A series of bishydrazide compounds
have been developed for selective
turn-on detection of Al3+ cation, based on metal chelation-enhanced
fluorescence (CHEF) effects that inhibit the nonradiative PET and
ESIPT processes. In aqueous solution, Al3+ selectively
induces strong fluorescence of these compounds with large Stokes shifts
up to ∼133 nm and emission colors varying from blue to orange.
In the solid phase, both Al3+ and Zn2+ give
apparent fluorescence which is simultaneously detected based on chromatographic
separation.
Glucopyranosyl-1,4-dihydropyridine (Glc-DHP) was synthesized as a new fluorescent chemosensor via cyclotrimerization of the β-amino acrylate in the presence of TiCl4. This DHP derivative is soluble in aqueous medium and the solution gives a blue fluorescence signal with a quantum yield of 29%. The fluorescence signal of Glc-DHP was selectively quenched by 2,4,6-trinitrophenol (TNP) with a quenching coefficient (Ksv) of 4.47 × 10(4) and at one of the best reported detection limits of 0.94 μM. The quenching mechanism was confirmed to be of the static type at the low concentration region (less than 50 μM) with the significant quenching effect of competitive absorption starting from the concentration of 50 μM. Even in the real sample (seawater and industrial water), the quenching efficiencies of TNP on the fluorescence emission of Glc-DHP were proven to be at the same level with that of the test in pure water, demonstrating the practicability of the detection. Furthermore, a fluorescent paper sensor could be prepared by immersing the paper into the Glc-DHP solution. The fluorescence of the paper sensor disappeared either by writing with TNP solution or by exposure to TNP vapor. This detection could be observed by the naked eye under black light. The pH effect was proven to be a substantial factor in the quenching mechanism, providing an accurate determination of TNP, 2,4-dinitrophenol (DNP) and 4-nitrophenol (4NP) in real mixed-samples.
The upper-rim of calix[4]arene is modified with phenylacetylene derivatives via Sonogashira coupling reaction to produce a wider cavity for entrapping TNT.
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