Charge transfer aided selective sensing and capture of picric acid by triphenylbenzenes
Charge transfer aided selective sensing and capture of picric acid by triphenylbenzenes
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DOI：
10.1039/c4nj01093k
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发表时间：
2015-02
影响因子：
3.3
通讯作者：
Pratap Vishnoi;Saumik Sen;G. Patwari;R. Murugavel
中科院分区：
文献类型：
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作者：
Pratap Vishnoi;Saumik Sen;G. Patwari;R. Murugavel
用甲基取代1，3，5-三(4‘-氨基苯基)苯的N-H质子，合成了1，3，5-三(4’-(N，N-二甲氨基)苯基)苯。该化学传感器在苦味酸存在下具有很高的选择性和显著的荧光猝灭，检测下限为1.5ppm。用吸收光谱、荧光发射和核磁共振氢谱技术研究了选择性的来源。1，3，5-三(4‘-(N，N-二甲氨基)苯基)苯及其苦味酸配合物的固态结构表明，1，3，5-三(4’-(N，N-二甲氨基)苯基)苯与苦味酸之间存在多个氢键(N-H⋯O和C-H⋯O)、π-π相互作用和静电相互作用。从苦味酸到1，3，5-三(4‘-(N，N-二甲氨基)苯基)苯的质子转移过程导致苦味酸阴离子的形成和含有二甲基铵(-NHMe2+)基团的三质子化的1，3，5-三(4’-(N，N-二甲氨基)苯基)苯物种。
A fluorescent chemo-sensor, 1,3,5-tris(4′-(N,N-dimethylamino)phenyl)benzene was synthesized by substituting the N–H protons of 1,3,5-tris(4′-aminophenyl)benzene with methyl groups. The chemo-sensor shows highly selective and remarkable fluorescence quenching in the presence of picric acid with a detection limit of 1.5 ppm. The origin of the selectivity was investigated using absorption, fluorescence emission and 1H NMR spectroscopic techniques. The solid state structure of 1,3,5-tris(4′-(N,N-dimethylamino)phenyl)benzene and its picric acid complex reveals multiple hydrogen bonds (N–H⋯O and C–H⋯O), π–π interactions and electrostatic interactions between 1,3,5-tris(4′-(N,N-dimethylamino)phenyl)benzene and picric acid. The proton transfer process from picric acid to 1,3,5-tris(4′-(N,N-dimethylamino)phenyl)benzene results in the formation of picrate anions and the triply protonated 1,3,5-tris(4′-(N,N-dimethylamino)phenyl)benzene species containing dimethylammonium (–NHMe2+) groups.