Self-assembly of naphthalene diimides into cylindrical microstructures |
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Authors: | Massimiliano Tomasulo Andrew JP White Françisco M Raymo |
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Institution: | a Center for Supramolecular Science, Department of Chemistry, University of Miami, 1301 Memorial Drive, FL 33146-0431, USA b Department of Chemistry, Imperial College London, South Kensington, London SW7 2AY, UK |
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Abstract: | 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. |
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Keywords: | Bolaamphiphiles Hydrogen bonding Hydrophobic interactions Naphthalene diimides Self-assembly Supramolecular arrays |
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