Diol-Mediated Benzannulation for Polyaromatic Hydrocarbon (PAH) Construction

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In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Professor Michael J. Krische of the Department of Chemistry at the University of Texas at Austin is applying catalytic reactions developed in his laboratory to the construction of polycyclic aromatic hydrocarbons. Polycyclic aromatic hydrocarbons are used in commercial electronic display screens and show promise in a range of other applications, for example, high-speed electronics and solar cells. The project involves expertise spanning the fields of organic chemistry, homogenous transition metal catalysis, and materials chemistry. Professor Krische mentors and trains undergraduates, graduate students and postdoctoral research associates, including students from groups historically underrepresented in the sciences. Professor Krische founded and continues to co-organize a state-wide organic chemistry symposium in Texas, known as ?TEXSYN.? This annual event, which attracts 100 attendees, includes a poster session and short talks by undergraduate and graduate students, connecting students with leading researchers to design new routes to commodity and fine chemicals. Professor Michael J. Krische's laboratory has pioneered a new class of catalytic carbon carbon bond formations that directly convert lower alcohols to higher alcohols. These processes bypass the use of stoichiometric metals and discrete alcohol-to-carbonyl redox reactions, which are hazardous and contribute to waste generation. Based on this new reactivity pattern, diol-mediated benzannulation reactions were developed. Under the aegis of NSF support, this benzannulation methodology will be used to advance new strategies for the synthesis of polycyclic aromatic hydrocarbons and related nanographene materials, which are of significant importance in the growing field of molecular electronics. Whereas the field of polycyclic aromatic hydrocarbon synthesis is largely reliant on cross-coupling technology, this diol-mediated benzannulations could unlock broad and new polycyclic aromatic hydrocarbon chemical space.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.