Photon harvesting polymers: intracoil energy transfer in anthryl- and fluorescein-tagged polystyrene

Hargreaves, John S.; Webber, S. E.

doi:10.1139/v85-224

Cited by 5 publications

(5 citation statements)

References 8 publications

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“…It is known from the literature, that the reaction of fluorescein with benzyl chloride leads both to the benzylation of the hydroxyl and carboxyl groups of the dye. 64,65 Similarly, the direct benzylation of fluorescein with the use of 4-(iodomethyl)phenylboronic acid pinacol ester results in the dibenzylated derivative of the dye (Scheme S1A), as it has been recently shown for the reaction with 4-(bromomethyl)phenylboronic acid pinacol ester. 37 As a consequence, the synthesized probe is characterized by a reduced sensitivity toward oxidants, as there are two distinct reaction pathways of the oxidative deboronation, and only one leads to the formation of the fluorescent compound (Scheme 1A).…”

Section: ■ Results and Discussionmentioning

confidence: 78%

Characterization of Fluorescein-Based Monoboronate Probe and Its Application to the Detection of Peroxynitrite in Endothelial Cells Treated with Doxorubicin

Dębowska

Dębski

Dybała-Defratyka

et al. 2016

Chem. Res. Toxicol.

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Boronate probes have emerged recently as a versatile tool for the detection of reactive oxygen and nitrogen species. Here, we present the characterization of a fluorescein-based monoboronate probe, a 4-(pinacol boronate)benzyl derivative of fluorescein methyl ester (FBBE), that proved to be useful to detect peroxynitrite in cell culture experiments. The reactivity of FBBE toward peroxynitrite as well hypochlorite, hydrogen peroxide, and tyrosyl hydroperoxide was determined. Second-order rate constants of the reactions of FBBE with peroxynitrite, HOCl, and H2O2 at pH 7.4 were equal to (2.8 ± 0.2) × 10(5) M(-1) s(-1), (8.6 ± 0.5) × 10(3) M(-1) s(-1), and (0.96 ± 0.03) M(-1) s(-1), respectively. The presence of glutathione completely blocked the oxidation of the probe by HOCl and significantly inhibited its oxidation by H2O2 and tyrosyl hydroperoxide but not by peroxynitrite. The oxidative conversion of the probe was also studied in the systems generating singlet oxygen, superoxide radical anion, and nitric oxide in the presence and absence of glutathione. Spectroscopic characterization of FBBE and its oxidation product has been also performed. The differences in the reactivity pattern were supported by DFT quantum mechanical calculations. Finally, the FBBE probe was used to study the oxidative stress in endothelial cells (Ea.hy926) incubated with doxorubicin, a quinone anthracycline antibiotic. In endothelial cells pretreated with doxorubicin, FBBE was oxidized, and this effect was reversed by PEG-SOD and L-NAME but not by catalase.

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Section: ■ Results and Discussionmentioning

confidence: 78%

Characterization of Fluorescein-Based Monoboronate Probe and Its Application to the Detection of Peroxynitrite in Endothelial Cells Treated with Doxorubicin

Dębowska

Dębski

Dybała-Defratyka

et al. 2016

Chem. Res. Toxicol.

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“…For X(DPA)* and fluorescein R0 has been estimated as 41 Á. 28 As was noted in the Results, iprc seems to be diminished by ~25% when polymer bound, and likewise the quantum yield of fluorescence of X(DPA)* is decreased, which affects eq 3 because For a DPA-FTC pair separated by r the quantum yield of energy transfer from eq 2 would be given by x(r) = & ( )/(^ ( ) + &°dpa) = [1 + (r/Ro)6]-1 (5) If we associate our measured with an average r value (r), then r/R0 = (1/xl)1/e (6)…”

Section: Discussionmentioning

confidence: 84%

“…This demonstrates that the energy-transfer process is essentially equivalent to static quenching, similar to what has been observed in our earlier work. 5 The fluorescence lifetime of sensitized fluorescein emission is very similar to protein-bound or free fluorescein. For the methanol solvent the polymer-bound fluorescein lifetime is slightly longer than free fluorescein lifetime in methanol.…”

Section: Resultsmentioning

confidence: 96%

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Water-soluble photon-harvesting polymers: intracoil energy transfer in anthryl- and fluorescein-tagged poly(vinylpyrrolidinone)

Hargreaves¹,

Webber²

1985

Macromolecules

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Poly(vinylpyrro1idinone) containing small mole fractions of pendent 9,lO-diphenylanthracene (DPA) and fluorescein (F) was prepared. These copolymers are soluble in polar solvents such as methanol and water. Absorption of light by DPA results in efficient intracoil sensitization of the '(F)* state. The quantum efficiency (x) of this process was determined to be 0.4 in methanol and 0.8 in water. It is demonstrated that this increase in x corresponds to a decrease in polymer coil size in water. Analysis of the fluorescence decay also demonstrata (1) the intracoil energy-transfer process is essentially a static process and (2) anthryl agg-regation can result in nonexponential fluorescence decay, which is interpreted as a dynamic equilibrium between '(DPA)* and a nonfluorescent dimer state. Fluorescence quenching demonstrates that these polymers are not homogeneous and apparently self-organize into hydrophobic and hydrophilic regions.

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“…Mass spectra were recorded using a Micromass Q-TOF-2TM mass spectrometer and CHCl 3 as the solvent. Fluorescence quantum yields ( Ø F ) were calculated using fluorescein as a reference ( Ø F = 0.55 in DMF) [ 61 ]. Melting points were determined with a Büchi B-540 apparatus.…”

Section: Methodsmentioning

confidence: 99%

A Convenient Synthesis of Diketopyrrolopyrrole Dyes

Almodôvar

Tomé

2021

Molecules

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Diketopyrrolo[3,4-c]pyrroles (DPP) are high-performance organic optoelectronic materials. They have applications in solar cells, fluorescent probes, bioimaging, photodynamic/photothermal therapy, and in many other areas. This article reports a convenient two-step synthesis of various DPP dyes from Pigment Red 254, an inexpensive commercial pigment. The synthesis includes a Suzuki–Miyaura cross-coupling reaction of a bis(4-chlorophenyl)DPP derivative with aryl and hetaryl boronic acids under mild reaction conditions. The new dyes show large Stokes shifts and high fluorescence quantum yields, important features for their potential use in technical and biological applications.

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Photon harvesting polymers: intracoil energy transfer in anthryl- and fluorescein-tagged polystyrene

Cited by 5 publications

References 8 publications

Characterization of Fluorescein-Based Monoboronate Probe and Its Application to the Detection of Peroxynitrite in Endothelial Cells Treated with Doxorubicin

Characterization of Fluorescein-Based Monoboronate Probe and Its Application to the Detection of Peroxynitrite in Endothelial Cells Treated with Doxorubicin

Water-soluble photon-harvesting polymers: intracoil energy transfer in anthryl- and fluorescein-tagged poly(vinylpyrrolidinone)

A Convenient Synthesis of Diketopyrrolopyrrole Dyes

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