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嘌呤骨架对嘌呤-羟基喹啉并双杂环化合物荧光性质的影响。

Purine scaffold effect on fluorescence properties of purine-hydroxyquinolinone bisheterocycles.

机构信息

Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, Palacký University, Olomouc, Czech Republic.

出版信息

J Fluoresc. 2011 Nov;21(6):2207-12. doi: 10.1007/s10895-011-0925-0. Epub 2011 Aug 9.

DOI:10.1007/s10895-011-0925-0
PMID:21826428
Abstract

The fluorescence properties of bisheterocyclic compounds that contain purine and the 3-hydroxyquinolin-4(1H)-one skeleton connected with an aliphatic spacer of a different length/structure (3HQP) were examined. It was found that the introducing of the spacer-purine scaffold led in the comparison to 3HQs themselves to (1) the possibility of the effectual excitation in the wider range of excitation wavelengths, moreover, some derivatives can be excited at relatively high wavelengths around 400 nm, (2) the lowering of the quantum yield and (3) the slight longer wavelength shift of the dual emission spectra. Tested organic solvents did not affect significantly the 3HQP fluorescence properties. The characters of emission spectra as well as the quantum yields of 3HQPs were notably influenced by the ratio of water and DMSO in their composed mixture applied as a solvent. With increasing water content in the mixture both I(1)/I(2) and the quantum yield decreased.

摘要

研究了含有嘌呤和 3-羟基喹啉-4(1H)-酮骨架的双杂环化合物的荧光性质,该骨架通过不同长度/结构的脂肪间隔基连接。研究发现,与 3HQ 相比,间隔基-嘌呤支架的引入导致:(1) 在更宽的激发波长范围内进行有效激发的可能性,此外,一些衍生物可以在相对较高的 400nm 左右的波长处被激发;(2) 量子产率降低;(3) 双发射光谱的波长略有红移。测试的有机溶剂对 3HQP 的荧光性质没有显著影响。作为溶剂,水和 DMSO 混合比显著影响 3HQP 的发射光谱特性和量子产率。随着混合物中含水量的增加,I(1)/I(2)和量子产率均降低。

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本文引用的文献

1
Solid-phase synthesis of highly diverse purine-hydroxyquinolinone bisheterocycles.高度多样化嘌呤-羟基喹啉酮双杂环的固相合成
J Comb Chem. 2010 Nov 8;12(6):890-4. doi: 10.1021/cc100132z. Epub 2010 Sep 17.
2
Dual-fluorescence probe of environment basicity (hydrogen bond accepting ability) displaying no sensitivity to polarity.对环境碱度(氢键接受能力)具有双重荧光响应的探针,对极性不敏感。
J Fluoresc. 2009 May;19(3):545-53. doi: 10.1007/s10895-008-0443-x. Epub 2008 Nov 20.
3
Steric control of the excited-state intramolecular proton transfer in 3-hydroxyquinolones: steady-state and time-resolved fluorescence study.
3-羟基喹诺酮类化合物激发态分子内质子转移的空间控制:稳态和时间分辨荧光研究
J Phys Chem A. 2007 Sep 20;111(37):8986-92. doi: 10.1021/jp071075t. Epub 2007 Aug 24.