、4对阴离子(Cl~-、Br~-、I~-、CH_3COO~-、PhCOO~-、HSO_4~-)的光谱响应。结果表明,咪唑鎓盐2和咪唑鎓环番4a加入Cl~-,荧光强度明显增强;咪唑鎓盐3a加入PhCOO~-,荧光强度明显减弱;咪唑鎓盐3b和咪唑鎓环番4b加入I~-,荧光强度明显增强。
The imidazolium group is an attractive building block for anion receptors because in contributes a positive charge and relatively acidic C2-hydrogen. By the use of tetra( 1-imidazolylmethyl) methane 1,we designed a series of novel imidazoliums with alkylating reagents,including imidazolium 2,the open chain bis-imidazolium salt 3,imidazolium cyclophane 4. The spectral response of compound 2,3,4 to anion was further determined by fluorescence spectra. The results showed that imidazolium 2 and imidazolium cyclophane 4 a have a better selectivity for Cl~-,bisimidazolium 3 a has definite recognition ability to PhCOO~-,bisimidazolium 3 b and imidazolium cyclophane 4 b have a better selectivity for I~-.
The imidazolium group is an attractive building block for anion receptors because in contributes a positive charge and relatively acidic C2-hydrogen. By the use of tetra( 1-imidazolylmethyl) methane 1,we designed a series of novel imidazoliums with alkylating reagents,including imidazolium 2,the open chain bis-imidazolium salt 3,imidazolium cyclophane 4. The spectral response of compound 2,3,4 to anion was further determined by fluorescence spectra. The results showed that imidazolium 2 and imidazolium cyclophane 4 a have a better selectivity for Cl~-,bisimidazolium 3 a has definite recognition ability to PhCOO~-,bisimidazolium 3 b and imidazolium cyclophane 4 b have a better selectivity for I~-.
引文
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[3]W W Gao,S Rasheed,V K R Tangadanchu et al.Sci.China Chem.,2017,60(6):769~785.
[4]L Zhang,K V Kumar,S Rasheed et al.Chem.Biol.Drug Design,2015,86(4):648~655.
[5]L Zhang,X M Peng,G L V Damu et al.Med.Res.Rev.,2014,34(2):340~437.
[6]P Rajakumar,R Padmanabhan et al.Tetrahed.Lett.,2010,51:1059~1063.
[7]L Yang,S Qin,X Su et al.Org.Biomol.Chem.,2010,8:339~348.
[8]蒋宗林,肖蓉,苏晓渝等.高等学校化学学报,2003,24(1):64~67.
[9]谢仕伟,蒋宗林,王心良等.西华师范大学学报(自然科学版),2013,34(2):180~183.
[10]Y X Xu,N Y Ye,D J Zhang et al.J.Colloid Interf.Sci.,2017,497:333~342.
[11]Z Li,X H Yu,Y Chen et al.J.Org.Chem.,2017,82(24):13368~13375.
[12]F Liu,P F Hao,T L Yu et al.J.Mol.Struct.,2016,1119:431~436.
[13]J Y C Lim,I Marques,A L.Thompson et al.J.Am.Chem.Soc.,2017,139:3122~3133.
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[15]A Brown,P D Beer.Chem.Commun.,2016,52:8645~8658.