Synthesis and stereochemistry of long-chain quinoxaline metallocyclophanes

Howard, Mark J. and Heirtzler, Fenton R. and Dias, Sandra I. G. (2008) Synthesis and stereochemistry of long-chain quinoxaline metallocyclophanes. Journal of Organic Chemistry, 73 (7). pp. 2548-2553. ISSN 0022-3263. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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Condensation of 1,2-diamino-4,5-bis(n-alkoxy)arenes with an oligopyridyl-type alpha-diketone afforded a series of long-chain pyridine-quinoxaline hybrids. These were evaluated for their ability to self-assemble with tetrahedral Cu(I) and Ag(I) to form dimeric, double-decker amphiphillic complexes having a flattened metallocyclophane topology. Detailed NOESY and T-1 relaxation time experimentation showed that the configuration of the dicoppper (I) complexes corresponds to inversion (meso) symmetry, which leads to an extended molecular shape, wherein the alkoxy chains of the individual ligand components lie on opposite sides of the metallocyclophane core, as opposed to the same side. Preliminary measurements show that the disilver(I) complexes having (C12H25)-C-n and (C18H37)-C-n chains exhibit reversible melting processes and undergo two endothermic transitions each, at 189/237 and 59/80 degrees C, respectively.

Item Type: Article
Uncontrolled keywords: field-effect transistors discotic liquid-crystals organic electronics supramolecular assemblies conjugated systems room-temperature complexes stacking packing organization
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Science Technology and Medical Studies > School of Biosciences > Protein Science Group
Depositing User: Mark Howard
Date Deposited: 11 Mar 2009 15:23
Last Modified: 22 May 2014 14:04
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