A CPK drawing of our 9-10-9 "arborols" self-assembling into a rod-like, nanoscale architecture. These unique molecules were prepared by reaction of 1,10-bis(bromo)decane with 2 equivalents of the Na salt of triethyl methanetricarboxylate to give the hexaester followed by treatment with "Tris" (trishydroxymethylaminomethane). The result is a 10 carbon alkyl chain with two spherical end groups each possessing 9 hydroxy groups - thus the 9-10-9 designation. The propensity to self-assemble in water producing a thermally reversible gel arises from the lipophilic interactions of the central 10 carbon alkyl chains in adjacent molecules along with the strong tendency of the hydrophilic hydroxyl end groups to H-bond. Numerous 9-n-9 and 6-n-6 series have also been prepared and shown to form analogous gels. Stacked aggregates for the 9-10-9 series were shown, via electron micrographs, to possess rod diameters of 34 to 36 Å and lengths up to 2000 Å. The observed diameters correspond well with the calculated expanded arborol length of 29 Å.
© 2011 Center for Molecular Design and Recognition
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