2598-30-3Relevant articles and documents
Selective fluorescence turn-on of a prefluorescent azomethine with Zn 2+
Knipping, Etienne,Roche, Ivan Ulliel,Dufresne, Stephane,McGregor, Nicholas,Skene
, p. 4385 - 4387 (2011)
A prefluorescent conjugated azomethine (4) was prepared by condensing 8-hydroxyquinoline-5-carbaldehyde with 2-amine thiophene. The fluorescence of the azomethine was quenched in organic solvents including dichloromethane, methanol, DMSO, and DMF. However, the fluorescence of 4 was selectively revived in the presence of zinc and an absolute quantum yield Φfl = 0.15 was measured.
A novel photochemical sensor based on quinoline-functionalized phenazine derivatives for multiple substrate detection
Wei, Tai-Bao,Dong, Hong-Qiang,Ma, Xiao-Qiang,Yang, Qing-Yu,Wang, Zhong-Hui,Guan, Wen-Li,Zhang, Yun-Fei,Zhang, You-Ming,Yao, Hong,Lin, Qi
, p. 5040 - 5048 (2021)
A novel photochemical sensor (FQ-5) based on quinoline-functionalized phenazine derivatives was designed and synthesized. TheFQ-5showed a good response to certain pH values in a wide pH range (from 2.0 to 13.0). Particularly, at pH = 12 and 13, the fluorescence emission showed obvious enhancement, the fluorescence quantum yields could reach 80.9% and 77.0%, respectively, and the color of solution changed from yellow to purple. Meanwhile, the sensor not only showed a rapid response toward CO2, but also showed high selectivity and sensitivity for the detection ofl-Arg in buffer solution (pH = 7), and the limit of detection (LOD) was 8.1 × 10?8. Furthermore, theFQ-5-based fluorescent writing material and CO2gas reaction device were developed for the rapid detection ofl-Arg and CO2. Therefore, this work will provide a new approach for photochemical sensing in the detection of multiple substrates.
8-hydroxyquinoline-substituted boron-dipyrromethene compounds: Synthesis, structure, and OFF-ON-OFF type of pH-sensing properties
Chen, Yuting,Wang, Hailong,Wan, Liang,Bian, Yongzhong,Jiang, Jianzhuang
, p. 3774 - 3781 (2011)
A series of four novel 8-hydroxyquinoline-substituted boron-dipyrromethene derivatives, namely 4,4-difluoro-8-(5-(8-hydroxyquinoline))-3,5-dimethyl-4-bora- 3a,4a-diaza-s-indacene (1), 4,4-difluoro-8-(5-(8-hydroxyquinoline))-1,3,5,7- tetramethyl-4-bora-3a,4a-diaza-s-indacene (2), 4,4-difluoro-8-(5-azastyryl-(8- hydroxyquinoline))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (3), and 4,4-difluoro-8-(5-azastyryl-(8-hydroxyquinoline))-1,3,5,7-tetramethyl-4-bora-3a, 4a-diaza-s-indacene (4), have been synthesized and characterized by a series of spectroscopic methods. The molecular structures of 1 and 2 have been determined by single-crystal X-ray diffraction analyses. The two methyl substituents attached at C-1 and C-7 positions of boron-dipyrromethene (Bodipy) in compound 2 was revealed to prevent the free rotation of the 8-hydroxyquinoline (8-HQ) moiety, resulting in an almost vertical 8-HQ-Bodipy configuration of this compound. This is obviously different from those for 1 with the dihedral angle between 8-hydroxyquinoline and Bodipy moieties of 65.44 and 66.79° due to the lack of methyl substituents in the latter compound. The intense fluorescence from the Bodipy subunit of these compounds was revealed to gradually get diminished along with either decreasing or increasing the pH value under acidic and basic conditions, respectively, in particular for 1, 2, and 4 because of the photoinduced intramolecular electron transfer from excited Bodipy moiety to 8-HQ unit and just an opposite process. This renders these compounds the first OFF-ON-OFF type of pH-dependent fluorescent sensors. Nevertheless, both the intrinsic fluorescence of these compounds and their fluorescent quenching properties along with the change in the pH value have been found to depend on the steric configuration as well as the linking group between 8-hydroxyquinoline and Bodipy moieties, revealing the effect of molecular structure on their fluorescence properties.
Spectral behavior and pH dependence of N-hexadecyl-5-iminomethyl-8-hydroxyquinoline
Jiang, Chaoyang,He, Weijiang,Tai, Zihou,Ouyang, Jianming
, p. 1399 - 1407 (2000)
A new kind of amphiphile derived from 8-hydroxyquinoline, N-hexadecyl-5-iminomethyl-8-hydroxyquinoline (HIHQ) was synthesized and characterized by different physical methods. The influence of pH value on UV-vis absorption, fluorescence spectra were investigated and the surface pressure-area isotherms were recorded under different pH subphase. The linear response range between the emission intensity and the concentration of HIHQ was 1-4×10-6 mol L-1. The strongest emission of HIHQ about 460 nm was obtained at pH 8.2 and the acid-base equilibrium of HIHQ in monolayer and solution was also discussed.
A covalently bonded AlQ3/SiO2 hybrid material with blue light emission by a conventional sol-gel approach
Zeng, Hongyu,Huang, Weimin,Shi, Jianlin
, p. 880 - 881 (2006)
We report the design and synthesis of a covalently bonded AlQ 3/SiO2 hybrid material with strong blue light emission by a sol-gel approach, which make AlQ3 solution-processable and chemically stable. The Royal Society of Chemistry 2006.
A quinoline-based chromogenic and ratiometric fluorescent probe for selective detection of Mg2+ ion: Design, synthesis and its application in salt lake brines and bioimaging
Fu, Zhen-Hai,Peng, Yu,Qin, Jing-Can,Wang, Ya-Wen,Zhang, Yong-Ming,Zhang, Zhi-Hong,Zhao, Dong-Mei
, (2021)
A fluorescent probe was rational designed and prepared to distinguish Mg2+ ion from Ca2+ ion, in which 8-hydroxyquinoline acted as not only a fluorophore but also a recognition group. Notably, this probe QB (8-hydroxyquinoline-5-benzothiazole) shows two fluorescence response modes for highly selective detection of Mg2+ ion, namely fluorescence ratiometric mode and turn-on mode, which can be realized by controlling the excitation wavelength at 356 nm or 425 nm. After the addition of Mg2+ ion, the color of the QB solution changed from colorless to yellow, which can be easily found by naked eye. All experimental results suggested that probe QB has a high selectivity toward Mg2+ ion in the presence of other cations. Its detection limit for Mg2+ ion was estimated as low as 0.142 μM, and this value was far lower than the intracellular concentration (0.5–1.2 mM). The detection mechanism was proposed further by the experiment of 1H NMR titration and theoretical calculation. More significantly, this probe was successfully used to detect Mg2+ ion in brine samples as a quantitative method, and was also applied to detecting and imaging Mg2+ ion in living cells, indicating its great application value in practical use for the detection of Mg2+ ion.
Characterization of N-hexadecyl-5-iminomethyl-8-hydroxyquinoline and oriented crystallization of CuSO4?5H2O under its monolayer
Jiang, Chaoyang,Tang, Ruikang,Tai, Zihou
, p. 81 - 84 (1998)
A new amphiphilic ligand, N-hexadecyl-5-iminomethyl-8-hydroxyquinoline (HIHQ), has been synthesized in a convenient method and the characteristics of its monolayer on pure water and on a subphase containing copper ions investigated. LB films of HIHQ were studied by small angle X-ray scattering, UV-VIS and XPS spectra. An oriented crystallization was examined at the monolayer/water interface. A good selection of the (110) crystal face of CuSO4?SH2O occurred at the solid state of the monolayer due to the perfect match between this crystal face and the definite lattice structure of the monolayer.
Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbaldehydes and their Schiff base derivatives
Wantulok, Jakub,Szala, Marcin,Quinto, Andrea,Nycz, Jacek E.,Giannarelli, Stefania,Sokolová, Romana,Ksi??ek, Maria,Kusz, Joachim
, (2020)
A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.
Design and synthesis of Alq3-functionalized polymers
Meyers, Amy,Weck, Marcus
, p. 1766 - 1768 (2003)
Synthesis of an Alq3-containing monomer and its chain-growth polymerization were demonstrated via ring-opening metathesis polymerization. Polymerization was complete within 12 h under mild polymerization conditions and solubility could be tailored via the incorporation of a comonomer. All copolymers retained the absorption and emission properties of Alq3 in solution. This indicated that the polymer coil did not interfere with the luminescence properties of the pendant Alq3 groups.
Four D-A ’ - (π-A)2 Polyalkylated pyridine derivative alloy metal complex as well as preparation method and application thereof
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Paragraph 0035-0040; 0043, (2021/09/01)
The invention relates to four 1-D A (π-’ -) shown A. 2 The polymeric alkylated pyridine derivative alloy belongs to the complex BDTT-PBD-Cd. The invention BDTT-PBD-Zn, BDTT-PBD-Cu and BDTT-PBD-Ni, and a preparation method and application thereof, wherein the metal complex formed by coordination of alkylated pyridine derivatives as a main ligand and a metal serves as an electron donor BDTT, and D-Heck D (π-A A) is synthesized through ’ - reaction. 2 The photovoltaic performance test based on the dye-sensitized solar cell taking BDTT-PBD-Cd, BDTT-PBD through Zn, BDTT-PBD-Cu and BDTT-one-PBD as the dye sensitizer has a good effect: the thermal decomposition temperature is above Ni 176 °C 7.02% 8.55% 9.76%, the thermal stability is good PCE, and the dye-sensitized 6.51 solar cell has a certain prospect in the aspect of application of the dye-sensitized solar cell.
