UC Irvine

Controlling molecular reactivity, assembly, and selectivity remains a challenge. This dissertation develops strategies for directing chemical and biochemical transformations across nanomaterials, small molecules, and proteins.The Vortex Fluidic Device (VFD) is a versatile thin-film microfluidic platform that has been applied across more than 100 reports in biochemistry, chemistry, materials science, food processing, and medicine. By imparting mechanical energy into solution, the VFD can direct chemical and biochemical transformations, and when combined with the magnetic fields surrounding the device tube, offers enhanced control over molecular reactivity and assembly. The first part of this dissertation explores how the VFD's topological fluid flows impose chirality and structural order on single-walled carbon nanotube (SWCNT) assemblies, demonstrating that simply reversing the tube's rotational direction preferentially produces R- or S-chiral lemniscate structures. Building on these findings, we investigate whether chiral induction can be further amplified through contact electrification effects and applied fields, including the influence of Earth's magnetic field on chiral control at the submicron scale. These insights inform the development of VFD-controlled peptide macrocyclization, where directional fluid flow is harnessed to accelerate intramolecular cyclization in aqueous conditions, improving green chemistry metrics and enabling selective homochirality without the use of a chiral auxiliary. The second half of the thesis shifts focus to synthetic chemistry and bioconjugation. A catalyst-free, three-component reaction that couples azidomaleimides, aldehydes, and secondary amines to form amidinomaleimides under mild conditions. As reported in The Journal of Organic Chemistry, this method creates complex, multifunctional molecules in a one-pot reaction through electrophilic azide activation and enamine–azide cycloaddition. This work expands the synthetic utility of maleimides and provides new routes to multifunctional small molecules. Building on these findings, a novel protein bioconjugation platform is introduced that enables selective modification with the electron deficient azidomaleimide at the His6 epitope with nearly quantitative yields. This discovery opens new avenues for bioconjugation research and applications. Together, these studies demonstrate how physical flow fields, electronic activation, and molecular design can be leveraged to control chemical reactivity across diverse systems, offering new tools for nanomaterials processing, synthetic chemistry, and protein engineering.