A new bis-pyrene derivative as a selective colorimetric and fluorescent chemosensor for cyanide and fluoride and anion-activated CO2 sensing

Minji Lee; Jong Hun Moon; K. M.K. Swamy; Youngsuk Jeong; Gyoungmi Kim; Jiyoung Choi; Jin Yong Lee; Juyoung Yoon

doi:10.1016/j.snb.2014.04.005

A new bis-pyrene derivative as a selective colorimetric and fluorescent chemosensor for cyanide and fluoride and anion-activated CO₂ sensing

Minji Lee, Jong Hun Moon, K. M.K. Swamy, Youngsuk Jeong, Gyoungmi Kim, Jiyoung Choi, Jin Yong Lee, Juyoung Yoon

Department of Chemistry & Nanoscience

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

77 Scopus citations

Abstract

In the present study, we report the solvent controlled selectivity of cyanide. A newly synthesized bis-pyrene derivative 1 exhibited large "off-on" fluorescence enhancement with fluoride and cyanide in CH ₃CN-DMSO (99:1, v/v), which was accompanied by unique colorimetric changes. Likewise, in CH₃CN-DMSO-EtOH (98:1:1, v/v) or CH ₃CN-DMSO-H₂O (94:1:5, v/v), selective fluorescence enhancement with cyanide was observed among the various anions, which was attributed to a favourable interaction between the fluoride ion with ethanol or water. The binding modes, UV absorption and fluorescence changes of 1 upon CN^- binding are also explained by DFT calculations. Probe 1 was successfully applied for imaging cyanide in the HeLa cells. Finally, anion-activated CO₂ sensing via colour and fluorescence changes is demonstrated using chemosensor 1.

Original language	English
Pages (from-to)	369-376
Number of pages	8
Journal	Sensors and Actuators, B: Chemical
Volume	199
DOIs	https://doi.org/10.1016/j.snb.2014.04.005
State	Published - Aug 2014

Bibliographical note

Funding Information:
This work was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korea Government (MSIP) (No. 2012R1A3A2048814 ). The work at Sungkyunkwan University was supported by an NRF Grant ( 2007-0056343 ) funded by MEST.

Keywords

Anion recognition
Colorimetric sensor
Cyanide selective chemosensor
Fluorescence sensor

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10.1016/j.snb.2014.04.005

Cite this

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title = "A new bis-pyrene derivative as a selective colorimetric and fluorescent chemosensor for cyanide and fluoride and anion-activated CO2 sensing",

abstract = "In the present study, we report the solvent controlled selectivity of cyanide. A newly synthesized bis-pyrene derivative 1 exhibited large {"}off-on{"} fluorescence enhancement with fluoride and cyanide in CH 3CN-DMSO (99:1, v/v), which was accompanied by unique colorimetric changes. Likewise, in CH3CN-DMSO-EtOH (98:1:1, v/v) or CH 3CN-DMSO-H2O (94:1:5, v/v), selective fluorescence enhancement with cyanide was observed among the various anions, which was attributed to a favourable interaction between the fluoride ion with ethanol or water. The binding modes, UV absorption and fluorescence changes of 1 upon CN- binding are also explained by DFT calculations. Probe 1 was successfully applied for imaging cyanide in the HeLa cells. Finally, anion-activated CO2 sensing via colour and fluorescence changes is demonstrated using chemosensor 1.",

keywords = "Anion recognition, Colorimetric sensor, Cyanide selective chemosensor, Fluorescence sensor",

author = "Minji Lee and Moon, {Jong Hun} and Swamy, {K. M.K.} and Youngsuk Jeong and Gyoungmi Kim and Jiyoung Choi and Lee, {Jin Yong} and Juyoung Yoon",

note = "Funding Information: This work was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korea Government (MSIP) (No. 2012R1A3A2048814 ). The work at Sungkyunkwan University was supported by an NRF Grant ( 2007-0056343 ) funded by MEST. ",

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doi = "10.1016/j.snb.2014.04.005",

language = "English",

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AU - Lee, Minji

AU - Moon, Jong Hun

AU - Swamy, K. M.K.

AU - Jeong, Youngsuk

AU - Kim, Gyoungmi

AU - Choi, Jiyoung

AU - Lee, Jin Yong

AU - Yoon, Juyoung

N1 - Funding Information: This work was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korea Government (MSIP) (No. 2012R1A3A2048814 ). The work at Sungkyunkwan University was supported by an NRF Grant ( 2007-0056343 ) funded by MEST.

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N2 - In the present study, we report the solvent controlled selectivity of cyanide. A newly synthesized bis-pyrene derivative 1 exhibited large "off-on" fluorescence enhancement with fluoride and cyanide in CH 3CN-DMSO (99:1, v/v), which was accompanied by unique colorimetric changes. Likewise, in CH3CN-DMSO-EtOH (98:1:1, v/v) or CH 3CN-DMSO-H2O (94:1:5, v/v), selective fluorescence enhancement with cyanide was observed among the various anions, which was attributed to a favourable interaction between the fluoride ion with ethanol or water. The binding modes, UV absorption and fluorescence changes of 1 upon CN- binding are also explained by DFT calculations. Probe 1 was successfully applied for imaging cyanide in the HeLa cells. Finally, anion-activated CO2 sensing via colour and fluorescence changes is demonstrated using chemosensor 1.

AB - In the present study, we report the solvent controlled selectivity of cyanide. A newly synthesized bis-pyrene derivative 1 exhibited large "off-on" fluorescence enhancement with fluoride and cyanide in CH 3CN-DMSO (99:1, v/v), which was accompanied by unique colorimetric changes. Likewise, in CH3CN-DMSO-EtOH (98:1:1, v/v) or CH 3CN-DMSO-H2O (94:1:5, v/v), selective fluorescence enhancement with cyanide was observed among the various anions, which was attributed to a favourable interaction between the fluoride ion with ethanol or water. The binding modes, UV absorption and fluorescence changes of 1 upon CN- binding are also explained by DFT calculations. Probe 1 was successfully applied for imaging cyanide in the HeLa cells. Finally, anion-activated CO2 sensing via colour and fluorescence changes is demonstrated using chemosensor 1.

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KW - Fluorescence sensor

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