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Relationship between the fluorescence intensities and physico-chemical properties of gallium and aluminium chelates of 2-hydroxyphenylazomethine and 2, 2'-dihydroxyazobenzene derivatives
Abstract
Several 2-hydroxyphenylazomethine and 2, 2'-dihydroxyazobenzene derivatives were prepared and the effect of the physico-chemical properties of substituent groups on the fluorescence intensity of aluminium and gallium chelates were investigated. The utilized regression analysis is the same technique used in Hansch-Fujita's method, an analytical technique known to describe quantitatively the structure-activity relationships (QSAR) of a series of chemical analogs. Using the partition coefficient log P and Hammett constantσ as parametcrs, fairly good correlations were observed for the fluorescence intensities ofthe test compounds. It is suggested that the technique could be applicable to the quantitative analysis of derivatives having the same basic structure as well as structure-biological activity relationships.
... [28][29][30][31][32][33][34][35][36][37][38][39] However, derivatives of 2,2 0dihydroxyazobenzene suggested for sensing of metal ions is still rare. 40 Herein, we present a new colorimetric fluorescent turn-on chemosensor molecule that responds to zinc ion using an azobenzene-containing fluorescent molecule, compound 1 (see Scheme 1). There are several advantages for this new fluorescent Zn 2þ chemosensor molecule. ...
This paper presents a new colorimetric reversible fluorescent turn-on chemosensor molecule for zinc ion based on an azobenzene derivative. The basal fluorescence intensity of the chemosensor molecule is little affected under physiological pH 5–9, whilst the excitation (507nm) and emission (610nm) wavelength of the molecular probe for zinc ion is in the visible range.
Photophysical properties of new azobenzene-containing compounds (E)-2-((2-(undec-10-enoyloxy)phenyl)diazenyl)phenol (1) and 2-((E)-(2-((E)-3-bromoallyloxy)phenyl)diazenyl)phenol (2) were studied at various pH levels. The two substituents, 1 (pKa 9.38) and 2 (pKa 11.38) exhibited large differences in their sensing characteristics toward metal cations. 1 can act as a fluorescent INHIBIT logic gate driven by pH (HO−) and Zn2+ ions, while 2 can be made to operate OR logic gate by appropriate interaction with HO− and Cu2+ as chemical inputs.
A 'novel' and cost-effective 'on-off'-type monophosphate H(2)PO(4)(-) (Pi) chemosensor based on the mononuclear 2,2'-dihydroxyazobenzene (DHAB)-Zn(ii) complex was developed and a molecular keypad lock can be realized in the DHAB-based system by using Zn(ii) cations and Pi anions as inputs.
The preparation and structures of 2, 2′-dihydroxyazobenzenato-dibutyl-tin [Bu2SnL] and 2, 2′-dihydroxyazobenzenato-dimethyl-tin [Me2SnL] are described. The complexes were characterized by IR, NMR (1H, 13C, 119Sn) and UV/VIS spectra. The crystal structures were determined by X-ray diffraction on single crystals. [Bu2SnL]: monoclinic, space group P21/c, cell constants at 208 K: a = 860.73(5), b = 973, 51(18), c = 2340.0(3) pm, β = 93.615(11)°; R1 = 0.0546. [Me2SnL]: orthorhombic, space group Pbcn, cell constants at 208 K: a = 1914.6(4), b = 1041.3(3), c = 1323.27(14) pm; R1 = 0.0529.Organozinn Farbstoffe: Darstellung und strukturelle Charakterisierung von Dibutylzinn- und Dimethylzinn-Komplexen mit 2, 2′-DihydroxyazobenzenDarstellungen und Strukturen von 2, 2′-Dihydroxyazobenzenato-dibutyl-zinn (Bu2SnL) und 2, 2′-Dihydroxyazobenzenato-dimethyl-zinn [Me2SnL] werden beschrieben. Die Komplexe wurden durch IR-, NMR (1H, 13C, 119Sn)- und UV/VIS-Spektren charakterisiert. Die Kristallstrukturen ließen sich durch Röntgenbeugung an Einkristallen bestimmen. [Bu2SnL]: monoklin, Raumgruppe P21/c, Gitterkonstanten bei 208 K: a = 860.73(5), b = 973, 51(18), c = 2340.0(3) pm, β = 93.615(11)°; R1 = 0.0546. [Me2SnL]: orthorhombisch, Raumgruppe Pbcn, Gitterkonstanten bei 208 K: a = 1914.6(4), b = 1041.3(3), c = 1323.27(14) pm; R1 = 0.0529.
A HPLC method using a fluorescence detector is described for the determination of halogenated benz(a)anthracenes (BAX, x=Cl or Br) in water. It consists of the following three procedures; (1) liquid-liquid extraction of BAX with benzene, (2) elimination of interfering compounds from the extracts by one dimensional dual-band thin layer chromatography, and (3) quantitative determination of BAX by HPLC equipped with a fluorescence detector. The recoveries of BAX from water samples through the entire analytical procedure amounted to more than 72%. The calibration curves for BAX were linear, e.g., with a range from 1 to 20 ng ml–1 for 7-chlorobenz(a)anthracene (BACl). The lower detection limit for BACl was 20 pg for an injection volume of 20 l. This method has been applied to BAX in river water spiked with benz(a)anthracene [B(a)A] at 10 ng ml–1 after chlorination. B(a)A, BACl and BABr were found in the levels of 2.01, 0.16 and 0.13 or less ng ml–1, respectively.
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