- Synthesis and spectroscopic characterization of a fluorescent phenanthrene-rhodamine dyad for ratiometric measurements of acid pH values
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We present the rational design, synthesis and spectroscopic characterization of a novel dual excitation, three color emitting, pH-responsive fluorescent probe consisting of two phenanthrene and one rhodamine B units linked by click chemistry. The rhodamine moiety, excitable atλEx= 315 nm and atλEx= 560 nm in its ring-opened form, provides the pH-responsive fluorophore, while the pH-insensitive phenanthrene, excited atλEx= 315 nm, serves as inert internal reference, The presence of two phenanthrene moieties enables a blue monomer and a blueish green excimer emission at 351 nm and 500 nm, respectively. Opening of the rhodamine B spirolactam ring at an acidic pH below 5.0 (pKa= 2.59 ± 0.04) switches on its emission at 580 nm. Simultaneously, the phenanthrene excimer emission decreases caused by a change in orientation of the phenanthrene units, while the monomer emission is barely affected. This sensor design enables ratiometric measurements in the low acidic pH range utilizing the intensity ratios of the rhodamine B and phenanthrene excimer emission at 580 nm and 500 nm. Alternatively, also the intensity ratios of the rhodamine B and the phenanthrene monomer emission could be exploited or the sum of the phenanthrene monomer and excimer fluorescence. To the best of our knowledge, this is the first report of ratiometric sensing utilizing such a versatile type of tricolor emissive dyad probe bearing phenanthrene moieties and showing phenanthrene monomer and excimer emission.
- Fürstenwerth, Paul Christian,Resch-Genger, Ute,Srivastava, Priyanka,Witte, Jan Felix
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supporting information
p. 13755 - 13762
(2021/08/16)
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- Fluorescence energy transfer studies in a cross-linked polyurethane network
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A series of cross-linked polyurethane samples, labeled with dyes suitable for fluorescence energy transfer experiments, were prepared (donor, phenanthrene; acceptor, anthracene).Fluorescence decay profiles for these samples were measured as a function of acceptor concentration.These decays obey Foerster nonradiative energy transfer kinetics, with an energy transfer critical distance (R0) of 26.7 Angstroem.Fluorescence intensities, calculated from the decays by integrating the decay profiles, also fit the Perrin model, with a quenching radius (Rs) of 25.6 Angstroem.The fluorescence decay profiles were further examined with a distribution analysis method, which also revealed uniformly distributed donors and acceptors in the polymer matrices. - Keywords: fluorescence quenching; fluorescence decay; phenanthrene; anthracene; polyurethane
- Yang, Jie,Winnik, Mitchell A.
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p. 1823 - 1830
(2007/10/03)
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- Syntheses of unsymmetrically N,N′-bis (substituted)-4,13-diaza-18-crown-6-ether derivatives as a new electron donor-spacer-acceptor triad
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A simple and general synthetic strategy potentially applicable for the preparation of a wide variety of unsymmetrically N,N′-bis(substituted)-4, 13-diaza-18-crown-6-ether derivatives was reported.
- Morimoto, Minoru,Fukui, Keijiro,Kawasaki, Norioki,Iyoda, Tomokazu,Shimidzu, Takeo
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- A Useful Access to 9-Phenanthrylmethyl Derivatives
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Chloromethylation of phenanthrene to give 9-chloromethylphenanthrene and conversions of this compound into other 9-phenanthrylmethyl derivatives in useful yields are described.
- Fernandez, Franco,Gomez, Generosa,Lopez, Carmen,Santos, Ana
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p. 802 - 803
(2007/10/02)
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