Fluorescent anion sensor derived from cholic acid: The use of flexible side chain

Lei Fang; Wing Hong Chan; Yong Bing He; Daniel W.J. Kwong; Albert W.M. Lee

doi:10.1021/jo050913h

Fluorescent anion sensor derived from cholic acid: The use of flexible side chain

Lei Fang, Wing Hong Chan^*, Yong Bing He, Daniel W.J. Kwong, Albert W.M. Lee

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

46 Citations (Scopus)

Abstract

The fluorescent photoinduced electron transfer (PET) chemosensors 1-3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thiourea H-bond donating group. Comparative studies on their binding affinity toward carboxylates, dihydrogen phosphate, and halides revealed that the amidothiourea moiety on the C17 side chain could work cooperatively with H-bond donating groups on C7 and C12 to bind spherical halogen anions. An unexpected specific fluorescence enhancement of 1 by coordinating bromide ion was observed.

Original language	English
Pages (from-to)	7640-7646
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	70
Issue number	19
DOIs	https://doi.org/10.1021/jo050913h
Publication status	Published - 16 Sept 2005

Scopus Subject Areas

Organic Chemistry

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title = "Fluorescent anion sensor derived from cholic acid: The use of flexible side chain",

abstract = "The fluorescent photoinduced electron transfer (PET) chemosensors 1-3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thiourea H-bond donating group. Comparative studies on their binding affinity toward carboxylates, dihydrogen phosphate, and halides revealed that the amidothiourea moiety on the C17 side chain could work cooperatively with H-bond donating groups on C7 and C12 to bind spherical halogen anions. An unexpected specific fluorescence enhancement of 1 by coordinating bromide ion was observed.",

author = "Lei Fang and Chan, {Wing Hong} and He, {Yong Bing} and Kwong, {Daniel W.J.} and Lee, {Albert W.M.}",

note = "The work described in this article was fully supported by grants from the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE/P-10/01), and from the Hong Kong Baptist University (FRG/03-04/II-15). ",

year = "2005",

month = sep,

day = "16",

doi = "10.1021/jo050913h",

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T1 - Fluorescent anion sensor derived from cholic acid

T2 - The use of flexible side chain

AU - Fang, Lei

AU - Chan, Wing Hong

AU - He, Yong Bing

AU - Kwong, Daniel W.J.

AU - Lee, Albert W.M.

N1 - The work described in this article was fully supported by grants from the University Grants Committee of the Hong Kong Special Administrative Region, China (AoE/P-10/01), and from the Hong Kong Baptist University (FRG/03-04/II-15).

PY - 2005/9/16

Y1 - 2005/9/16

N2 - The fluorescent photoinduced electron transfer (PET) chemosensors 1-3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thiourea H-bond donating group. Comparative studies on their binding affinity toward carboxylates, dihydrogen phosphate, and halides revealed that the amidothiourea moiety on the C17 side chain could work cooperatively with H-bond donating groups on C7 and C12 to bind spherical halogen anions. An unexpected specific fluorescence enhancement of 1 by coordinating bromide ion was observed.

AB - The fluorescent photoinduced electron transfer (PET) chemosensors 1-3 were synthesized from cholic acid. 1 and 2 containing amidothiourea groups as anion receptive sites demonstrated much higher affinity toward anions than 3 containing traditional thiourea H-bond donating group. Comparative studies on their binding affinity toward carboxylates, dihydrogen phosphate, and halides revealed that the amidothiourea moiety on the C17 side chain could work cooperatively with H-bond donating groups on C7 and C12 to bind spherical halogen anions. An unexpected specific fluorescence enhancement of 1 by coordinating bromide ion was observed.

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U2 - 10.1021/jo050913h

DO - 10.1021/jo050913h

M3 - Journal article

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SN - 0022-3263

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EP - 7646

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Fluorescent anion sensor derived from cholic acid: The use of flexible side chain

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