H-Bond Mediated Self-Assembly 1-Dimensional Array of 3,6-Bis(3′-Pyridyl)-1,2,4,5-Tetrazine with Trimesic Acid

ABSTRACT

3,6-Bis(3′-pyridyl)-1,2,4,5-tetrazine was prepared by reaction of 3-cyanopyridine with hydrazine. Slow evaporation of 3,6-bis(3′-pyridyl)-1,2,4,5-tetrazine with trimesic acid, in a 2:1 molar ratio in methanol afforded single crystals of 1 C₃₃H₂₂N₁₂O₆, suitable for X-ray analysis. The product was characterized by spectroscopic and single-crystal X-ray diffraction studies. The hydrogen bond mediated self-assembly of 3,6-bis(3′-pyridyl)-1,2,4,5-tetrazine with trimesic acid molecules generates 1-dimensional multi-compartmental arrays in the solid state as revealed by X-ray crystallographic analysis. The crystal structure of 1 is monoclinic with a = 28.445(3), b = 6.7088(10), c = 33.846(4) A˚ , α = 90°, β = 108.112(7°, γ = 90°, Z = 8, and space group C2/c. The directional intermolecular hydrogen bonding between 3,6-bis(3′-pyridyl)-1,2,4,5-tetrazine and trimesic acid molecules uses O − H … N and C − H … O interactions, together with intramolecular C − H … N hydrogen bonding, to build up the one-dimensional network structure.

Keywords:

• hydrogen-bond
• monoclinic
• multi-compartmental arrays
• one-dimensional network
• self-assembly
• solid state
• trimesic acid

Acknowledgments

This work was supported by the National Science Council, Taiwan (ROC), and Tamkang University.

Notes

Symmetry codes: (i) 1/2 − x, 1/2 − y, − z; (ii) x, 1 + y, z; (iii) 1 − x, y, 1/2 − z; (iv) 1/2 − x, 1/2 − y, − z; (v) 1 − x, − 1 + y, 1/2 − z.