Imaging Science and Photochemistry ›› 2017, Vol. 35 ›› Issue (4): 526-535.DOI: 10.7517/j.issn.1674-0475.2017.04.014

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Flavone-based ESIPT Fluorescent Probe for Determination of Triphenylphosphine

ZHANG Jian, LÜ Minghuan, ZHANG Weijuan, ZHAO Weili   

  1. Key Laboratory for Special Functional Materials of the Ministry of Education, Henan University, Kaifeng 475004, Henan, P. R. China
  • Received:2017-05-29 Revised:2017-06-09 Online:2017-07-15 Published:2017-07-15


Triphenylphosphine is an important organic substance with nucleophilicity and reducing character for a lone pair of electrons on phosphine. Nowadays it has been widely used in the synthesis of organic and organometallic compounds, such as Wittig reaction, Mitsunobu reaction, Appel reaction and Staudinger reaction. The massive use of PPh3 is unavoidable to cause phosphorous pollution into the environment that would pose potential threat to human health. An effective and convenient detection method of PPh3 is fairly urgent. At present, small-molecule fluorescence probes, due to their high sensitivity, concise detection procedure and easy-to-manipulate detection facility, have been recognized as one of the most attractive method to monitor and visualize analytes. Here a new Flavone-based turn-on fluorescent probe was constructed for detecting triphenylphosphine through the Staudinger ligation. The design concept was to use a 2-azidophenylacetic ester of a hydroxyl-containing fluorophore to react with PPh3 to undergo a rapid intramolecular acyl transfer through aza-ylide intermediate to release the fluorophore after hydrolysis, which showed high selectivity and sensitivity to the detection of PPh3 over other compounds in the dilute solution as well as in filter papers. The simple probe is potentially useful for qualitative and quantitative analysis of PPh3.

Key words: flavone, fluorescent probe, ESIPT, triphenylphosphine, Staudinger ligation