Fluorescent anion sensor derived from cholic acid: the use of flexible side chain |
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Authors: | Fang Lei Chan Wing-Hong He Yong-Bing Kwong Daniel W J Lee Albert W M |
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Institution: | Department of Chemistry and Central Laboratory of the Institute of Molecular Technology for Drug Discovery and Synthesis, Hong Kong Baptist University, Hong Kong SAR, PR China. |
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Abstract: | structure: see text] 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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