A new visible light triggered Arrhenius photobase and its photo-induced reactions

Joonyoung F. Joung; Jeeun Lee; Joungin Hwang; Kihang Choi; Sungnam Park

doi:10.1039/c9nj05404a

A new visible light triggered Arrhenius photobase and its photo-induced reactions

Joonyoung F. Joung, Jeeun Lee, Joungin Hwang, Kihang Choi, Sungnam Park

Department of Chemistry

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

Abstract

Arrhenius photobases are of potential use for excited state hydroxide ion dissociation (ESHID), photo-induced pOH jump experiments, and base-catalyzed reactions. However, previously studied Arrhenius photobases have to be excited by UV light and undergo ESHID reactions only in protic solvents. These characteristics have become a disadvantage to their application in many fields of research. In this work, we have designed and synthesized a new Arrhenius photobase (NO₂-Acr-OH), the ESHID reaction of which is readily triggered by visible light excitation. In contrast to previously studied Arrhenius photobases, NO₂-Acr-OH undergoes ESHID reactions in protic solvents as well as in polar aprotic solvents. Solvent-dependent photo-induced reactions of NO₂-Acr-OH are comprehensively studied by time-resolved fluorescence spectroscopy. Molecular designs for visible light triggered acridinol-based Arrhenius photobases with a large ΔpK_b value are proposed.

Original language	English
Pages (from-to)	668-673
Number of pages	6
Journal	New Journal of Chemistry
Volume	44
Issue number	3
DOIs	https://doi.org/10.1039/c9nj05404a
Publication status	Published - 2020

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Materials Chemistry

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@article{61c1343fc9464ca1b3d3845a5079cd50,

title = "A new visible light triggered Arrhenius photobase and its photo-induced reactions",

abstract = "Arrhenius photobases are of potential use for excited state hydroxide ion dissociation (ESHID), photo-induced pOH jump experiments, and base-catalyzed reactions. However, previously studied Arrhenius photobases have to be excited by UV light and undergo ESHID reactions only in protic solvents. These characteristics have become a disadvantage to their application in many fields of research. In this work, we have designed and synthesized a new Arrhenius photobase (NO2-Acr-OH), the ESHID reaction of which is readily triggered by visible light excitation. In contrast to previously studied Arrhenius photobases, NO2-Acr-OH undergoes ESHID reactions in protic solvents as well as in polar aprotic solvents. Solvent-dependent photo-induced reactions of NO2-Acr-OH are comprehensively studied by time-resolved fluorescence spectroscopy. Molecular designs for visible light triggered acridinol-based Arrhenius photobases with a large ΔpKb value are proposed.",

author = "Joung, {Joonyoung F.} and Jeeun Lee and Joungin Hwang and Kihang Choi and Sungnam Park",

note = "Funding Information: This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2019R1H1A2079968 and 2019R1A6A1A11044070 for S. P. and No. 20100020209 for K. C.). Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.",

year = "2020",

doi = "10.1039/c9nj05404a",

language = "English",

volume = "44",

pages = "668--673",

journal = "New Journal of Chemistry",

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publisher = "Royal Society of Chemistry",

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T1 - A new visible light triggered Arrhenius photobase and its photo-induced reactions

AU - Joung, Joonyoung F.

AU - Lee, Jeeun

AU - Hwang, Joungin

AU - Choi, Kihang

AU - Park, Sungnam

N1 - Funding Information: This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2019R1H1A2079968 and 2019R1A6A1A11044070 for S. P. and No. 20100020209 for K. C.). Publisher Copyright: This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

PY - 2020

Y1 - 2020

N2 - Arrhenius photobases are of potential use for excited state hydroxide ion dissociation (ESHID), photo-induced pOH jump experiments, and base-catalyzed reactions. However, previously studied Arrhenius photobases have to be excited by UV light and undergo ESHID reactions only in protic solvents. These characteristics have become a disadvantage to their application in many fields of research. In this work, we have designed and synthesized a new Arrhenius photobase (NO2-Acr-OH), the ESHID reaction of which is readily triggered by visible light excitation. In contrast to previously studied Arrhenius photobases, NO2-Acr-OH undergoes ESHID reactions in protic solvents as well as in polar aprotic solvents. Solvent-dependent photo-induced reactions of NO2-Acr-OH are comprehensively studied by time-resolved fluorescence spectroscopy. Molecular designs for visible light triggered acridinol-based Arrhenius photobases with a large ΔpKb value are proposed.

AB - Arrhenius photobases are of potential use for excited state hydroxide ion dissociation (ESHID), photo-induced pOH jump experiments, and base-catalyzed reactions. However, previously studied Arrhenius photobases have to be excited by UV light and undergo ESHID reactions only in protic solvents. These characteristics have become a disadvantage to their application in many fields of research. In this work, we have designed and synthesized a new Arrhenius photobase (NO2-Acr-OH), the ESHID reaction of which is readily triggered by visible light excitation. In contrast to previously studied Arrhenius photobases, NO2-Acr-OH undergoes ESHID reactions in protic solvents as well as in polar aprotic solvents. Solvent-dependent photo-induced reactions of NO2-Acr-OH are comprehensively studied by time-resolved fluorescence spectroscopy. Molecular designs for visible light triggered acridinol-based Arrhenius photobases with a large ΔpKb value are proposed.

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DO - 10.1039/c9nj05404a

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EP - 673

JO - New Journal of Chemistry

JF - New Journal of Chemistry

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ER -

A new visible light triggered Arrhenius photobase and its photo-induced reactions

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