UROP Proceedings 2020-21

School of Science Department of Chemistry 10 Development of New Catalytic Organic Processes Supervisor: SUN Jianwei / CHEM Student: YAN Qiaolin / CHEM Course: UROP1000, Summer Enantioenriched triarylmethanes with heterocyclic structures are critical components in drugs. Described here is a new approach to access this important and challenging target in organic synthesis via chiral phosphoric acid-catalyzed reductive dehydroxylation of tertiary alcohols. This study presents the first reported success of a directing-group-free design in the asymmetric catalysis of triarylmethanes. The suitable chiral phosphoric acid catalyzed the mild reductive dehydroxylation to form diverse heterocycle-containing triarylmethanes with excellent efficiency and enantioselectivity. Control experiments, kinetic study, and non-linear effects revealed the kinetic resolution in the rate-determining carbocation formation step to determine the enantioselectivity. Design and Synthesis of Functional AIE luminogens and Exploration of their Biological Applications Supervisor: TANG Benzhong / CHEM Student: WANG Lily Ueh-hsi / CHEM Course: UROP1100, Fall With the discovery of aggregation-induced emission, materials leveraging some distinct features in the aggregate state have been flourishing in the past twenty years. Cocrystal, with two or more compounds aggregate by noncovalent interactions, is an arising field of great versatility in terms of tunable physicochemical properties. To develop materials with photothermal properties, self-assemble cocrystal made from simple preparation is one promising direction. In 2018, the first cocrystal with the ability of nearinfrared and heat conversion came to place. Here, inspired by the recent breakthrough in aggregate science, a cocrystal is reported, which successfully demonstrated photothermal properties in the preliminary investigation. Design and Synthesis of Functional AIE luminogens and Exploration of their Biological Applications Supervisor: TANG Benzhong / CHEM Student: LI Sijie / CHEM Course: UROP1000, Summer Aggregation-induced emission (AIE) luminogens (AIEgens) are a type of molecule showing emission under aggregate state. The powerful emission in aqueous media, a common poor solvent for organic compounds, demonstrates a wide application of this novel type of molecule. AIE-active moiety TBP has been reported for the ability to generate reactive oxygen species (ROS) for antibacterial and antitumor effect. Whereas quinone methide (QM) has been found to be effective in inhibiting antioxidant system for resisting ROSinduced apoptosis in cancer cells. Therefore, in this study, a synergistic hybrid AIEgen TBP-QM is designed and synthesized for cancer treatment. TBP-QM is expected to act as a novel theranostic agent with the ability to disturbing cancer cell antioxidant system, inducing cell death by ROS invasion in a site-specific way, and at the same time allowing on-site bioimaging.

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