基于新型香豆素苯甲酰腙的Zn~(2+)荧光探针研究
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摘要
设计、合成一种光诱导电子转移型香豆素类席夫碱Zn~(2+)荧光探针。以间苯二酚和苯甲酰乙酸乙酯为原料合成4-苯基-7-羟基香豆素,再在乌洛托品与醋酸条件下合成4-苯基7-羟基-8-甲酰基香豆素,最后与苯甲酰肼反应形成目标产物。通过荧光光谱分析实验发现,目标产物在CH_3CN∶H_2O=9∶1(v∶v)中对Zn~(2+)具有较好的选择性和灵敏性,其荧光强度随着Zn~(2+)浓度的增大而逐渐增强,目标产物与Zn~(2+)的络合比为1∶2。
Design and synthesis of a photoinduced electron transfer type coumarin Schiff base Zn~(2+)fluorescent probe.Synthesis of 4-phenyl-7-hydroxycoumarin from resorcinol and ethyl benzoylacetate,and synthesis of 4-phenyl7-hydroxy-8-formyl group under urotropine and acetic acid Coumarin,which is finally reacted with benzoyl hydrazide to form the target product.It was found by fluorescence spectroscopy that the target product has good selectivity and sensitivity to Zn~(2+) in CH_3CN:H_2O=9:1(v:v),and its fluorescence intensity gradually increases with the increase of Zn~(2+) concentration.The complex ratio of product to Zn~(2+) was 1∶2.
Design and synthesis of a photoinduced electron transfer type coumarin Schiff base Zn~(2+)fluorescent probe.Synthesis of 4-phenyl-7-hydroxycoumarin from resorcinol and ethyl benzoylacetate,and synthesis of 4-phenyl7-hydroxy-8-formyl group under urotropine and acetic acid Coumarin,which is finally reacted with benzoyl hydrazide to form the target product.It was found by fluorescence spectroscopy that the target product has good selectivity and sensitivity to Zn~(2+) in CH_3CN:H_2O=9:1(v:v),and its fluorescence intensity gradually increases with the increase of Zn~(2+) concentration.The complex ratio of product to Zn~(2+) was 1∶2.
引文
[1]Li Jun,Zhang Chun-fang,Ming Ze-zhong,et al.CoumarinBased Novel Fluorescent Zinc Ion Probe in Aqueous Solution[J].Tetrahedron,2013,6:4743-4748.
[2]WuGuang-fu,Qi Gao,LiMing-xin,et al.A Ratiometric Probe Based on Coumarin-Quinoline for Highly Selective and Sensitive Detection of Zn2+Ions in Living Cells[J].J.Photoch.Photobio.A.,2018,355:487-495.
[3]李长伟,杨栋,尹兵,等.新型香豆素类Zn2+荧光探针的合成及细胞成像研究[J].有机化学,2016(36):784-789.
[4]Mohammad Z J,Hassan ZB,Hassan M.A Coumarin based Highly Sensitive Fluorescent Chemosensor for Selective Detection of Zinc Ion[J].Spectrochim.Acta.A.,2018,207:16-22.
[5]万攀,张锦华,刘炜,等.香豆素类席夫碱型Zn2+荧光探针的合成与研究[J].化学试剂,2017,39(4):413-415.
[6]Watt N T,Whitehouse I J,Hooper N M.The Role of Zinc in Alzheimer's Disease[J].Int.J.Alzheimers Dis.,2010:1-10.
[7]Song Zhan-ke,Dong Biao,Lei Ge-juan,et al.Novel Selective Fluorescent Probes for Sensing Zn2+Ions based on a Coumarin Schiffbase[J].Tetrahedron Lett.,2013,54(36):4945-4949.
[8]Xu Zhao-chao,Liu Xin,Pan Jie,et al.Coumarin-Derived Transformable Fluorescent Sensor for Zn2+[J].Chem.commun.,2012,48(39):4764-4766.
[9]Yan Mi-hui,Li Tian-rong,Yang Zheng-yin.A Novel Coumarin Schiffbase As a Zn(Ⅱ)Ion Fluorescent Sensor[J].Inorg.Chem.Commun.,2011,14(3):463-465.
[10]Kumar V,Kumar A,Diwan U,et al.A Zn2+-Responsive highly Sensitive Fluorescent Probe and 1D Coordination Polymer based on a Coumarin Platform[J].Dalton.T.,2013,42(36):13078-13083.
[11]An Jun-mei,Yan Mi-hui,Yang Zheng-yin,et al.A turn-on Fluorescent Sensor for Zn(Ⅱ)based on Fluorescein-Coumarin Conjugate[J].Dyes Pigm.,2013,99:1-5.
[12]Jeong Y,Yoon J.Recent Progress on Fluorescent Chemosensors for Metal Ions[J].Inorg.Chim.Acta.,2012,381:2-14.
[13]Veale E B,Gunnlaugsson T.Fluorescent Sensors for Ions Based on Organic Structures[J].Annu.Rep.Prog.Chem.Sect.B.,2010,106:376-406.
[14]刘江,张小琴,韩隽,等.香豆素类荧光探针在检测方面的研究进展[J].浙江化工,2010,41(9):27-31.
[15]Tian Ye,Liang Zhen,Xu Hang,et al.Design,Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry[J].Molecules,2016,21(6):1-15.
[16]KrishnaC,BhargaviMV,Krupadanam GLD,et al.Synthesis ofPyrano Isoxazoline/Isoxazole Annulated Coumarins via Intramolecular Nitrile Oxide Cycloaddition and their Cytotoxicity[J].Russ.J.Gen.Chem.,2017,87(8):1857-1863.
[2]WuGuang-fu,Qi Gao,LiMing-xin,et al.A Ratiometric Probe Based on Coumarin-Quinoline for Highly Selective and Sensitive Detection of Zn2+Ions in Living Cells[J].J.Photoch.Photobio.A.,2018,355:487-495.
[3]李长伟,杨栋,尹兵,等.新型香豆素类Zn2+荧光探针的合成及细胞成像研究[J].有机化学,2016(36):784-789.
[4]Mohammad Z J,Hassan ZB,Hassan M.A Coumarin based Highly Sensitive Fluorescent Chemosensor for Selective Detection of Zinc Ion[J].Spectrochim.Acta.A.,2018,207:16-22.
[5]万攀,张锦华,刘炜,等.香豆素类席夫碱型Zn2+荧光探针的合成与研究[J].化学试剂,2017,39(4):413-415.
[6]Watt N T,Whitehouse I J,Hooper N M.The Role of Zinc in Alzheimer's Disease[J].Int.J.Alzheimers Dis.,2010:1-10.
[7]Song Zhan-ke,Dong Biao,Lei Ge-juan,et al.Novel Selective Fluorescent Probes for Sensing Zn2+Ions based on a Coumarin Schiffbase[J].Tetrahedron Lett.,2013,54(36):4945-4949.
[8]Xu Zhao-chao,Liu Xin,Pan Jie,et al.Coumarin-Derived Transformable Fluorescent Sensor for Zn2+[J].Chem.commun.,2012,48(39):4764-4766.
[9]Yan Mi-hui,Li Tian-rong,Yang Zheng-yin.A Novel Coumarin Schiffbase As a Zn(Ⅱ)Ion Fluorescent Sensor[J].Inorg.Chem.Commun.,2011,14(3):463-465.
[10]Kumar V,Kumar A,Diwan U,et al.A Zn2+-Responsive highly Sensitive Fluorescent Probe and 1D Coordination Polymer based on a Coumarin Platform[J].Dalton.T.,2013,42(36):13078-13083.
[11]An Jun-mei,Yan Mi-hui,Yang Zheng-yin,et al.A turn-on Fluorescent Sensor for Zn(Ⅱ)based on Fluorescein-Coumarin Conjugate[J].Dyes Pigm.,2013,99:1-5.
[12]Jeong Y,Yoon J.Recent Progress on Fluorescent Chemosensors for Metal Ions[J].Inorg.Chim.Acta.,2012,381:2-14.
[13]Veale E B,Gunnlaugsson T.Fluorescent Sensors for Ions Based on Organic Structures[J].Annu.Rep.Prog.Chem.Sect.B.,2010,106:376-406.
[14]刘江,张小琴,韩隽,等.香豆素类荧光探针在检测方面的研究进展[J].浙江化工,2010,41(9):27-31.
[15]Tian Ye,Liang Zhen,Xu Hang,et al.Design,Synthesis and Cytotoxicity of Novel Dihydroartemisinin-Coumarin Hybrids via Click Chemistry[J].Molecules,2016,21(6):1-15.
[16]KrishnaC,BhargaviMV,Krupadanam GLD,et al.Synthesis ofPyrano Isoxazoline/Isoxazole Annulated Coumarins via Intramolecular Nitrile Oxide Cycloaddition and their Cytotoxicity[J].Russ.J.Gen.Chem.,2017,87(8):1857-1863.