Organic Synthesis · Supramolecular Chemistry

Molecular Self-Assembly via Alkene Metathesis

Synthesized porous organic macrocycles by using molecular geometry to guide pentagonal assembly through dynamic covalent (DCvC) alkene metathesis chemistry.

Macrocycle design concept based on tetrahedral carbon geometry — Schematic representation of the macrocycle design concept based on tetrahedral carbon geometry.

Overview

This project explored the synthesis of organized porous macrocycles using molecular geometry as a design rule. The core concept was to exploit the approximately 109° bond angle of sp³ carbons to direct the formation of pentagonal structures, whose interior angle is close to 108°. The broader motivation was to create symmetric molecular cavities that could support host–guest interactions and future applications in areas such as molecular recognition, gas adsorption, and organic electronics.

My role

I worked in Prof. Dennis D. Cao’s organic materials lab at Macalester College, contributing to monomer synthesis, alkene metathesis reaction optimization, product characterization, and interpretation of macrocycle formation.

Key outcomes

Synthesized macrocyclic structures through dynamic covalent (DCvC) alkene metathesis chemistry.
Applied molecular geometry to guide the assembly of pentagonal organic macrocycles.
Obtained APCI-MS evidence supporting formation of a macrocycle with an approximately 14 Å cavity.
Presented the work through undergraduate research venues and an ACS National Meeting poster session.