A fluorescent sensor for Cu2+ at the sub-ppm level

Mitchell, Kerry A.; Brown, Robert G.; Yuan, Dongwu; Chang, Shao-Chieh; Utecht, Ronald E.; Lewis, David E.

doi:10.1016/s1010-6030(97)00335-3

Cited by 91 publications

(33 citation statements)

References 10 publications

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“…Because of their overall high fluorescence quantum yields and photostability, they are considered good candidates for dye lasers. Also the use of 1,8-naphthalimide derivatives as DNA intercalators [22] and in quantization of paramagnetic transition metal cations by fluorescent emission enhancement were reported [23].…”

Section: Introductionmentioning

confidence: 99%

The synthesis and spectroscopic properties of novel, functional fluorescent naphthalimide dyes

Bardajee

Haley

et al. 2008

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

The synthesis and spectroscopic properties of novel, functional fluorescent naphthalimide dyes

Bardajee

Haley

et al. 2008

Dyes and Pigments

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“…This issue takes on added significance given the growing body of sensors and other optical devices which employ 4-amino-1,8-naphthalimide (or closely related) fluorophores. [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] Hence, compounds 1-3 and 4-6 were synthesized and tested by steady-state electronic absorption and emission spectroscopy. …”

Section: Introductionmentioning

confidence: 99%

The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides

Silva¹,

Goligher²,

Gunaratne³

et al. 2003

Arkivoc

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Regioselective photoinduced electron transfer (PET) has been previously observed in aminoalkyl-4-amino-1,8-naphthalimide 'fluorophore-spacer-receptor' systems. PET from the amine to the fluorophore was only observed when the electron entered the fluorophore in the region of its 4-NH group. This has received two related but distinct explanations. The first is a directing effect of the molecular-scale electric field of internal charge transfer (ICT) excited state of the fluorophore. The second is a peculiarity of 4-amino-1,8-naphthalimides in possessing a node at the imide nitrogen in its frontier orbitals. The six isomeric pyridylmethyl-4-amino-1,8-naphthalimides 1-3 and 4-6 are configured as 'fluorophore-spacer-receptor' systems in order to test the relative importance of these two explanations. The two regioisomeric sets are designed such that PET is thermodynamically feasible when they are protonated, which should lead to fluorescence quenching by protons. In practice, the proton-induced fluorescence quenching is moderate and more clearly observed in the set 1-3. This evidence points to the PET-accelerating effect of the molecular-scale electric field being mitigated by the presence of the node at the imide nitrogen in the frontier orbitals. Compound 4 also shows this proton-induced fluorescence quenching effect but to a still smaller extent. In this instance, the PET is hampered by the electric field alone. Compounds 5 and 6 show an excited state intramolecular proton transfer (ESIPT) involving water-mediated hydrogen-bonded rings, which dominates over any residual PET to produce proton-induced fluorescence enhancement. Again, the effect is moderate. The two mechanisms of PET regioselectivity can now be understood to operate additively in the aminoalkyl-4-amino-1,8-naphthalimides and subtractively in the protonated pyridylmethyl-4-amino-1,8-naphthalimides.

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“…We selected 4-amino-1,8-naphthalimide as the reporting group due to the desirable spectroscopic properties [11] and incorporated the bis(2-pyridylmethyl)amine (DPA) moiety into NIDPA for chelating zinc which can control Zn 2+ selectivity in aqueous media and neutral working pH [8,9]. On the other hand, the best spacer length between the receptor and fluorophore is a one or two-carbon linker, which can induce the process of PET.…”

Section: Design and Synthesis Of The Nidpamentioning

confidence: 99%

“…Consequently, the detection of Zn 2+ with low concentration in vivo has attracted increasing interests. Many fluorescent sensors that can selectively detect Zn 2+ have been reported in the past few years [7][8][9][10][11], and most of them involve the principle of photo-induced electron transfer (PET) in the signaling process. However, there is still scope for improvement in the design of such sensors as they often suffer from disadvantages such as sensitivity to H + , Ca 2+ and Mg 2+ , short excitation and emission wavelengths, small Stokes shifts and cumbersome synthesis.…”

Section: Introductionmentioning

confidence: 99%