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Ultrafast Dynamics of a "Super" Photobase.


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.

SUBMITTER: Sheng W 

PROVIDER: S-EPMC7358037 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Ultrafast Dynamics of a "Super" Photobase.

Sheng Wei W   Nairat Muath M   Pawlaczyk Patrick D PD   Mroczka Elizabeth E   Farris Benjamin B   Pines Ehud E   Geiger James H JH   Borhan Babak B   Dantus Marcos M  

Angewandte Chemie (International ed. in English) 20181012 45


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, culmin  ...[more]

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