Crystal engineering approach to design colorimetric indicator array to discriminate positional isomers of aromatic organic molecules.

Crystal engineering approach to design colorimetric indicator array to discriminate positional isomers of aromatic organic molecules.
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DOI:
10.1002/asia.200800341
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发表时间:
2009-02
期刊:
Chemistry, an Asian journal
影响因子:
--
通讯作者:
Darshak R. Trivedi;Yuzo Fujiki;Norifumi Fujita;S. Shinkai;K. Sada
Darshak R. Trivedi;Yuzo Fujiki;Norifumi Fujita;S. Shinkai;K. Sada
中科院分区:
其他
文献类型:
--
作者:
Darshak R. Trivedi;Yuzo Fujiki;Norifumi Fujita;S. Shinkai;K. Sada

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颜色识别:利用固态共研磨的晶体工程方法(NH-O氢键和电荷转移络合)设计了二维比色指示剂阵列,用于直观地识别二羟基萘的位置异构体。通过单晶X射线分析确定了控制pi面紧密堆积的因素,从而确定了络合物的颜色,从而允许通过晶体工程进行微调。采用固态共研磨和电荷转移络合相结合的晶体工程概念,设计了一种识别二羟基萘同分异构体的二维比色指示剂阵列。在所有报道的CT络合物的单晶X射线结构中,都观察到了探针的吡啶N原子与分析物的羟基之间的NH-O超分子合成子。与芳香固体的固态共研磨很容易提供所需的高浓度无溶剂条件,以促进具有更明亮颜色变化的电荷转移络合物的形成。探针D(N,N‘-双(4-吡啶基)均苯四甲酸二亚胺)对8种不同颜色的二羟基萘的CT络合物有很好的分辨能力。
Discriminating by color: A 2D colorimetric indicator array has been designed by a crystal engineering approach (NH-O hydrogen bonding and charge-transfer complexation) involving solid-state co-grinding for the visual discrimination of positional isomers of dihydroxynaphthalene. Factors governing the close packing of pi planes, and hence color of the complex, were determined by single-crystal X-ray analysis, allowing fine tuning by crystal engineering. A 2D colorimetric indicator array to discriminate isomers of dihydroxynaphthalene has been designed by using a crystal engineering concept combined with solid-state co-grinding and charge-transfer complexation. The NH-O supramolecular synthon between the pyridyl N atom of the probe and hydroxy group of the analyte has been observed in all reported single-crystal X-ray structures of resultant CT complexes. Solid-state co-grinding with aromatic solids easily provided the highly concentrated solvent-free conditions required to promote the formation of charge-transfer complexes with brighter color changes. Probe D (N,N'-bis-(4-pyridyl)pyromellitic diimide) showed an excellent ability to discriminate eight isomers of dihydroxynaphthalene with a wide variety of colors of the resultant CT complexes.