Lamellar Organic Thin Films through Self-Assembly and Molecular Recognition

Molecular clips possessing U-shaped cavities have been functionalized on their convex side with long aliphatic tails. These molecules form dimers which self-assemble into malleable lamellar thin films. Upon addition of a guest (methyl 3,5-dihydroxybenzoate), a 1:1 host−guest complex is formed, which...

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Published in:Journal of organic chemistry 2001-01, Vol.66 (2), p.391-399
Main Authors: Holder, Simon J, Elemans, Johannes A. A. W, Donners, Jack J. J. M, Boerakker, Mark J, de Gelder, René, Barberá, Joaquín, Rowan, Alan E, Nolte, Roeland J. M
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cited_by cdi_FETCH-LOGICAL-a450t-16ddb1473fbecebade7373416fbcf45f709117d079fe4c83e8ebb00bc04f4fcf3
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container_end_page 399
container_issue 2
container_start_page 391
container_title Journal of organic chemistry
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creator Holder, Simon J
Elemans, Johannes A. A. W
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Nolte, Roeland J. M
description Molecular clips possessing U-shaped cavities have been functionalized on their convex side with long aliphatic tails. These molecules form dimers which self-assemble into malleable lamellar thin films. Upon addition of a guest (methyl 3,5-dihydroxybenzoate), a 1:1 host−guest complex is formed, which prohibits clip dimerization. As a result, the lamellar structure of the material is lost. Complexation of 3,5-dihydroxybenzoic acid in the clip results in host−guest complexes which dimerize by hydrogen bonding interactions between the carboxylic acid functions of the bound guests. This dimerization restores the lamellar type architecture of the material.
doi_str_mv 10.1021/jo0008035
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title Lamellar Organic Thin Films through Self-Assembly and Molecular Recognition
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