1033721-75-3Relevant academic research and scientific papers
Synthesis of dicarboxylate "C-clamp" 1,2-diethynylarene compounds as potential transition-metal ion hosts
Reisner, Erwin,Lippard, Stephen J.
, p. 156 - 163 (2008/09/18)
We report an efficient convergent synthesis of a new type of C-clamp ligand with a 1,2-diethynylarene scaffold involving a chelate host capable of binding a guest molecule in its endo-dicarboxylate pocket. The chemistry involves a combination of palladium-catalyzed Sonogashira, Heck, and Suzuki cross-coupling reactions. The compounds 2,3-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl] triptycene and 4,5-bis[2-(2′-carboxybiphenyl-4-yl)ethynyl]veratrole and their 2′-carboxy-m-terphenyl-4-yl analogues were designed as dinucleating ligands to assemble carboxylate-bridged transition-metal complexes with a windmill geometry. The X-ray crystal structure of one such C-clamp compound containing co-crystallized water molecules reveals strong hydrogen bonds of the aqua guest to the endo-oriented carboxylic acid entities of the C-clamp host. In addition, two syn-N-donor ligands were prepared as a synthetic scaffold to mimic the geometric arrangement of N-donor atoms in carboxylate-bridged dinuclear proteins. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
