Metal-Induced Thiophene Ring Opening and C-C Bond Formation To Produce Unique Hexa-1,3,5-trienediyl-Coupled Non-Innocent Ligand Chelates

Chemistry. 2015 Oct 19;21(43):15163-6. doi: 10.1002/chem.201502748. Epub 2015 Sep 4.

Abstract

Ring opening of thiophenes containing an azo function in 2-position and subsequent dimerization through C-C coupling were observed on reaction with [Ru(acac)2 (CH3 CN)2 ] (acac=acetylacetonate) to produce two 1,3,5-hexatriene-linked redox-active azothiocarbonyl chelate systems. Interaction of the non-innocent chelate ligands and of the metals at a nanoscale distance of 1.45 nm via the conjugated hexatriene bridge was studied by magnetic and electron spectroscopic measurements in conjunction with DFT calculations, revealing four-center magnetic interactions of this unique setting and weak intervalence coupling after reduction.

Keywords: mixed valence; non-innocent ligand; ruthenium; spin coupling; thiophene.