Structural diversity in 1D hydrogen-bonded chains assembled through bis(triazole) self-association

Abstract

We show that simple phenyl-1,3-bis(triazole) groups dimerise in solution. Dimerisation of these compounds in CDCl₃ is too strong to measure by ¹H NMR spectroscopy, and dimerisation in 9 : 1 CDCl₃ : d₆-acetone is relatively strong (K_dimerisation = 1360 or 4460 M⁻¹, depending on whether preorganising methyl groups are absent or present, respectively). A ditopic compound 1 containing two bis(triazole) groups crystallises to give hydrogen-bonded chains. Four different crystal structures were obtained, all of which are 1D chains, and all of which contain small solvent-filled channels. While the overall structure and packing are similar, diversity in the hydrogen bonding arrangements is observed due to the possibility of the triazole groups adopting either syn or anti conformations.