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E-Journal of Chemistry
Volume 8 (2011), Issue 1, Pages 319-325

Synthesis of Glucose Based Water Soluble Molecular Tweezers as Molecular Recognition Scaffolds

Lalit Sharma

Department of Applied ChemistryShaheed Bhagat Singh College of Engg & Tech., Ferozepur-52 004, India

Received 3 May 2010; Accepted 18 July 2010

Copyright © 2011 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Dry heating of 4,4’-methylenedianiline and N,N’-dimethyl-4,4’-methylenedianiline with 5,6-anhydro-1,2-o-isopropylidene-α-D-glucofuranose afforded molecular tweezers having tertiary amino group linked to C-6 of the glucose moiety. These molecular tweezers on deprotection with dilute acid yielded water soluble analogs which were explored for the solubilization of neutral arenes viz. naphthalene, biphenyl, durene, fluorene, anthracene and phenanthrene in acidic aqueous medium. These solid liquid extraction studies revealed that 6,6’-(N,N’-dimethyl-4’’,4’’’-methylenedianilino) bis (α-D-glucopyranose) causes an approximate 31 fold increase in the solubility of biphenyl in aqueous medium and has best complementarity for naphthalene by forming 1:1 complex.