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• W2105386157 abstract "Molecular hybrids of TQEN (N,N,N′,N′-tetrakis(2-quinolylmethyl)ethylenediamine) and EDTA (ethylenediamine-N,N,N′,N′-tetraacetic acid) were examined as fluorescent Zn2+ sensors. Upon the addition of Zn2+, N,N-BQENDA (N,N-bis(2-quinolylmethyl)ethylenediamine-N′,N′-diacetic acid, 1a) exhibits a 30-fold emission enhancement at 456 nm (λex = 315 nm, ϕZn = 0.018) in buffer (HEPES, pH = 7.5, 100 mM KCl). The fluorescence enhancement is Zn2+-specific as Cd2+ induces much smaller increases (ICd/I0 = 5 and ICd/IZn = 16%). These spectroscopic properties, as well as the excellent water-solubility, represent a significant improvement compared to the parent TQEN sensor (ϕZn = 0.007, ICd/IZn = 64%). The isoquinoline analog N,N-1-isoBQENDA (N,N-bis(1-isoquinolylmethyl)ethylenediamine-N′,N′-diacetic acid, 1b) possesses a similar Zn2+ fluorescence response to the parent 1-isoTQEN (N,N,N′,N′-tetrakis(1-isoquinolylmethyl)ethylenediamine) sensor, but exhibits diminished fluorescence intensity. Apo 1a and 1b extract more than 50% of the Zn2+ from an equimolar amount of [Zn(TPEN)]2+ (TPEN = N,N,N′,N′-tetrakis(2-pyridylmethyl)ethylenediamine) or [Zn(EDTA)]2−, whereas TPEN and EDTA cannot effectively remove Zn2+ from [Zn(1a)] and [Zn(1b)]. The reduction of steric crowding in [Zn(TQEN)]2+ resulting from the substitution of two quinolines with carboxylates enhances the interaction between the metal ion and the remaining quinoline nitrogen atoms. The stronger bonding interaction results in enhanced emission intensity, Zn2+ selectivity and metal ion affinity. This is in contrast to [Zn(1-isoTQEN)]2+ where the isoquinoline-carboxylate replacement does not relieve any coordination distortion, therefore no significant changes in fluorescence or metal binding properties are observed." @default.
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• W2105386157 date "2014-01-01" @default.
• W2105386157 modified "2023-10-17" @default.
• W2105386157 title "Bis(2-quinolylmethyl)ethylenediaminediacetic acids (BQENDAs), TQEN–EDTA hybrid molecules as fluorescent zinc sensors" @default.
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• W2105386157 doi "https://doi.org/10.1039/c4dt00261j" @default.
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