Synthesis and crystal structure of 1,1'-bis-{4-(pyridin-2-yl)-1,2,3-triazol-1-ylmeth-yl}ferrocene, and its complexation with CuI

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 76; no. Pt 10; pp. 1582 - 1586
• Main Authors: Pokharel, Uttam R, Naquin, Aaron P, Brochon, Connor P, Fronczek, Frank R
• Format: Journal Article
• Language: English
• Published: International Union of Crystallography 01-10-2020
• Subjects: 1,1′-bis(pyridyltriazoylmethyl)ferrocene; click reaction; copper(i) complex; crystal structure; disubstituted ferrocene; Research Communications; tetradentate ligand
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989020011901

The title compound, [Fe(C13H11N4)2], was synthesized starting from 1,1'-ferro-cene-di-carb-oxy-lic acid in a three-step reaction sequence. The di-carb-oxy-lic acid was reduced to 1,1'-ferrocenedi-methanol using LiAlH4 and subsequently converted to 1,1'-bis-(azido-meth-yl)ferrocene in the presence of NaN3. The diazide was treated with 2-ethynyl-pyridine under 'click' conditions to give the title compound in 75% yield. The FeII center lies on an inversion center in the crystal. The two pyridyl-triazole wings are oriented in an anti conformation and positioned exo from the FeII center. In the solid state, the mol-ecules inter-act by C-H⋯N, C-H⋯π, and π-π inter-actions. The complexation of the ligand with [Cu(CH3CN)4](PF6) gives a tetra-nuclear dimeric complex.The title compound, [Fe(C13H11N4)2], was synthesized starting from 1,1'-ferro-cene-di-carb-oxy-lic acid in a three-step reaction sequence. The di-carb-oxy-lic acid was reduced to 1,1'-ferrocenedi-methanol using LiAlH4 and subsequently converted to 1,1'-bis-(azido-meth-yl)ferrocene in the presence of NaN3. The diazide was treated with 2-ethynyl-pyridine under 'click' conditions to give the title compound in 75% yield. The FeII center lies on an inversion center in the crystal. The two pyridyl-triazole wings are oriented in an anti conformation and positioned exo from the FeII center. In the solid state, the mol-ecules inter-act by C-H⋯N, C-H⋯π, and π-π inter-actions. The complexation of the ligand with [Cu(CH3CN)4](PF6) gives a tetra-nuclear dimeric complex.