Journal
TETRAHEDRON LETTERS
Volume 46, Issue 34, Pages 5695-5698Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.06.086
Keywords
bolaamphiphiles; hydrogen bonding; hydrophobic interactions; naphthalene diimides; self-assembly; supramolecular arrays
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We have designed two rod-shaped compounds each incorporating a naphthalene diimide core and two terminal carboxylic acids. Both molecules aggregate in aqueous solution and spontaneously organize into cylindrical microstructures on the surface of solid substrates. Presumably, hydrogen bonds between the carboxylic acid termini and hydrophobic contacts between the naphthalene diimide cores are mainly responsible for the formation of these supramolecular arrays. Indeed, extended stacks of molecules self-assemble with close contacts between their aromatic cores in single crystals grown from polar solvents. (c) 2005 Elsevier Ltd. All rights reserved.
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