Ratiometry of monomer/excimer emissions of dipyrenyl calix[4]arene in aqueous media

Hyun Jung Kim; Duong Tuan Quang; Jooyeon Hong; Guipeun Kang; Sihyun Ham; Jong Seung Kim

doi:10.1016/j.tet.2007.05.130

Ratiometry of monomer/excimer emissions of dipyrenyl calix[4]arene in aqueous media

Hyun Jung Kim, Duong Tuan Quang, Jooyeon Hong, Guipeun Kang, Sihyun Ham, Jong Seung Kim

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

19 Citations (Scopus)

Abstract

Variations in the ratio of monomer/excimer emissions from pyrenyl groups bound to a calix[4]arene through facing carboxamidomethyl substituents have been investigated in H₂O/CH₃CN mixtures. Above a level of 50% H₂O, monomer emission declines and the excimer emission concomitantly increases. DFT calculations support the argument that disruption of intramolecular NHO bonds by water results in a geometry, which favors contact of the pyrene units and thus a strong excimer emission. Addition of Fe(III) to a H₂O/CH₃CN (4:1, v/v) solution of 1 at pH 6.1 quenches both monomer and excimer emissions through electron transfer (eT) from excited pyrene to the metal ion.

Original language	English
Pages (from-to)	10788-10792
Number of pages	5
Journal	Tetrahedron
Volume	63
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2007.05.130
Publication status	Published - 2007 Oct 29

Bibliographical note

Funding Information:
This work was supported by the SRC Research centre for Women's Diseases of Sookmyung Women's University.

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.05.130

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title = "Ratiometry of monomer/excimer emissions of dipyrenyl calix[4]arene in aqueous media",

abstract = "Variations in the ratio of monomer/excimer emissions from pyrenyl groups bound to a calix[4]arene through facing carboxamidomethyl substituents have been investigated in H2O/CH3CN mixtures. Above a level of 50% H2O, monomer emission declines and the excimer emission concomitantly increases. DFT calculations support the argument that disruption of intramolecular NHO bonds by water results in a geometry, which favors contact of the pyrene units and thus a strong excimer emission. Addition of Fe(III) to a H2O/CH3CN (4:1, v/v) solution of 1 at pH 6.1 quenches both monomer and excimer emissions through electron transfer (eT) from excited pyrene to the metal ion.",

author = "Kim, {Hyun Jung} and Quang, {Duong Tuan} and Jooyeon Hong and Guipeun Kang and Sihyun Ham and Kim, {Jong Seung}",

note = "Funding Information: This work was supported by the SRC Research centre for Women's Diseases of Sookmyung Women's University. ",

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T1 - Ratiometry of monomer/excimer emissions of dipyrenyl calix[4]arene in aqueous media

AU - Kim, Hyun Jung

AU - Quang, Duong Tuan

AU - Hong, Jooyeon

AU - Kang, Guipeun

AU - Ham, Sihyun

AU - Kim, Jong Seung

N1 - Funding Information: This work was supported by the SRC Research centre for Women's Diseases of Sookmyung Women's University.

PY - 2007/10/29

Y1 - 2007/10/29

N2 - Variations in the ratio of monomer/excimer emissions from pyrenyl groups bound to a calix[4]arene through facing carboxamidomethyl substituents have been investigated in H2O/CH3CN mixtures. Above a level of 50% H2O, monomer emission declines and the excimer emission concomitantly increases. DFT calculations support the argument that disruption of intramolecular NHO bonds by water results in a geometry, which favors contact of the pyrene units and thus a strong excimer emission. Addition of Fe(III) to a H2O/CH3CN (4:1, v/v) solution of 1 at pH 6.1 quenches both monomer and excimer emissions through electron transfer (eT) from excited pyrene to the metal ion.

AB - Variations in the ratio of monomer/excimer emissions from pyrenyl groups bound to a calix[4]arene through facing carboxamidomethyl substituents have been investigated in H2O/CH3CN mixtures. Above a level of 50% H2O, monomer emission declines and the excimer emission concomitantly increases. DFT calculations support the argument that disruption of intramolecular NHO bonds by water results in a geometry, which favors contact of the pyrene units and thus a strong excimer emission. Addition of Fe(III) to a H2O/CH3CN (4:1, v/v) solution of 1 at pH 6.1 quenches both monomer and excimer emissions through electron transfer (eT) from excited pyrene to the metal ion.

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DO - 10.1016/j.tet.2007.05.130

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Ratiometry of monomer/excimer emissions of dipyrenyl calix[4]arene in aqueous media

Abstract

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