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

Research output: Contribution to journalArticlepeer-review

43 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 languageEnglish
Pages (from-to)7640-7646
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number19
DOIs
Publication statusPublished - 16 Sep 2005

Scopus Subject Areas

  • Organic Chemistry

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