浏览全部资源
扫码关注微信
安庆师范大学 化学化工学院, 功能配合物安徽省重点实验室, 安徽 安庆 246011
[ "徐衡(1968-),女,安徽安庆人,硕士,教授,硕士生导师,2002年于安徽师范大学获得硕士学位,主要从事功能材料的设计及应用方面的研究。E‐mail: xuheng312@163.com " ]
[ "黄荣谊(1975-),男,安徽肥西人,硕士,教授,硕士生导师,2008年于安徽师范大学获得硕士学位,主要从事功能材料的设计及应用方面的研究。E‐mail: huangry@aqnu.edu.cn " ]
纸质出版日期:2022-10-05,
收稿日期:2022-04-19,
修回日期:2022-05-05,
扫 描 看 全 文
徐衡,杨萍,桂乃成等.基于喹啉基的噁二唑酮类荧光探针合成及对Fe3+的识别[J].发光学报,2022,43(10):1636-164410.37188/CJL.20220145.
XU Heng,YANG Ping,GUI Nai-cheng,et al.Synthesis of Oxadiazolidone Fluorescent Probes Based on Quinoline Group and Recognition of Fe3+ Ions[J].Chinese Journal of Luminescence,2022,43(10):1636-164410.37188/CJL.20220145.
徐衡,杨萍,桂乃成等.基于喹啉基的噁二唑酮类荧光探针合成及对Fe3+的识别[J].发光学报,2022,43(10):1636-164410.37188/CJL.20220145. DOI:
XU Heng,YANG Ping,GUI Nai-cheng,et al.Synthesis of Oxadiazolidone Fluorescent Probes Based on Quinoline Group and Recognition of Fe3+ Ions[J].Chinese Journal of Luminescence,2022,43(10):1636-164410.37188/CJL.20220145. DOI:
以8⁃氨基喹啉为原料通过重氮化、还原、酰化等反应制备了3种新的喹啉基酰肼化合物
1~3
,并以其为原料与三光气发生环合反应进一步制备了3种噁二唑酮类化合物
4~6
。6种新的化合物结构均采用红外光谱、核磁共振谱和质谱等技术以及理论计算进行了深入分析。同时通过热重和荧光光谱等手段对化合物的热学和光学性质进行了测试和分析。结果表明,合成的6种化合物都具有良好的热稳定性,且具有较强的固体荧光发射性能。其中,化合物
4~6
可作为荧光探针对Fe
3+
离子具有高选择性和灵敏性的检测能力,其检出限分别为8.70×10
-6
,1.64×10
-6
,1.01×10
-6
mol/L。此外,通过理论计算对6种化合物的发光原理也进行了深入分析。
Three quinolinyl hydrazines
1-3
were prepared from 8-aminoquinoline by diazotization, reduction and acylation reactions, and three oxadiazoles fluorescent probes
4-6
for Fe
3+
were prepared by cyclization reaction with triphosgene. The structures of the six new compounds were characterized by IR, NMR and MS. At the same time, the thermal and optical properties of these compounds were tested and analyzed by thermogravimetry and fluorescence. The results show that the six compounds have good thermal stability below 190
o
C, and have strong solid fluorescence emission properties. Among them, the compounds
4-6
can be used as fluorescent probes to detect Fe
3+
and are not disturbed by other common metal ions. The detection limits of these probes are 8.70×10
-6
,1.64×10
-6
,1.01×10
-6
mol/L, respectively. Moreover, the theoretical luminescence principle of compounds is analyzed by density functional theory(DFT) calculation.
8-氨基喹啉噁二唑酮荧光探针铁离子密度泛函理论方法
8-aminoquinolineoxadiazolidonefluorescent probeFe3+ iondensity functional theory(DFT)
GUPTA A, KUMAR N. A review of mechanisms for fluorescent “turn-on” probes to detect Al3+ ions [J]. RSC Adv., 2016, 6(108): 106413-106434. doi: 10.1039/c6ra23682khttp://dx.doi.org/10.1039/c6ra23682k
LV R, WANG J Y, ZHANG Y P, et al. An amino-decorated dual-functional metal⁃organic framework for highly selective sensing of Cr(Ⅲ) and Cr(Ⅵ) ions and detection of nitroaromatic explosives [J]. J. Mater. Chem. A, 2016, 4(40): 15494-15500. doi: 10.1039/c6ta05965ahttp://dx.doi.org/10.1039/c6ta05965a
ROTHE C, CHIANG C J, JANKUS V, et al. Ionic iridium (Ⅲ) complexes with bulky side groups for use in light emitting cells: reduction of concentration quenching [J]. Adv. Funct. Mater., 2009, 19(13): 2038-2044. doi: 10.1002/adfm.200801767http://dx.doi.org/10.1002/adfm.200801767
ROHINI G, RAMAIAH K, SREEKANTH A. Naphthalene dianhydride based selective detection targetable fluorescent probe for monitoring exogenous iron in living cells [J]. Tetrahedron Lett., 2018, 59(43): 3858-3862. doi: 10.1016/j.tetlet.2018.09.028http://dx.doi.org/10.1016/j.tetlet.2018.09.028
刘丽, 胡润泽, 徐陈, 等. 镧系Eu3+配合物修饰的分子印迹聚合物荧光探针制备及其对血红蛋白的传感检测 [J]. 发光学报, 2022, 43(6): 944-951. doi: 10.37188/cjl.20220095http://dx.doi.org/10.37188/cjl.20220095
LIU L, HU R Z, XU C, et al. Preparation of molecularly imprinted polymer fluorescence probe modified by lanthanide Eu3+ complex and hemoglobin sensing detection [J]. Chin. J. Lumin., 2022, 43(6): 944-951. (in English). doi: 10.37188/cjl.20220095http://dx.doi.org/10.37188/cjl.20220095
ELSUCCARY S A A, SALEM A A. Novel flow injection analysis methods for the determination of total iron in blood serum and water [J]. Talanta, 2015, 131: 108-115. doi: 10.1016/j.talanta.2014.07.068http://dx.doi.org/10.1016/j.talanta.2014.07.068
PANTOPOULOS K, PORWAL S K, TARTAKOFF A, et al. Mechanisms of mammalian iron homeostasis [J]. Biochemistry, 2012, 51(29): 5705-5724. doi: 10.1021/bi300752rhttp://dx.doi.org/10.1021/bi300752r
ROUAULT T A. The role of iron regulatory proteins in mammalian iron homeostasis and disease [J]. Nat. Chem. Biol., 2006, 2(8): 406-414. doi: 10.1038/nchembio807http://dx.doi.org/10.1038/nchembio807
BOGALE R F, CHEN Y Z, YE J W, et al. Highly selective and sensitive detection of 4-nitrophenol and Fe3+ ion based on a luminescent layered terbium(Ⅲ) coordination polymer [J]. Sens. Actuators B: Chem., 2017, 245: 171-178. doi: 10.1016/j.snb.2017.01.177http://dx.doi.org/10.1016/j.snb.2017.01.177
VERMA C, TAPADIA K, SONI A B. Determination of iron(Ⅲ) in food, biological and environmental samples [J]. Food Chem., 2017, 221: 1415-1420. doi: 10.1016/j.foodchem.2016.11.011http://dx.doi.org/10.1016/j.foodchem.2016.11.011
SCHNEIDER S A, BHATIA K P. Three faces of the same gene: FA2H links neurodegeneration with brain iron accumulation, leukodystrophies, and hereditary spastic paraplegias [J]. Ann. Neurol., 2010, 68(5): 575-577. doi: 10.1002/ana.22211http://dx.doi.org/10.1002/ana.22211
GHOSH A, MANDAL S, DAS S, et al. Insights into the phenomenon of acquisition and accumulation of Fe3+ in Hygrophila spinosa through fluorimetry and fluorescence images [J]. Tetrahedron Lett., 2020, 61(9): 151520-1-6. doi: 10.1016/j.tetlet.2019.151520http://dx.doi.org/10.1016/j.tetlet.2019.151520
KRATZER J, BOUŠEK J, STURGEON R E, et al. Determination of bismuth by dielectric barrier discharge atomic absorption spectrometry coupled with hydride generation: method optimization and evaluation of analytical performance [J]. Anal. Chem., 2014, 86(19): 9620-9625. doi: 10.1021/ac502093yhttp://dx.doi.org/10.1021/ac502093y
BAŞOĞLU A, TOSUN G, OCAK M, et al. Simple time-saving method for iron determination based on fluorescence quenching of an azaflavanon-3-ol compound [J]. J. Agric. Food Chem., 2015, 63(10): 2654-2659. doi: 10.1021/jf505336dhttp://dx.doi.org/10.1021/jf505336d
郑德论, 张锐龙, 张彩云, 等. 石墨烯复合功能材料及其在重金属离子检测的电化学研究与应用 [J]. 化学世界, 2020, 61(1): 16-32. doi: 10.19500/j.cnki.0367-6358.20180813http://dx.doi.org/10.19500/j.cnki.0367-6358.20180813
ZHENG D L, ZHANG R L, ZHANG C Y, et al. Research and application of graphene functional materials composite and their electrochemical in heavy metal ion detection [J]. Chem. World, 2020, 61(1): 16-32. (in Chinese). doi: 10.19500/j.cnki.0367-6358.20180813http://dx.doi.org/10.19500/j.cnki.0367-6358.20180813
SHERVEDANI R K, HATEFI-MEHRJARDI A, ASADI-FARSANI A. Sensitive determination of iron(Ⅲ) by gold electrode modified with 2-mercaptosuccinic acid self-assembled monolayer [J]. Anal. Chim. Acta, 2007, 601(2): 164-171. doi: 10.1016/j.aca.2007.08.037http://dx.doi.org/10.1016/j.aca.2007.08.037
SONG Y Q, MA Z Y, FANG H C, et al. Au sputtered paper chromatography tandem Raman platform for sensitive detection of heavy metal ions [J]. ACS Sens., 2020, 5(5): 1455-1464. doi: 10.1021/acssensors.0c00395http://dx.doi.org/10.1021/acssensors.0c00395
贾慧劼, 韩利民, 竺宁, 等. 乙酰基二茂铁苯并噻唑探针对Al3+, Cr3+, Fe3+识别性能的研究 [J]. 有机化学, 2019, 39(6): 1753-1760. doi: 10.6023/cjoc201811024http://dx.doi.org/10.6023/cjoc201811024
JIA H J, HAN L M, ZHU N, et al. A study on recognition property of acetylferrocenyl benzothiazole to Al3+, Cr3+ and Fe3+ [J]. Chin. J. Org. Chem., 2019, 39(6): 1753-1760. (in Chinese). doi: 10.6023/cjoc201811024http://dx.doi.org/10.6023/cjoc201811024
GAO J, HE Y Q, CHEN Y C, et al. Reversible FRET fluorescent probe for ratiometric tracking of endogenous Fe3+ in ferroptosis [J]. Inorg. Chem., 2020, 59(15): 10920-10927. doi: 10.1021/acs.inorgchem.0c01412http://dx.doi.org/10.1021/acs.inorgchem.0c01412
ZHU C C, WANG M J, QIU L, et al. A mitochondria-targeting fluorescent Fe3+ probe and its application in labile Fe3+ monitoring via imaging and flow cytometry [J]. Dyes Pigm., 2018, 157: 328-333. doi: 10.1016/j.dyepig.2018.05.008http://dx.doi.org/10.1016/j.dyepig.2018.05.008
LU H F, XU L C, WANG H, et al. 7, 11-diphenyl-8H-acenaphth[1, 2-f] isoindole-8, 10 (9H)-Dione functionalized polysiloxane with aggregation-induced emission: synthesis and highly sensitive detection for Fe3+ [J]. Dyes Pigm., 2021, 193: 109463. doi: 10.1016/j.dyepig.2021.109463http://dx.doi.org/10.1016/j.dyepig.2021.109463
LI B, GU X, WANG M H, et al. A novel “off-on-off” fluorescent probe for sensing of Fe3+ and F- successively in aqueous solution and its application in cells [J]. Dyes Pigm., 2021, 194: 109637. doi: 10.1016/j.dyepig.2021.109637http://dx.doi.org/10.1016/j.dyepig.2021.109637
WANG X, XIONG H, CHEN T H, et al. A phosphorus-doped g-C3N4 nanosheets as an efficient and sensitive fluorescent probe for Fe3+ detection [J]. Opt. Mater., 2021, 119: 111393-1-8. doi: 10.1016/j.optmat.2021.111393http://dx.doi.org/10.1016/j.optmat.2021.111393
WANG G Q, LIU X Q, CAI S K, et al. A pyrene fluorescent probe for rapid detection of ferric ions [J]. J. Fluoresc., 2021, 31(3): 713-718. doi: 10.1007/s10895-021-02695-3http://dx.doi.org/10.1007/s10895-021-02695-3
HOU L J, LIU T, GONG Y L, et al. A turn-on Schiff base fluorescent probe for the exogenous and endogenous Fe3+ ion sensing and bioimaging of living cells [J]. New J. Chem., 2020, 44(45): 19642-19649. doi: 10.1039/d0nj04315jhttp://dx.doi.org/10.1039/d0nj04315j
CAO X R, ZHANG F F, BAI Y J, et al. A highly selective “turn-on” fluorescent probe for detection of Fe3+ in cells [J]. J. Fluoresc., 2019, 29(2): 425-434. doi: 10.1007/s10895-019-02351-xhttp://dx.doi.org/10.1007/s10895-019-02351-x
BRUEL A, LOGÉ C, DE TAUZIA M L, et al. Synthesis and biological evaluation of new 5-benzylated 4-oxo-3, 4-dihydro-5H-pyridazino[4, 5-b] indoles as PI3Kα inhibitors [J]. Eur. J. Med. Chem., 2012, 57: 225-233. doi: 10.1016/j.ejmech.2012.09.001http://dx.doi.org/10.1016/j.ejmech.2012.09.001
徐衡, 熊志, 朱昌海, 等. 8-氨基喹啉席夫碱锌配合物的合成, 晶体结构及发光性质 [J]. 人工晶体学报, 2018, 47(2): 286-291. doi: 10.3969/j.issn.1000-985X.2018.02.009http://dx.doi.org/10.3969/j.issn.1000-985X.2018.02.009
XU H, XIONG Z, ZHU C H, et al. Synthesis, crystal Structure and luminescence property of a zinc complex containing 8-aminoquinoline Schiff base ligand [J]. J. Synth. Cryst., 2018, 47(2): 286-291. (in Chinese). doi: 10.3969/j.issn.1000-985X.2018.02.009http://dx.doi.org/10.3969/j.issn.1000-985X.2018.02.009
高勇, 汪军, 付妹, 等. 水溶性罗丹明基Fe3+荧光探针及其在细胞成像中的应用 [J]. 有机化学, 2017, 37(3): 617-623. doi: 10.6023/cjoc201610014http://dx.doi.org/10.6023/cjoc201610014
GAO Y, WANG J, FU M, et al. A water-soluble rhodamine-based fluorescent probe for Fe3+ and its application in live cell imaging [J]. Chin. J. Org. Chem., 2017, 37(3): 617-623. (in Chinese). doi: 10.6023/cjoc201610014http://dx.doi.org/10.6023/cjoc201610014
ZHANG Z X, LI F, HE C Y, et al. Novel Fe3+ fluorescence probe based on the charge-transfer(CT) molecules [J]. Sens. Actuators B: Chem., 2018, 255: 1878-1883. doi: 10.1212/wnl.52.9.1891http://dx.doi.org/10.1212/wnl.52.9.1891
0
浏览量
202
下载量
0
CSCD
关联资源
相关文章
相关作者
相关机构