N-Aryl Pyrrolo-tetrathiafulvalene Based Ligands: Synthesis and Metal Coordination

被引:27
作者
Balandier, Jean-Yves [1 ]
Chas, Marcos [1 ]
Dron, Paul I. [1 ]
Goeb, Sebastien [1 ]
Canevet, David [1 ]
Belyasmine, Ahmed [1 ]
Allain, Magali [1 ]
Salle, Marc [1 ]
机构
[1] Univ Angers, Inst Sci & Technol Mol Angers, MOLTECH ANJOU, UMR CNRS 6200, F-49045 Angers, France
关键词
CONCAVE-CONVEX COMPLEMENTARITY; BUILDING-BLOCKS; SUPRAMOLECULAR CHEMISTRY; MOLECULAR RECOGNITION; FULLERENES; TTF; ASSEMBLIES; COMPLEX; SQUARES; PT(II);
D O I
10.1021/jo902529e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straight forward general synthetic access to N-aryl-1,3-dithiolo[4,5-c]pyrrole-2-thione derivatives 6 from acetylenedicarbaldehyde monoacetal is depicted. In addition to their potentiality as precursors to dithioalkyl-pyrrole derivatives, thiones 6 are key building blocks to N-aryl monopyrrolotetrathiafulvalene (MPTTF) derivatives 10. X-ray structures of four of these thiones intermediates, reminiscent of the corresponding MPTTF derivatives, are provided. When the aryl group is it binding pyridyl unit, the MPTTF derivative 10a can coordinate M(II) salts (M = Pt, Pd). The first examples of metal-directed orthogonal MPTTF-based dimers 11-14, obtained through coordination of 10a to cis-blocked square planar Pt or Pd complexes are described. Studies on the parameters influencing the dimer construction are presented, as well its first recognition properties of the resulting electron-rich clip for C-60.
引用
收藏
页码:1589 / 1599
页数:11
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