Selective recognition of fluoride by using a benzobisimidazolium derivative through aggregation-induced fluorescence

Dayoung Lee; Chiho Lee; Eun Jin Jun; Minji Lee; Sungnam Park; Juyoung Yoon

doi:10.1002/open.201700109

Selective recognition of fluoride by using a benzobisimidazolium derivative through aggregation-induced fluorescence

Dayoung Lee, Chiho Lee, Eun Jin Jun, Minji Lee, Sungnam Park, Juyoung Yoon

Department of Chemistry & Nanoscience

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

8 Scopus citations

Abstract

A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F^– ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH₃CN) is significantly stronger with F^– and acetate (CH₃CO₂^–), but not with other anions (Cl^–, Br^–, I^–, HSO₄^–, and H₂PO₄^–). The fluorescence of 1 is enhanced selectively with F^– in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F^– play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F^– in CH₃CN is a key step for the selective sensing of F^–, and the fluorescence of the aggregates is further enhanced in a mixture of 95% CH₃CN and 5% water, which can be attributed to the aggregation-induced emission.

Original language	English
Pages (from-to)	476-479
Number of pages	4
Journal	ChemistryOpen
Volume	6
Issue number	4
DOIs	https://doi.org/10.1002/open.201700109
State	Published - Aug 2017

Bibliographical note

Funding Information:
This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.).

Funding Information:
This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.). Mass spectral data were obtained from the Korea Basic Science Institute (Daegu) on a Jeol JMS 700 high-resolution mass spectrometer.

Publisher Copyright:
© 2017 The Authors.

Keywords

Aggregation-induced emission
Chemosensors
Fluorescent probes
Fluoride
Imidazolium

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10.1002/open.201700109

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title = "Selective recognition of fluoride by using a benzobisimidazolium derivative through aggregation-induced fluorescence",

abstract = "A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F– ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH3CN) is significantly stronger with F– and acetate (CH3CO2–), but not with other anions (Cl–, Br–, I–, HSO4–, and H2PO4–). The fluorescence of 1 is enhanced selectively with F– in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F– play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F– in CH3CN is a key step for the selective sensing of F–, and the fluorescence of the aggregates is further enhanced in a mixture of 95% CH3CN and 5% water, which can be attributed to the aggregation-induced emission.",

keywords = "Aggregation-induced emission, Chemosensors, Fluorescent probes, Fluoride, Imidazolium",

author = "Dayoung Lee and Chiho Lee and Jun, {Eun Jin} and Minji Lee and Sungnam Park and Juyoung Yoon",

note = "Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.). Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.). Mass spectral data were obtained from the Korea Basic Science Institute (Daegu) on a Jeol JMS 700 high-resolution mass spectrometer. Publisher Copyright: {\textcopyright} 2017 The Authors.",

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AU - Lee, Dayoung

AU - Lee, Chiho

AU - Jun, Eun Jin

AU - Lee, Minji

AU - Park, Sungnam

AU - Yoon, Juyoung

N1 - Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.). Funding Information: This study was supported by a grant from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (2012R1A3A2048814 for J.Y.; 20100020209 for S.P.). Mass spectral data were obtained from the Korea Basic Science Institute (Daegu) on a Jeol JMS 700 high-resolution mass spectrometer. Publisher Copyright: © 2017 The Authors.

PY - 2017/8

Y1 - 2017/8

N2 - A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F– ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH3CN) is significantly stronger with F– and acetate (CH3CO2–), but not with other anions (Cl–, Br–, I–, HSO4–, and H2PO4–). The fluorescence of 1 is enhanced selectively with F– in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F– play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F– in CH3CN is a key step for the selective sensing of F–, and the fluorescence of the aggregates is further enhanced in a mixture of 95% CH3CN and 5% water, which can be attributed to the aggregation-induced emission.

AB - A new benzobisimidazolium derivative (1) bearing four naphthalene moieties was synthesized and demonstrated as an F– ion-selective fluorescent chemosensor. The fluorescence of 1 in acetonitrile (CH3CN) is significantly stronger with F– and acetate (CH3CO2–), but not with other anions (Cl–, Br–, I–, HSO4–, and H2PO4–). The fluorescence of 1 is enhanced selectively with F– in the presence of a small amount of water. Our DFT calculations indicate that the electrostatic interactions between the positively charged benzobisimidazolium moieties and F– play an important role in the formation of stable aggregates. The formation of stable aggregates of 1 with F– in CH3CN is a key step for the selective sensing of F–, and the fluorescence of the aggregates is further enhanced in a mixture of 95% CH3CN and 5% water, which can be attributed to the aggregation-induced emission.

KW - Aggregation-induced emission

KW - Chemosensors

KW - Fluorescent probes

KW - Fluoride

KW - Imidazolium

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ER -

Selective recognition of fluoride by using a benzobisimidazolium derivative through aggregation-induced fluorescence

Abstract

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Keywords

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