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Issue 38, 2013
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Template-directed self-assembly by way of molecular recognition at the micellar–solvent interface: modulation of the critical micelle concentration

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Abstract

By incorporating the concepts of structural preorganisation and complementarity in concert with non-covalent donor–acceptor [π⋯π] and hydrophobic interactions, a duo of π-electron deficient bipyridinium-based linear and gemini amphiphiles capable of responding to molecular templation have been designed and synthesised. When combined with π-electron rich di(ethylene glycol)-disubstituted 1,5-dihydroxynaphthalene, a dramatic decrease in the critical aggregation concentration by ≈66% was observed with concomitant increases in the hydrodynamic diameter, ζ-potential, and Langmuir surface pressures of the micellar solutions—thus enhancing the detergents’ efficiency and effectiveness at lowering the surface tension of water. By employing a phase separation model that takes into account the degree of counterion binding to the micellar aggregate superstructure, the effects of donor–acceptor templation on the Gibb's free energy of micellisation (ΔG°M) for the amphiphiles was quantified. It was found that donor–acceptor templation was capable of lowering ΔG°M by up to 1.75 kcal mol−1 at which point it was observed, while under the influence of molecular templation, that linear single hydrophobic tailed detergent molecules exhibit properties characteristic of double-tailed phospholipid-like gemini surfactants.

Graphical abstract: Template-directed self-assembly by way of molecular recognition at the micellar–solvent interface: modulation of the critical micelle concentration

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Publication details

The article was received on 16 Jul 2013, accepted on 08 Aug 2013 and first published on 08 Aug 2013


Article type: Paper
DOI: 10.1039/C3OB41467A
Citation: Org. Biomol. Chem., 2013,11, 6483-6492
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    Template-directed self-assembly by way of molecular recognition at the micellar–solvent interface: modulation of the critical micelle concentration

    M. A. Olson, J. R. Thompson, T. J. Dawson, C. M. Hernandez, M. S. Messina and T. O'Neal, Org. Biomol. Chem., 2013, 11, 6483
    DOI: 10.1039/C3OB41467A

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