Synthesis of Dynamic N-acylhydrazone-Based Macrocycles

Abstract

We present herein synthesis of novel [2+2] and [3+3] N-acylhydrazone-based macrocycles using a pool of dialdehydes and dihydrazides, under thermodynamic control. The resulted macrocycles, which were assigned triangular and rectangular shapes, were characterised in the solid state. The rectangular macrocycle was further investigated in solution by absorption and emission spectroscopy. Additionally, the rectangular macrocycle was used in various assays to investigate the hosting capacity towards various guests using NMR, HRMS, UV-Vis and fluorescence spectroscopy, taking advantage of the emissive behaviour of the resulted compound. Theoretical calculations regarding structure and properties of the novel compounds were in agreement with the experimental details. The experimental data showed intriguing results toward tetra-n-butylammonium fluoride.