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

doi:10.1002/anie.201806787

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

39 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 pK_a to give the excited state pK_a ^*>20 in ethanol.

Original language	English
Pages (from-to)	14742-14746
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	45
DOIs	https://doi.org/10.1002/anie.201806787
State	Published - 5 Nov 2018

Keywords

excited state
fluorene
photobase
proton transfer
transient spectroscopy

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201806787

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title = "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.",

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AU - Sheng, Wei

AU - Nairat, Muath

AU - Pawlaczyk, Patrick D.

AU - Mroczka, Elizabeth

AU - Farris, Benjamin

AU - Pines, Ehud

AU - Geiger, James H.

AU - Borhan, Babak

AU - Dantus, Marcos

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AB - 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.

KW - excited state

KW - fluorene

KW - photobase

KW - proton transfer

KW - transient spectroscopy

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Ultrafast Dynamics of a “Super” Photobase

Abstract

Keywords

ASJC Scopus subject areas

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