A Fluorescent Sensor with High Selectivity and Sensitivity for Potassium in Water

He, Hong; Mortellaro, Mark A.; Leiner, Marc J. P.; Fraatz, Robert J.; Tusa, James K.

doi:10.1021/ja0284761

Cited by 309 publications

(198 citation statements)

References 13 publications

Supporting

Mentioning

188

Contrasting

Unclassified

Order By: Relevance

“…2A) from TAC-aldehyde was reported previously (16). Synthesis of the K ϩ -binding TACaldehyde involves 17 steps (17). Conjugation of TAC-LimeDiSE with amino dextran (10 kDa; Molecular Probes, 4 mol free amine/mol dextran) was accomplished by reacting for 12 h three molar equivalents of TAC-Lime-DiSE with 1 molar equivalent amino dextran in an aqueous solution buffered at pH 7.4.…”

Section: Synthesis Of Dextran-conjugated Fluorescent Kmentioning

confidence: 99%

In Situ Measurement of Airway Surface Liquid [K+] Using a Ratioable K+-sensitive Fluorescent Dye

Namkung

Song

Mills

et al. 2009

Journal of Biological Chemistry

View full text Add to dashboard Cite

Section: Synthesis Of Dextran-conjugated Fluorescent Kmentioning

confidence: 99%

In Situ Measurement of Airway Surface Liquid [K+] Using a Ratioable K+-sensitive Fluorescent Dye

Namkung

Song

Mills

et al. 2009

Journal of Biological Chemistry

View full text Add to dashboard Cite

“…[26][27][28][29][30][31][32][33][34][35][36][37] Others have even found commercial success in blood electrolyte diagnostics. [38][39][40][41] Beside convenient synthetic routes, these compounds have very useful optical and redox properties which lead to the above applications. Compound 1 2 is a well-behaved fluorescent PET (photoinduced electron transfer) system [42][43][44][45] of the 'fluorophorespacer-receptor' format, 46,47 whose fluorescence responds sharply to H + .…”

Section: Introductionmentioning

confidence: 99%

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

Zheng

Lynch

Rice

et al. 2012

Photochem Photobiol Sci

View full text Add to dashboard Cite

Naphthalenic compounds are a rich resource for designers of fluorescent sensing/switching/logic systems. The degree of internal charge transfer (ICT) character in the fluorophore excited states can vary from negligible to substantial. 8;4,, 1,8-naphthalimides ( 16) and 4-chloro-1,8-naphthalimides (15) are of the former type. The latter type is represented by the 4-alkylamino-1,8-naphthalimides (1). Whether ICT-based or not, these serve as the fluorophore in 'fluorophore-spacerreceptor' switching systems where PET holds sway until the receptor is bound to H + . On the other hand, 4-dialkylamino-1,8-naphthalimides (3-4) show modest H + -induced fluorescence switching unless the 4-dialkylamino group is a part of a small ring (5). Electrostatic destabilization of a non-emissive twisted internal charge transfer (ICT) excited state is the origin of this behaviour. An evolution to the nonemissive twisted ICT excited state is responsible for the weak emission of the model compound 6 (and related structures 7 and 8) across the pH range. Twisted ICT excited states are also implicated in the switch 9 and its model compound 10, which are based on the 6-dialkylamino-3H-benzimidazo[2,1-a]benz [d,e]isoquinolin-3-one fluorophore. † Dedicated to Jean-Pierre Desvergne and to Hubert Le Bozec. ‡ This article is published as part of a themed issue in honour of Jean-Pierre Desvergne on the occasion of his 65th birthday.

show abstract

“…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

View full text Add to dashboard Cite

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.

show abstract

A Fluorescent Sensor with High Selectivity and Sensitivity for Potassium in Water

Cited by 309 publications

References 13 publications

In Situ Measurement of Airway Surface Liquid [K+] Using a Ratioable K+-sensitive Fluorescent Dye

In Situ Measurement of Airway Surface Liquid [K+] Using a Ratioable K+-sensitive Fluorescent Dye

Structural effects on the pH-dependent fluorescence of naphthalenic derivatives and consequences for sensing/switching

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

Contact Info

Product

Resources

About