CAS: Superelectrophiles in the Synthesis of Materials for Organic-based Electronics

Northern Illinois University, Dekalb IL

Investigators

Abstract

With this award, the Chemical Synthesis Program of the Division of Chemistry is supporting the research of Professor Douglas Klumpp of the Department of Chemistry and Biochemistry at Northern Illinois University. Professor Klumpp and his team of students are developing new ways to make twisted and three-dimensionally constrained molecules with extended systems of electrons to be used in organic-based electronic devices such as organic light-emitting diodes (OLEDs). Compounds called super-electrophiles that trigger difficult carbon-carbon bond construction are being generated and used to access these complex targets. This program promises to explore alternative ways to make new compounds for study as components of organic-based semi-conductors, solid-state solar cells, and photo-responsive materials. This project will also serve to train a diverse group of graduate, undergraduate, and high school students in synthetic organic chemistry particularly toward materials-related target structures. Professor Klumpp is also leading outreach activities to third-graders and creating science-related artwork to broaden the impact of the program to a larger audience. New synthetic routes to aryl-substituted fluorenes and related spirocyclic compounds are valuable as they open up new avenues into organic-based electronic devices. The Klumpp research group has previously demonstrated that super-electrophilic chemistry can be used to efficiently prepared functionalized heterocycles and hydrocarbon-based arenes. With the current award, Professor Klumpp and his students are using superelectrophilic reactions to develop new synthetic approaches to aryl-substituted fluorenes and related spirocycles, to modify known OLED-type materials with Diels-Alder, Friedel-Crafts, and cyclization reactions, and to synthesize elongated, orthogonal, conjugated arene systems. These transformations provide potential advantages over alternative synthetic routes by reducing dependence on transition metal catalysts and organic solvents. Most importantly, the routes proposed provide for convergent entry into value-added cyclic systems with potentially useful physical organic properties. Overall, the research conducted under this award provides orthogonal approaches to important materials-related targets and will help to elucidate how the fundamental reactivity of super-electrophiles can be exploited in an array of C-C bond-forming reactions. 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.