The title compound, which has the highest symmetry among tetrapyridylmethane isomers, has been synthesized from tris(4-pyridyl)methane and 4-chloropyridine. The silver(I) complex of the title compound forms a three-dimensional, non-interpenetrated diamondoid network in a crystal.
The title compound, a prototypical chiral molecule based on a tetraarylmethane framework, has been synthesized in five steps from (2-pyridyl)-(3-pyridyl)ketone. X-ray crystallographic analysis revealed the tetraarylmethane framework of the molecule but did not determine the positions of the nitrogen atoms because the crystal is a racemic compound and the aryl groups are disordered in the crystal. The optical resolution of the title compound was achieved by chiral HPLC with a Chiralcel OD column. The CD spectra of the two fractions in acetonitrile exhibited opposite signs as expected for a pair of enantiomers. Their CD spectra are changed in 2 M HCl due to protonation. The calculated CD curve for the target molecule based on time-dependent density functional theory (TDDFT) reproduces the experimental result very well, thus suggesting that the first eluted fraction is the R isomer in terms of absolute configuration.
Tetrakis(2-pyridyl)methane forms a novel one dimensional coordination polymer complex with Ag(I) ion and two kinds of complexes different in coordination modes with Cu(II) ion, indicating its versatile ability as a symmetric tetradentate ligand.
A second polymorph of the title compound, C21H16N4, is reported. The original polymorph was solved by our group [Matsumoto et al. (2003 ▶). Tetrahedron Lett.
44, 2861–2864] in the monoclinic space group C2/c and refined to R = 0.050. Now the crystal structure of a tetragonal polymorph (space group P-421
c) has been solved and refined to R = 0.036. In the crystal, there are no strong intermolecular interactions. Reflecting the high symmetry of the molecular structure, the asymmetric unit is a quarter of the molecule, and the molecule exhibits S4 symmetry along the c axis in the crystal.
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