Ultrafast Dynamics of a “Super” Photobase

Wei Sheng, Muath Nairat, Patrick D. Pawlaczyk, Elizabeth Mroczka, Benjamin Farris, Ehud Pines, James H. Geiger, Babak Borhan, Marcos Dantus

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Molecular reactivity can change dramatically with the absorption of a photon due to the difference of the electronic configurations between the excited and ground states. Here we report on the discovery of a modular system (Schiff base formed from an aldehyde and an amine) that upon photoexcitation yields a more basic imine capable of intermolecular proton transfer from protic solvents. Ultrafast dynamics of the excited state conjugated Schiff base reveals the pathway for proton transfer, culminating in a 14-unit increase in pKa to give the excited state pKa *>20 in ethanol.

Original languageEnglish
Pages (from-to)14742-14746
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number45
DOIs
StatePublished - 5 Nov 2018

Keywords

  • excited state
  • fluorene
  • photobase
  • proton transfer
  • transient spectroscopy

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