03/27/2024
By Kwok Fan Chow

The Kennedy College of Science, Department of Chemistry, invites you to attend a Ph.D. Research Proposal defense by Mubarak Ayinla entitled “Exploring Complex Dynamic Materials Based on the Nitroaldol Reaction.”

Degree: Doctoral
Date: Saturday, April 6, 2024
Time: 10 a.m.
Location: Olney, Room 518

Committee

  • Chair Prof. Olof Ramström, Department of Chemistry, University of Massachusetts Lowell
  • Prof. Mingdi Yan, Department of Chemistry, University of Massachusetts Lowell
  • Prof. Marina Ruths, Department of Chemistry, University of Massachusetts Lowell
  • Prof. Lawrence Wolf, Department of Chemistry, University of Massachusetts Lowell

Abstract:
Dynamic covalent chemistry (DCvC) is a pioneering subdiscipline that employs reversible covalent bond formation under thermodynamic control, enabling the synthesis of a vast array of materials with intricate architectures that have many applications across diverse fields, including biotechnology, drug discovery, molecular storage, and separation technologies.
Despite the advancement in the field, existing dynamic covalent reactions (such as boronate formation, Diels-Alder reaction, imine formation, disulfide formation, etc.) face challenges including lack of directionality, instability under certain conditions, and very limited potential for post-synthetic modifications. The nitroaldol reaction's unique attributes include its inherent directionality, ability to function under aqueous and ambient conditions, and stability. Notably, its β-hydroxy-nitro products harbor two highly versatile groups, facilitating their remarkable transformation into a diverse array of functional groups with widespread applications across various scientific fields.

Capitalizing on these unique features of the nitroaldol reaction, our strategy is centered on the synthesis of (un)precedented topologically complex materials, while significantly addressing key limitations in the field of DCvC. Through a systematic study of reaction conditions, catalytic environments, and feed concentrations, we strive to identify optimal conditions that favor the creation of desired topologies, thereby achieving structural precision and improved functionality.

The feasibility of our approach is demonstrated by the initial successful synthesis and characterization of structurally rigid aldehyde and nitroalkane monomers, as well as our observed successes thus far in developing some materials with intricate architectures. Characterization techniques, including NMR spectroscopy, high-resolution mass spectrometry, X-ray diffraction, and advanced analytical methods to evaluate the materials' emergent properties, further validate the potential of our methodology.

This study endeavors to develop an extensive library of dynamic materials susceptible to post-synthetic modifications, with properties tailored for environmental remediation, gas storage, and catalysis. Ultimately, our work aims to extend the underexplored nitroaldol chemistry to the dynamic materials’ domain, as we also plan to make theoretical contributions to the field of DCvC by developing atomically precise synthetic pathways of complex dynamic materials possessing the β-nitroalcohol, nitro-olefin, and olefin-linked motifs.

All interested students and faculty members are invited to attend.