Highly chromic, proton-responsive phenyl pyrimidones.

Jyothi Dhuguru, Chirag Gheewala, N S Saleesh Kumar, James N Wilson

Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33124, USA.

Organic letters 2011 Aug 19

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Aryl pyrimidones are pharmacologically relevant compounds whose optical properties have only been partially explored. We report the synthesis and optical characterization of a series of aryl- and diaryl-2(1H)-pyrimidones. The electronic transitions of these chromophores are modulated by the extent of conjugation between the pendant phenyl ring and the pyrimidone core as well as the presence of electron-donating auxochromes. Monoprotonation of the pyrimidone ring results in large hyperchromic and bathochromic shifts as well as switching of fluorescence making these phenyl pyrimidones of interest as sensory materials. © 2011 American Chemical Society

Citation

Jyothi Dhuguru, Chirag Gheewala, N S Saleesh Kumar, James N Wilson. Highly chromic, proton-responsive phenyl pyrimidones. Organic letters. 2011 Aug 19;13(16):4188-91