RUI: SYNTHESIS, STRUCTURE, AND REACTIVITY OF ALKYNE-LINKED OLIGOPHENYLENES AND CYCLOPHENYLENES

California Polytechnic State University Foundation, San Luis Obispo CA

Investigators

Abstract

In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Professor Derik K. Frantz of the Department of Chemistry and Biochemistry at California Polytechnic State University, San Luis Obispo is developing three-dimensional, cyclic and multicyclic molecular structures. These unique molecules are of fundamental interest as the researchers explore their unusual properties and investigate their potential applications in functional materials. A versatile synthetic strategy permits the creative design and construction of a wide variety of these molecules, which contain nanometer-scale rings that are clamped or tethered by short, linear linkers (alkynes). Outside of the laboratory, the Broader Impacts of this work support Professor Frantz's efforts to improve student success and increase inclusivity in organic chemical education through the production and presentation of video lessons to help students understand challenging concepts and to supplement an active, engaging classroom experience. Professor Frantz and his undergraduate research group aim to synthesize and investigate a variety of alkyne-linked oligophenylenes and cyclophenylenes. The synthetic methodology incorporates alkyne linkers as templates for the generation of phenylene- and ethynylene-based macrocyclic and multicyclic systems. In the targeted structures, alkyne groups internally link macrocycles to form structures with constrained molecular geometries. The researchers are studying the effect that this constrain imparts on the molecules' static and dynamic structures and on their reactivities and properties. The constrained targets include highly strained systems, twisted and helical structures, and designs possessing interlinked units. To construct these molecules, the researchers will apply a synthetic strategy that features robust, transition metal-catalyzed, C-C bond-forming reactions. This transferrable and modifiable approach will generate a variety of creative and unprecedented structures. Undergraduate students contributing to this project are to have an immersive research experience and gain significant practical scientific training and familiarity with advanced organic chemical concepts. 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.