6-Hydroxyquinoline-N-oxides: A new class of "Super" photoacids

Kyril M. Solntsev*, Caroline E. Glower, Laren M. Tolbert, Dan Huppert

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


N-Oxidation of hydroxyquinolines leads to a dramatic increase in their excited-state acidity. Time-resolved and steady-state emission characterization of 6-hydroxyquinoline-N-oxide and 2-methyl-6-hydroxyquinoline-N-oxide reveals a rich but less complex proton-transfer behavior than that of its parent hydroxyquinoline. The electronic effect of the oxidized heterocyclic nitrogen atom makes the excited state both less basic and more acidic than the parent and adds hydroxyquinoline N-oxides to the class of high-acidity excited-state proton donors in photochemistry and photobiology. Adiabatic photoinduced proton transfer is accompanied by the efficient nonreversible deoxygenation and 1-2 oxygen migration.

Original languageEnglish
Pages (from-to)8534-8544
Number of pages11
JournalJournal of the American Chemical Society
Issue number23
StatePublished - 15 Jun 2005


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