Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate

Shigehiro Sumiya; Takayuki Doi; Yasuhiro Shiraishi; Takayuki Hirai

doi:10.1016/j.tet.2011.10.097

Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate

Shigehiro Sumiya, Takayuki Doi, Yasuhiro Shiraishi, Takayuki Hirai

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

46 Citations (Scopus)

Abstract

A fluorescein-spiropyran conjugate (2) behaves as a receptor for colorimetric sensing of cyanide anion (CN^-) in aqueous media under irradiation of UV light. The compound 2, which exists as a spirocycle-closed (SP) form in the dark condition, is isomerized to the spirocycle-opened merocyanine (MC) form upon irradiation of UV light and shows absorption bands at 467 and 568 nm. Addition of CN^- to the solution leads to a decrease in these bands and an appearance of new absorption band at 512 nm, via a nucleophilic interaction between CN^- and the spirocarbon of MC form. This absorption change occurs selectively with CN^- and enables ratiometric quantification of CN^- by absorption analysis.

Original language	English
Pages (from-to)	690-696
Number of pages	7
Journal	Tetrahedron
Volume	68
Issue number	2
DOIs	https://doi.org/10.1016/j.tet.2011.10.097
Publication status	Published - 2012 Jan 14
Externally published	Yes

Keywords

Cyanide
Fluorescein
Receptor
Spiropyran
Water

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.10.097

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title = "Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate",

abstract = "A fluorescein-spiropyran conjugate (2) behaves as a receptor for colorimetric sensing of cyanide anion (CN-) in aqueous media under irradiation of UV light. The compound 2, which exists as a spirocycle-closed (SP) form in the dark condition, is isomerized to the spirocycle-opened merocyanine (MC) form upon irradiation of UV light and shows absorption bands at 467 and 568 nm. Addition of CN- to the solution leads to a decrease in these bands and an appearance of new absorption band at 512 nm, via a nucleophilic interaction between CN- and the spirocarbon of MC form. This absorption change occurs selectively with CN- and enables ratiometric quantification of CN- by absorption analysis.",

keywords = "Cyanide, Fluorescein, Receptor, Spiropyran, Water",

author = "Shigehiro Sumiya and Takayuki Doi and Yasuhiro Shiraishi and Takayuki Hirai",

note = "Funding Information: This work was supported by a Grant-in-Aids for Scientific Research (No. 21760619 ) from the Ministry of Education, Culture, Sports, Science and Technology , Japan (MEXT). S.S. thanks the Japan Society for Promotion of Science (JSPS) for Young Scientist and the Global COE Program {\textquoteleft}Global Education and Research Center for Bio-Environmental Chemistry{\textquoteright} of Osaka University. ",

year = "2012",

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doi = "10.1016/j.tet.2011.10.097",

language = "English",

volume = "68",

pages = "690--696",

journal = "Tetrahedron",

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T1 - Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate

AU - Sumiya, Shigehiro

AU - Doi, Takayuki

AU - Shiraishi, Yasuhiro

AU - Hirai, Takayuki

N1 - Funding Information: This work was supported by a Grant-in-Aids for Scientific Research (No. 21760619 ) from the Ministry of Education, Culture, Sports, Science and Technology , Japan (MEXT). S.S. thanks the Japan Society for Promotion of Science (JSPS) for Young Scientist and the Global COE Program ‘Global Education and Research Center for Bio-Environmental Chemistry’ of Osaka University.

PY - 2012/1/14

Y1 - 2012/1/14

N2 - A fluorescein-spiropyran conjugate (2) behaves as a receptor for colorimetric sensing of cyanide anion (CN-) in aqueous media under irradiation of UV light. The compound 2, which exists as a spirocycle-closed (SP) form in the dark condition, is isomerized to the spirocycle-opened merocyanine (MC) form upon irradiation of UV light and shows absorption bands at 467 and 568 nm. Addition of CN- to the solution leads to a decrease in these bands and an appearance of new absorption band at 512 nm, via a nucleophilic interaction between CN- and the spirocarbon of MC form. This absorption change occurs selectively with CN- and enables ratiometric quantification of CN- by absorption analysis.

AB - A fluorescein-spiropyran conjugate (2) behaves as a receptor for colorimetric sensing of cyanide anion (CN-) in aqueous media under irradiation of UV light. The compound 2, which exists as a spirocycle-closed (SP) form in the dark condition, is isomerized to the spirocycle-opened merocyanine (MC) form upon irradiation of UV light and shows absorption bands at 467 and 568 nm. Addition of CN- to the solution leads to a decrease in these bands and an appearance of new absorption band at 512 nm, via a nucleophilic interaction between CN- and the spirocarbon of MC form. This absorption change occurs selectively with CN- and enables ratiometric quantification of CN- by absorption analysis.

KW - Cyanide

KW - Fluorescein

KW - Receptor

KW - Spiropyran

KW - Water

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 2

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Colorimetric sensing of cyanide anion in aqueous media with a fluorescein-spiropyran conjugate

Abstract

Keywords

ASJC Scopus subject areas

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