Photochemistry of "super" photoacids. 3: Excited-state proton transfer from perfluroalkylsulfonyl-substitutued 2-naphthols

Caroline Clower, Kyril M. Solntsev*, Janusz Kowalik, Laren M. Tolbert, Dan Huppert

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


As a continuation of our efforts in the synthesis and investigation of novel "super" photoacids, in this article we report on the effect of fluoroalkanesulfonyl groups on the photoacidity of 2-naphthol. These groups, known to be the strongest electron-withdrawing substituents, were expected to increase the photoacidity to a greater extent as compared to previously described cyano- and methanesulfonyl groups. Indeed, we have found that 6-perfluoromethylsulfonyl-2-naphthol (6F3) is more acidic in the ground state and noticeably more acidic in the excited state than is previously synthesized 6-cyano-2-naphthol. The unusually short fluorescence lifetimes of the naphthol and the conjugated anion, which are explained by effective resonance/intramolecular charge transfer, mask the extended photoacidity of 6F3. Photochemical investigations of 6-perfluorohexylsulfonyl-2-naphthol (6F13) in protic solvents are complicated by aggregation.

Original languageEnglish
Pages (from-to)3114-3122
Number of pages9
JournalJournal of Physical Chemistry A
Issue number13
StatePublished - 4 Apr 2002


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