Self-Assembly with 2,6-Bis(1-(pyridin-4-ylmethyl)-1H-1,2,3-triazol-4-yl)pyridine: Silver(I) and Iron(II) Complexes

Abstract

A new “click” ligand, 2,6-bis(1-(pyridin-4-ylmethyl)-1H-1,2,3-triazol-4-yl)pyridine (L) featuring a tridentate 2,6-bis(1,2,3-triazol-4-yl)pyridine (tripy) pocket and two pyridyl (py) units was synthesized in modest yield (42%) using the copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The coordination chemistry of the ligand with silver(I) and iron(II) ions was examined using a battery of solution (1H and DOSY (diffusion ordered spectroscopy) nuclear magnetic resonance (NMR), infrared and absorption spectroscopies, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS)), and solid state (X-ray crystallography, elemental analysis) techniques. When treated with silver(I) ions, the ligand forms discrete [Ag(L)]+ (X−, where X− = BF4−, NO3− or SbF6−) complexes in dimethyl sulfoxide (DMSO) solution but these complexes crystallize as coordination polymers. The addition of [Fe(H2O)6](BF4)2 to an acetonitrile solution of the ligand forms the expected monomeric octahedral [Fe(L)2]2+ complex and treatment of the iron(II) complex with AgBF4 generates a heterometallic linear coordination polymer.

Recognition Properties and Self‐assembly of Planar [M(2‐pyridyl‐1,2,3‐triazole)2]2+ Metallo‐ligands

“…We investigated the self‐assembly properties of the metallo‐ligands and host‐guest systems with silver(I) ions. It was hoped that the use of labile, coordinatively pliant Ag I ions would allow the formation of larger assemblies or networks while still leaving the host‐guest interaction as the dominant factor in the self‐assembly process …”

“…It was hoped that the use of labile, coordinatively pliant Ag I ions would allow the formation of larger assemblies or networks whiles till leaving the host-guest interaction ast he dominantf actor in the self-assembly process. [29] Results and Discussion…”

Supramolecular chemistry of two new bis(1,2,3-triazolyl)pyridine macrocycles: metal complexation, self-assembly and anion binding

“…1): the 3,5-btp motif has been extensively studied in the context of anion recognition, and deriva- tives containing an N-alkylated pyridinium group and/or halotriazole groups for halogen bonding have proven to be highly effective in this regard. [21][22][23] The 2,6-btp motif has primarily been used for coordination to a wide range of metal ions, [24][25][26][27][28][29][30][31][32][33] but has also been used for anion recognition [34][35][36] and anion binding catalysis 37 (the reader is directed to a recent review for a comprehensive overview of the chemistry of the 2,6-btp motif 20 ). Interestingly, Byrne and Gunnlaugsson have also demonstrated that the 2,6-btp motif can self-recognise through C-H⋯N hydrogen bonding, and have used this recognition to template the formation of catenanes.…”

Supramolecular chemistry of two new bis(1,2,3-triazolyl)pyridine macrocycles: metal complexation, self–assembly and anion binding

“…19,20 Two isomers of the btp motif have been commonly studied (Figure 1): the 3,5-btp motif has been extensively studied in the context of anion recognition, and derivatives containing an N-alkylated pyridinium group and/or halotriazole groups for halogen bonding have proven to be highly effective in this regard. [21][22][23] The 2,6-btp motif has primarily been used for coordination to a wide range of metal ions, [24][25][26][27][28][29][30][31][32][33] but has also been used for anion recognition [34][35][36] and anion binding catalysis 37 (the reader is directed to a recent review for a comprehensive overview of the chemistry of the 2,6-btp motif 20 ). Interestingly, Byrne and Gunnlaugsson have also demonstrated that the 2,6-btp motif can selfrecognise through C-H•••N hydrogen bonding, and have used this recognition to template the formation of catenanes.…”