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Crystal Engineering Approach To Design Colorimetric Indicator Array To Discriminate Positional Isomers of Aromatic Organic Molecules
Author(s) -
Trivedi Darshak R.,
Fujiki Yuzo,
Fujita Norifumi,
Shinkai Seiji,
Sada Kazuki
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800341
Subject(s) - crystal engineering , synthon , crystal (programming language) , supramolecular chemistry , molecule , structural isomer , chemistry , hydrogen bond , analyte , crystal structure , crystallography , grinding , materials science , stereochemistry , organic chemistry , computer science , programming language , composite material
Discriminating by color : A 2D colorimetric indicator array has been designed by a crystal engineering approach (N⋅⋅⋅HO 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 π 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 N⋅⋅⋅HO 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.