Exploiting the Redox Chemistry of the Triphenylmethyl (Trityl) Group: Development of Small Molecule Delivery Agents, Magnetic Materials, and Metal Nanoclusters

University Of California-Santa Barbara, Santa Barbara CA

Investigators

Abstract

With the support of the Chemical Synthesis program in the Division of Chemistry, Professor Trevor Hayton of the University of California Santa Barbara will study the development of the triphenylmethyl (trityl) group as a carrier for a diverse array of molecular cargo. The cargo molecules include enzyme intermediates, mammalian signaling molecules, and metal atoms. The trityl forms weak carbon-element bonds due to the high stability of its free radical form, thus it is expected to release these cargo molecules under mild conditions. These cargo molecules will be used to study chemical processes relevant to the global nitrogen cycle, mammalian bioregulation, and the synthesis of magnetic nanomaterials. This research will provide excellent training to undergraduate and graduate students in the synthesis and characterization of air-sensitive inorganic and organometallic clusters and complexes, preparing them for careers in academia and industry. In addition, Professor Hayton will develop a new undergraduate organic chemistry laboratory describing the synthesis and characterization of the trityl radical. This laboratory will introduce undergraduate students to free radical chemistry, which is infrequently covered in the undergraduate chemistry curriculum, but is finding an increased prominence within the modern chemical sciences. This project will explore the synthesis and development of triphenylmethyl-containing small molecule delivery agents for a variety of applications. The triphenylmethyl (trityl) group is stable in its neutral (radical) form, which enables facile small molecule release upon application of external stimuli, such as oxidation and photolysis. Specific targets include delivery agents for carbon disulfide and sulfur monoxide. The former is a poorly-understood mammalian gasotransmitter, whereas the latter is a proposed intermediate in the nitrous oxide reductase catalytic cycle. Professor Hayton will also develop trityl-containing carrier molecules for vanadium, chromium, and cobalt, which will be used to generate new magnetic materials and metal nanoclusters. These materials are of interest for a variety of applications, such as memory storage and quantum computing. The Hayton group will achieve their research goals via new synthetic methodology development, spectroscopic characterization, and magnetism measurements. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.