meso-Dithiole and tetrathiafulvalene dipyrromethanes a route to metal dithiole–dipyrrin complexes and to fluorescent tetrathiafulvalene–BODIPY

• Published in: Tetrahedron Vol. 67; no. 45; pp. 8740 - 8746
• Main Authors: Huang, Kai-Ling, Bellec, Nathalie, Guerro, Michel, Camerel, Franck, Roisnel, Thierry, Lorcy, Dominique
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.11.2011; Elsevier
• Subjects: BODIPY; Boron; Chemistry; Chemistry, Organic; Coordination compounds; Copper; Dipyrrins; Dipyrromethanes; Electroactive ligands; Exact sciences and technology; Fluorescence; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with only one n hetero atom and condensed derivatives; Miscellaneous; Molecular structure; Nickel; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Strategy; Tetrahedrons; Tetrathiafulvalene; Dipyrromethanes; Dipyrrins; BODIPY; Tetrathiafulvalene; Electroactive ligands; RECOGNITION; BUILDING-BLOCKS; TRIAD; PORPHYRIN; TTF DERIVATIVES; LIGANDS; CHEMISTRY; SYSTEMS; BEARING; UNITS; Boron Complexes; Molecular structure; Nitrogen heterocycle; Ligand; Pyrrole derivatives; Amine borane; Optical properties; Oxidation; Copper; Chemical synthesis; Boron complex; Metal complex; Tetrathiafulvalene derivatives; Transition metal; Acid catalysis; Aldehyde; Zinc; Metal Complexes; Sulfur heterocycle; Nickel; Nitrogen boron heterocycle; Fluorescent compound; Chelates
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.09.019

A series of meso-dithiole and tetrathiafulvalene (TTF) dipyrromethanes have been prepared via the reaction of the appropriate aldehyde with either pyrrole or 3-ethyl-2,4-dimethyl-pyrrole under acid catalysis. Oxidation to the corresponding meso-dithiole dipyrrins is reported together with the formation of the metal chelate complexes (M=Zn, Cu, Ni) as well as the meso-dithiole boron-dipyrromethene (BODIPY). The molecular structures of these metal (Cu, Ni) and boron complexes are presented and discussed. According to a similar strategy the meso-TTF BODIPY is prepared and its photophysical properties are presented and compared with those of the meso-dithiole BODIPY. [Display omitted]