Chiral discrimination in the fluorescence quenching of pyrene complexed to β-cyclodextrin

Hong Yang; Cornelia Bohne

doi:10.1016/1010-6030(94)03940-V

Chiral discrimination in the fluorescence quenching of pyrene complexed to β-cyclodextrin

Hong Yang, Cornelia Bohne

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

Abstract

Chiral discrimination was observed for the quenching by d- and l-tryptophan of excited singlet pyrene when complexed to β-CD in the presence of alcohols or short chain alkyl sulfates. Alcohols or alkyl sulfates were added to increase the association constant of pyrene with β-cyclodextrin. In all cases the quenching by d-tryptophan is more efficient than for l-tryptophan. The largest discrimination was observed in the presence of tert-butanol (K_sv(d)/K_sv(l)) = 3.6) owing to a marked decrease of the quenching efficiency by l-tryptophan. Quenching occurs through a static mechanism indicating that pyrene and tryptophan are in close proximity within the cyclodextrin complex.

Original language	English (US)
Pages (from-to)	209-217
Number of pages	9
Journal	Journal of Photochemistry and Photobiology, A: Chemistry
Volume	86
Issue number	1-3
DOIs	https://doi.org/10.1016/1010-6030(94)03940-V
State	Published - Feb 15 1995
Externally published	Yes

Keywords

Chiral discrimination
Fluorescence quenching
Pyrene
β-Cyclodextrin

ASJC Scopus subject areas

General Chemistry
General Chemical Engineering
General Physics and Astronomy

Online availability

10.1016/1010-6030(94)03940-V

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title = "Chiral discrimination in the fluorescence quenching of pyrene complexed to β-cyclodextrin",

abstract = "Chiral discrimination was observed for the quenching by d- and l-tryptophan of excited singlet pyrene when complexed to β-CD in the presence of alcohols or short chain alkyl sulfates. Alcohols or alkyl sulfates were added to increase the association constant of pyrene with β-cyclodextrin. In all cases the quenching by d-tryptophan is more efficient than for l-tryptophan. The largest discrimination was observed in the presence of tert-butanol (Ksv(d)/Ksv(l)) = 3.6) owing to a marked decrease of the quenching efficiency by l-tryptophan. Quenching occurs through a static mechanism indicating that pyrene and tryptophan are in close proximity within the cyclodextrin complex.",

keywords = "Chiral discrimination, Fluorescence quenching, Pyrene, β-Cyclodextrin",

author = "Hong Yang and Cornelia Bohne",

note = "Funding Information: This research was supported by the Natural Sciences and Engineering Research Council of Canada. The University of Victoria is also gratefully acknowledged for providing set up funds.",

year = "1995",

month = feb,

day = "15",

doi = "10.1016/1010-6030(94)03940-V",

language = "English (US)",

volume = "86",

pages = "209--217",

journal = "Journal of Photochemistry and Photobiology, A: Chemistry",

issn = "1010-6030",

publisher = "Elsevier B.V.",

number = "1-3",

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TY - JOUR

T1 - Chiral discrimination in the fluorescence quenching of pyrene complexed to β-cyclodextrin

AU - Yang, Hong

AU - Bohne, Cornelia

N1 - Funding Information: This research was supported by the Natural Sciences and Engineering Research Council of Canada. The University of Victoria is also gratefully acknowledged for providing set up funds.

PY - 1995/2/15

Y1 - 1995/2/15

N2 - Chiral discrimination was observed for the quenching by d- and l-tryptophan of excited singlet pyrene when complexed to β-CD in the presence of alcohols or short chain alkyl sulfates. Alcohols or alkyl sulfates were added to increase the association constant of pyrene with β-cyclodextrin. In all cases the quenching by d-tryptophan is more efficient than for l-tryptophan. The largest discrimination was observed in the presence of tert-butanol (Ksv(d)/Ksv(l)) = 3.6) owing to a marked decrease of the quenching efficiency by l-tryptophan. Quenching occurs through a static mechanism indicating that pyrene and tryptophan are in close proximity within the cyclodextrin complex.

AB - Chiral discrimination was observed for the quenching by d- and l-tryptophan of excited singlet pyrene when complexed to β-CD in the presence of alcohols or short chain alkyl sulfates. Alcohols or alkyl sulfates were added to increase the association constant of pyrene with β-cyclodextrin. In all cases the quenching by d-tryptophan is more efficient than for l-tryptophan. The largest discrimination was observed in the presence of tert-butanol (Ksv(d)/Ksv(l)) = 3.6) owing to a marked decrease of the quenching efficiency by l-tryptophan. Quenching occurs through a static mechanism indicating that pyrene and tryptophan are in close proximity within the cyclodextrin complex.

KW - Chiral discrimination

KW - Fluorescence quenching

KW - Pyrene

KW - β-Cyclodextrin

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JO - Journal of Photochemistry and Photobiology, A: Chemistry

JF - Journal of Photochemistry and Photobiology, A: Chemistry

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Chiral discrimination in the fluorescence quenching of pyrene complexed to β-cyclodextrin

Abstract

Keywords

ASJC Scopus subject areas

Online availability

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