Synthesis and Structure of D3h-Symmetric Triptycene Trimaleimide

Cristiano Zonta,Anthony Linden,Martin Lutz,Ottorino De Lucchi

doi:10.3390/molecules15010226

Abstract

A new D3h symmetric triptycene derivative has been synthesized with the aim of obtaining molecules that are able to assemble into porous structures, and can be used in the development of new ligands. The synthesis involves a Diels-Alder reaction as the key step, followed by an oxidation and the formation of a maleimide ring. Triptycene trimaleimide furnished single crystals which have been analyzed by means of X-ray diffraction.

Highlights

The advantages offered by high-symmetry molecules are widely recognized in catalysis and can be readily applied in several other fields
By using the strategy of molecular tectonics, a hypothetical molecule possessing D3h symmetry and linking sites at the extremities might lead to a porous structure via the formation of a hexagonal network (Figure 1). [12] A tecton based on a triptycene quinoxaline ligand has been used for the formation of pores
We chose to synthesize a related triptycene-based tecton with D3h symmetry in the hope that it would assemble in the solid state into a honeycomb structure with large pores

Summary

Introduction

The advantages offered by high-symmetry molecules are widely recognized in catalysis and can be readily applied in several other fields (e.g., material science, liquid crystal technology and nanoscience). By using the strategy of molecular tectonics, a hypothetical molecule possessing D3h symmetry and linking sites at the extremities might lead to a porous structure via the formation of a hexagonal network (Figure 1). We chose to synthesize a related triptycene-based tecton with D3h symmetry in the hope that it would assemble in the solid state into a honeycomb structure with large pores. Hydrogen bonds, between suitably positioned donor and acceptor groups to directionally control the aggregation of the molecules.

Results

Conclusion