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  • General Chemistry  (11)
  • fluorescence  (4)
  • 1
    ISSN: 1573-6881
    Keywords: Heart ; biomembranes ; mitochondria ; ions ; transport ; diffusion ; channels ; swelling ; fluorescamine ; fluorescence
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Physics
    Notes: Abstract This report describes experimental results which show that the fluorescent reagent fluorescamine induces mitochondrial energy-independent swelling when the incubation media contain the chloride salts of the cations Li+, Na+, K+, Rb+, and Cs+. The reaction depends on the concentration of the dye and is inhibited by Mg2+, and its extension is closely related to the amount of the primary amino groups titrated by fluorescamine. Analysis of the labeled inner membrane in polyacrylamide gel shows that the amount of aminofluorescamine complex is lower when mitochondria are in the presence of Mg2+.
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  • 2
    ISSN: 0959-8103
    Keywords: anthracene ; fluorescence ; naphthalene ; non-radiative singlet energy transfer ; polyesters ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Steady state fluorescence has been used to study the efficiency of nonradiative single energy transfer for naphthalene → naphthalene and naphthalene → anthracene for polyesters and their bichromophoric model compounds. Polyesters containing only naphthalene groups were derived from 2,6-naphthalene dicarboxylic acid as the rigid unit, and two series of glycols, HO—(CH2)m—OH and HO—(CH2CH2O)n;—OH, where m=2-6 and n=1-4, as flexible spacers. Bichromophoric model compounds were derived from 2-naphthoic acid and the same glycols. In order to study the transfer for naphthalene → anthracene, a first attempt was made by studying bichromophoric model compounds D—(CH2)m—A, where D and A denote 2-naphthoate (donor) and 9-anthranoate (acceptor) groups, respectively. The fluorescence anisotropy measurements in a solid matrix of glassy poly(methyl methacrylate), for the compounds containing only naphthalene groups, and the simple excitation and emission spectra, for the compounds containing naphthalene and antharacene groups, clearly demonstrate the presence of non-radiative singlet-singlet energy transfer, the efficiency of which depends mainly on n (or n). A theoretical treatment using the rotational isomeric state model of the conformatin of these molecules has also been performed. The combination of the experiments and the theoretical analysis establishes that the Förster radii are 1.2 and 1.4 nm for the naphthalene → naphthalene transfer in the bichromophoric model compounds and polyesters, respectively, and 1.6 ± 0.2 nm for the naphthalene → anthracene transfer in the model compounds studied.
    Additional Material: 16 Ill.
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  • 3
    ISSN: 0887-6266
    Keywords: conformation ; excimer ; fluorescence ; hairpins ; polyester ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Notes: The fluorescence in dilute solution has been measured as a function of solvent viscosity for four bichromophoric models for polyesters with naphthalene in the rigid aromatic unit and diols derived from cyclohexane as the flexible spacer. The spacers are 1,2-cis-cyclohexanediol, 1,2-trans-cyclohexanediol, a 1:2 mixture of 1,3-cis- and 1,3-trans-cyclohexanediols, and a 1:2 mixture of 1,4-cis- and 1,4-trans-cyclohexanediols. The shape of the emission spectra for the molecules in this series is less sensitive to the viscosity of the medium than was the case for an analogous series in which a methylene or oxyethylene spacer replaces the cyclohexanediol spacer. The dependence of the excimer emission on the type of spacer is different also in the series in which the rigid units contain naphthalene or benzene. When the rigid units contain naphthalene, excimer formation is maximal if the spacer contains 1,2-trans-cyclohexanediol, but this spacer produces a molecule with a very small tendency for excimer formation in its polymers with terephthalate. A conformational analysis correctly concludes that the spacer most conducive to excimer formation should be 1,2-trans-cyclohexanediol, but it does not identify the correct order of the remaining three bichromophoric model compounds. The problem may reside in the method for taking into account the finite width of the torsional well associated with each rotational isomer. © 1994 John Wiley & Sons, Inc.
    Additional Material: 10 Ill.
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  • 4
    ISSN: 1434-193X
    Keywords: Co-conformation ; Molecular recognition ; Planar chirality ; Rotaxanes ; Template-directed synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The template-directed syntheses of three [2]rotaxanes possessing either chiral centers or elements of planar chirality, in one of their two mechanically interlocked components, have been realized and their solid-state structures have been analyzed by X-ray crystallography. In one instance, an enantiomerically pure dumbbell-shaped component incorporating a 1,5-dioxynaphthalene recognition site and two (1R,2S,5R)-menthyl stoppers was employed to template the formation of the achiral tetracationic cyclophane, cyclobis(paraquat-p-phenylene). The resulting enantiomerically pure [2]rotaxane was isolated in a yield of 55%. In the other two instances, an achiral 1,5-dioxynaphthalene-based dumbbell-shaped component was employed to template the formation of bipyridinium-based cyclophanes possessing either one or two elements of planar chirality. The resulting [2]rotaxane, possessing one element of planar chirality, was isolated as a racemate in a yield of 24%. The related [2]rotaxane, possessing two elements of planar chirality, was isolated as a mixture of a meso form and an enantiomeric pair in an overall yield of 28%. The 1H-NMR-spectroscopic analysis of this mixture revealed a diastereoisomeric ratio of 4:1. A degenerate co-conformational change was identified by variable-temperature 1H-NMR spectroscopy in all [2]rotaxanes. The symmetry loss arising from the introduction of one or two elements of planar chirality enabled the elucidation of the mechanism of this dynamic process in two instances.
    Additional Material: 12 Ill.
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  • 5
    ISSN: 1434-193X
    Keywords: Catenanes ; Mechanically interlocked molecules ; Molecular recognition ; Rotaxanes ; Template-directed synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A [2]catenane, able to bind π-electron-rich guests inside the cavity of one of its two macrocyclic components has been designed and synthesized using supramolecular assistance. This recognition motif has been exploited to template the formation of a so-called rotacatenane - i.e., a molecule composed of a dumbbell-shaped component threaded through the cavity of one of the two mechanically interlocked macrocyclic components of a [2]catenane. The structure of this [2]catenane, as well as that of a model [2]catenane, have been characterized unequivocally by single-crystal X-ray analyses. Furthermore, some of the co-conformational changes associated with these mechanically interlocked molecules in solution have been probed by variable-temperature 1H-NMR spectroscopy.
    Additional Material: 10 Ill.
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  • 6
    ISSN: 1434-193X
    Keywords: Fluorine ; Cycloadditions ; Nitrones ; Asymmetric induction ; Sulfoxides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 3-(Fluoroalkyl)isoxazolidines 6 and -2,3-dihydroisoxazoles 8 have been obtained in enantiomerically pure form with good diastereoselectivity by 1,3-dipolar cycloaddition of diethyl fumarate and dimethylacetylene dicarboxylate, respectively, to the chiral fluorinated nitrone (R)-5. The latter has been prepared from the β-fluoromethyl-β-oxo sulfoxide (RS)-1, by a synthetic sequence where the chiral and enantiomerically pure sulfinyl function acts as a removable source of chirality. Reductive opening of isoxazolidines 6 then afforded amino fluoromethyl diols 7 in good yields.
    Additional Material: 1 Ill.
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  • 7
    ISSN: 1434-193X
    Keywords: Fluorine ; Lactones ; Annulation ; Ketene ; Sulfoxides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiomerically pure α,α-dichloro β-fluoroalkyl γ-p-tolylthio γ-butyrolactones trans-6a-c have been obtained with excellent stereocontrol (〉 98:2) and enantiomeric purity (〉 98:2) by sulfoxide-directed lactonization (Marino's annu-lation reaction) of β-fluoroalkyl vinyl sulfoxides (R)-(E)-5a-c with dichloroketene. Highly chemoselective dechlorination and desulfurization reactions performed on trans-6c efficiently provided the β-chlorodifluoromethyl γ-butyrolactone (S)-8c, the absolute stereochemistry of which was determined by X-ray diffraction analysis of its γ-p-tolylthio precursor (2R,3S)-7c.
    Additional Material: 1 Ill.
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  • 8
    ISSN: 1434-193X
    Keywords: Fluorine ; Pheromones ; Sulfoxides ; Sulcatol ; Asymmetric synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The pheromone (R)-(-)-sulcatol (10a) and three of its enantiomeric mono-, di-, and trifluoro analogues 10b-d have been synthesized, in six steps and with good overall yields, starting from chiral (R)-2-methyl-5-[(4-methylphenyl)sulfinyl]pent-2-ene (1) and commercially available fluorinated or non-fluorinated acetates.Supporting information for this article is available on the WWW under http://www.wileY-Vch.de/contents/jc_2046/1999/98375_s.pdf or from the author.
    Additional Material: 2 Tab.
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  • 9
    ISSN: 1434-193X
    Keywords: β-Iminosulfoxides ; Quaternary stereocentre ; Pictet-Spengler reaction ; Alkaloids ; Fluorine ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomerically pure 1-trifluoromethyl-tetrahydroisoquinoline alkaloid analogues, in which C-1 is a quaternary stereogenic centre, have been synthesized by stereoselective intramolecular Pictet-Spengler reaction of the N-arylethyl γ-trifluoro-β-iminosulfoxide (R)-3, and subsequent elaborations of the sulfinyl auxiliary. The absolute stereochemistry of the stereogenic centre was determined by X-ray diffraction on the α-phenylpropionic ester (1R,2′S)-10.
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  • 10
    ISSN: 1434-193X
    Keywords: Fluorinated dideoxynucleosides ; Through-space interactions ; Hydrogen bonds ; Long-range coupling constants ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A collection of 5′-O-benzyl-2′,3′-dideoxy-4′-(fluoromethyl)nucleosides carrying both purinic and pyrimidinic nucleobases (uracil, 5-Br-uracil, 5-O2N-uracil, 6-Cl-purine and inosine) were synthesized in both the α and the β form. Through-space-transmitted 6JCF NMR coupling constants between F and C-6 (pyrimidinic base) or C-8 (purinic base) were observed for all of the α anomers of the compounds examined, whilst the corresponding 7JHF coupling constants were resolved only for the 5-substituted uracil derivatives. The absolute values of all the through-space couplings were found to decrease monotonically with increasing solvent polarity (CDCl3, MeOD, [D6]acetone, [D6]DMSO). This trend suggests that the through-space interaction is mediated by an intramolecular (sp3)C-F…H-C(sp2) hydrogen bond. The possibility of any relevant solvent-induced conformational change influencing the F/base mutual spatial relationship in the molecules investigated was ruled out by heteronuclear steady-state 1H{19F}-NOE experiments. A linear correlation was observed between 6JCF and 7JHF coupling constants and the Kamlet-Taft's hydrogen bond basicity parameter β. The crystal structures of the α and β anomers of the 5-nitrouracil nucleoside show evidence that the H-6 of the nucleobase forms hydrogen-bond-like interactions involving the O-benzyl oxygen atom in the β anomer, and that in the case of the α anomer this is replaced by the F atom of the fluoromethyl group.
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