Title

Chemical strategies towards the synthesis of 2-substituted calix[4]resorcinarenes for upper-rim functionalization

Standing

Undergraduate

Type of Proposal

Oral Research Presentation

Challenges Theme

Open Challenge

Your Location

Windsor, Ontario

Faculty

Faculty of Science

Faculty Sponsor

John F. Trant

Abstract/Description of Original Work

Supramolecular chemistry is the interdisciplinary study of the chemical, physical and biological properties of complex chemical species beyond individual molecules themselves. As of late, this field of study has become increasingly important due to the multifaceted applications of supramolecular complexes (hosts) for interacting with and transporting a variety of guest molecules within biological systems. A prime example of such host complexes are Calix[4]resorcinarenes; bowl-shaped macrocyclic compounds consisting of 4 phenolic units (a benzene ring with hydroxyl groups) linked together by methylene (single carbon containing) bridges. These macrocycles are involved in molecular recognition and are known to facilitate the solubility of hydrophobic compounds due to the presence of multiple hydroxyl groups. The controlled design and synthesis of these resorcinarenes can be used to invoke specific host-guest interactions depending on the substituent (chemical group) attached to the resorcinarene. However, this field remains limited to simpler compounds without reliable methods of synthesis that yield macrocycles with more diverse substitution patterns. For this reason, little is known about the specific effects of different substituents on the functionality of resorcinarenes. This project aims to develop and optimize unified chemical strategies to synthesize a variety of Calix[4]resorcinarenes with different substituents and study their functionalizing effects within host-guest chemistry (i.e. the types of guest molecules that can bind and the solubility of these host-guest complexes). Ultimately, this approach broadens the scope of potential applications of these macrocycles by introducing novel functionality.

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Chemical strategies towards the synthesis of 2-substituted calix[4]resorcinarenes for upper-rim functionalization

Supramolecular chemistry is the interdisciplinary study of the chemical, physical and biological properties of complex chemical species beyond individual molecules themselves. As of late, this field of study has become increasingly important due to the multifaceted applications of supramolecular complexes (hosts) for interacting with and transporting a variety of guest molecules within biological systems. A prime example of such host complexes are Calix[4]resorcinarenes; bowl-shaped macrocyclic compounds consisting of 4 phenolic units (a benzene ring with hydroxyl groups) linked together by methylene (single carbon containing) bridges. These macrocycles are involved in molecular recognition and are known to facilitate the solubility of hydrophobic compounds due to the presence of multiple hydroxyl groups. The controlled design and synthesis of these resorcinarenes can be used to invoke specific host-guest interactions depending on the substituent (chemical group) attached to the resorcinarene. However, this field remains limited to simpler compounds without reliable methods of synthesis that yield macrocycles with more diverse substitution patterns. For this reason, little is known about the specific effects of different substituents on the functionality of resorcinarenes. This project aims to develop and optimize unified chemical strategies to synthesize a variety of Calix[4]resorcinarenes with different substituents and study their functionalizing effects within host-guest chemistry (i.e. the types of guest molecules that can bind and the solubility of these host-guest complexes). Ultimately, this approach broadens the scope of potential applications of these macrocycles by introducing novel functionality.