Macrocycles in Biotechnology
Molecular Recognition → Functional Biomaterials
Nature relies on highly selective molecular recognition to regulate biological processes. Inspired by these systems, we design cavity-containing macrocycles that mimic biological recognition events and assemble them with polymers and biopolymers through multiple weak interactions. These supramolecular biomaterials exhibit tunable chemical and physical properties, including stimuli responsiveness, molecular recognition, sensing, and therapeutic functionality.
- Small (2026): e74588
- Biomacromolecules (2026) 27 (7): 4523–4541
- RSC Medicinal Chemistry, 2021, 12, 2022-2030
- ACS Nano, 2018, 12, 8029–8036
Targeting Gram-Negative Pathogens through Molecular Recognition
The rapid emergence of antibiotic-resistant bacterial pathogens poses a major global health challenge and underscores the urgent need for new therapeutic strategies. Our research harnesses the versatility of macrocyclic host–guest chemistry to develop innovative supramolecular therapeutics that target bacterial virulence rather than bacterial viability. By disrupting key virulence pathways in Gram-negative bacteria, we aim to reduce pathogenicity while minimizing the selective pressure that drives antibiotic resistance. Through the rational design of functional macrocycles, our work seeks to establish new molecular platforms for combating multidrug-resistant bacterial infections.
Molecular Recognition & Biosensing
We design and develop macrocyclic receptors that selectively recognize biologically important ions and small molecules. Our research focuses on cavity-containing organic molecules with complementary binding sites that enable selective and cooperative recognition of halides, pyrophosphate, amides, diamides, and other biologically relevant molecules. By harnessing these molecular recognition properties, we develop new strategies for sensing and controlling biologically relevant chemical species.
- Cryst. Growth & Des., 2020, 20, 4, 2367
- Chem. Sci. 2018, 9, 1358
- J. Org. Chem., 2017, 82, 5198
- Chem. Eur. J. 2015, 21, 9556
- Chem. Eur. J. 2014, 20, 15144
Macrocycles and Halogen Bond Materials
Halogen-Bonded Functional Materials
Halogen bonding has emerged as a powerful and highly directional noncovalent interaction for constructing functional materials. We investigate halogen-bonded supramolecular assemblies based on block copolymers, homopolymers, and cavity-containing macrocycles to understand how polymer architecture governs self-assembly, morphology, and material properties.
Halogen-Bonded Supramolecular Architectures
Our group explores halogen bonding as a versatile alternative to hydrogen bonding for constructing discrete supramolecular assemblies. Using resorcinarene-based macrocycles as multivalent halogen bond donors and acceptors, we develop cavitands, molecular capsules, dimeric assemblies, and supramolecular polymers with precisely controlled architectures and functions.
- The Chemical Record 2021, 20, 386
- Angew. Chem. Int. Ed. 2016, 55, 14033
- J. Am. Chem. Soc. 2015, 137, 10406
- Angew. Chem. Int. Ed. 2015, 54, 7303
Macrocycles in Crude Oil Research
Macrocycles as Asphaltene Dispersants
Asphaltene precipitation during crude oil production causes severe fouling, pipeline blockage, and increased operating costs. Our laboratory is developing amphiphilic macrocycles as a new generation of asphaltene dispersants that prevent aggregation through supramolecular interactions. These studies provide molecular insights while advancing more efficient and sustainable technologies for the petroleum industry.
Macrocycles in Molecular Recognition
Macrocycles as Ion-Pair Receptors
Selective recognition of ion pairs remains a fundamental challenge in supramolecular chemistry. By strategically functionalizing resorcinarene and pyrogallarene macrocycles, we tailor receptor properties for cooperative binding of both cations and anions. We investigate these host–guest interactions using solution-phase NMR spectroscopy and gas-phase mass spectrometry to understand the fundamental principles governing ion-pair recognition.
Hydrogen/Deuterium Exchange in Supramolecular Systems
Hydrogen/deuterium exchange (HDX) provides unique insights into the structure, dynamics, and stability of supramolecular assemblies in the gas phase. Our studies of resorcinarene and pyrogallarene host–guest complexes reveal proton-transfer pathways and hydrogen-bonding networks, offering mechanistic understanding of supramolecular organization and contributing to the structural characterization of complex molecular assemblies.
Templating Molecular Capsules
Resorcinarenes are versatile building blocks for constructing self-assembled molecular capsules through template-directed assembly. We investigate how guest molecules control the formation of inclusion complexes, dimeric and hexameric capsules, tubular assemblies, and covalently linked cages. These confined supramolecular environments provide opportunities for selective molecular encapsulation, stabilization of reactive species, and host–guest chemistry.
The Beyeh Laboratory 