Novel three dimensional organic molecules have attracted great interest owing to their intriguing structures, potential host-guest interactions and multifunctional cavities for promising molecular recognition and assembly. Prominent examples such as corannulenes and calixarenes well developed to show versatile applications in chemistry and material sciences are in general built by rigid aromatic rings. The bulky EMind and Eind groups, initially designed as powerful protecting groups for elusive multiple bonded main-group-element species, show unique molecular stereo controlling capability, which could be utilized as specific building blocks (Figure 1) . On the other hand, imine, as a reversible dynamic unsaturated bond, has the characteristics of easy formation, catalysis and useful pivot in topological chemistry. In this context, two novel Janus tripod molecules with perpendicularly tri-linked EMind or Eind struts were successfully synthesized by condensation reaction between EMindNH<sub>2</sub> or EindNH<sub>2</sub> and 1,3,5-benzenetricarboxaldehyde (Figure 1) in excellent yields. The single crystal analysis intuitively shows unique cavity of these molecules which can be potentially used for the molecular recognition and host-guest complexation. In addition, the photophysical property was further investigated with computation studies. The cavity and thermal stability were studied by gas adsorption and thermogravimetric analysis respectively. It has been revealed that the key EMind or Eind groups are not only used as bracing blocks but also play a vital role to stabilize the imine pivots, well protecting the unsaturated C=N double bonds from oxidation and endowing the frameworks with highly rigidness and thermal stability.

Synthesis of novel Janus tripod molecules constructed by bulky stereo controlling eMind or eIND groups

ACS Spring 2022

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