2005
DOI: 10.1021/ol0473445
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Ratiometric and Selective Fluorescent Sensor for CuIIBased on Internal Charge Transfer (ICT)

Abstract: A Cu(II)-sensing, ratiometric, and selective fluorescent sensor 1, N-butyl-4,5-di[(pyridin-2-ylmethyl)amino]-1,8-naphthalimide, was designed and synthesized on the basis of the mechanism of internal charge transfer (ICT). In aqueous ethanol solutions of 1, the presence of Cu(II) induces the formation of a 1:1 metal-ligand complex, which exhibits a strong, increasing fluorescent emission centered at 475 nm at the expense of the fluorescent emission of 1 centered at 525 nm. [structure: see text]

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Cited by 524 publications
(210 citation statements)
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“…At the same time, the perceived color change would make the rapid visual sensing possible and bring higher sensitivity. (13,14) Although many successful approaches to fl uorescent sensing of Zn 2+ have been reported, (11, few have the ability of a ratiometric fl uorescent response to Zn 2+ . (11,(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35) Furthermore, most of these ratiometric fl uorescent probes for Zn 2+ suff er from shortcomings, such as low water solubility, disturbance from Cd 2+ , large fl uorescence increase or decrease in the Zn 2+ -bound form.…”
Section: Introductionmentioning
confidence: 99%
“…At the same time, the perceived color change would make the rapid visual sensing possible and bring higher sensitivity. (13,14) Although many successful approaches to fl uorescent sensing of Zn 2+ have been reported, (11, few have the ability of a ratiometric fl uorescent response to Zn 2+ . (11,(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35) Furthermore, most of these ratiometric fl uorescent probes for Zn 2+ suff er from shortcomings, such as low water solubility, disturbance from Cd 2+ , large fl uorescence increase or decrease in the Zn 2+ -bound form.…”
Section: Introductionmentioning
confidence: 99%
“…3), which shows a blue shift of about 47 nm compared to the 1,8-naphthalimide analogues. [26] Such a blue-shift was also observed in the emission spectra of SC encapsulated APTES/SBA-15 [25] and interpreted in terms of the molecular orbital confinement theory, that all energy levels of guest molecules increase in the channel of the host as a result of the confinement. [27] In our hybrid material the increase in the energy level of the P2 molecule probably results in the blue shift on the spectrum of SBA-P2.…”
Section: Binding Abilities Of the Functionalized Materials Sba-p2 Withmentioning
confidence: 75%
“…These bands can be attributed to the typical electronic transition of the aromatic ring. [26] FT-IR spectra of SBA-P2 (see Supporting Information, Fig. S3) exhibited several new bands at about 2 923, 2 860, and 1 366 cm À1 , assignable to aliphatic CÀH stretching vibrations attributed to pendant, NÀH stretching vibrations of the imine groups and C¼C stretching vibrations of 1,8-naphthalimide attached SBA-15, respectively.…”
Section: Synthesis and Characterization Of The Functionalized Materiamentioning
confidence: 99%
“…Recently, naphthalimide-based probes for various cations via chromogenical and fluorogenical signals have received increasing interests such as Hg 2+ , 30 Zn 2+ , 31 Cu 2+ , 32 and Ag + . 33 However, only a few fiber-optic fluorescence sensors based on naphthalimide derivatives have been developed.…”
Section: Introductionmentioning
confidence: 99%