苝酰亚胺衍生物荧光探针的制备及对金属离子的识别
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摘要
苝酰亚胺衍生物(perlenediimides derivatives,PDIs)作为一类性能优异的新型光电材料,由于其良好的光电性能和强的化学可修饰性,使其在荧光探针方面有着良好的应用前景。以提高苝酰亚胺衍生物溶解性能、改善选择性能为研究切入点,以四氯苝酐为原料,在主链引入供电子基吡啶-2-甲氨基,制备苝酰亚胺衍生物N,N-二(吡啶-2-甲基)-1,6,7,12-四氯-3,4:9,10-苝二酰亚胺(PTCDI-ABD),并对其与Pb~(2+)、Cu~(2+)、Mg~(2+)、Ni~(2+)、Zn~(2+)、K~+、Na~+等金属离子络合后的荧光性能进行详细研究,确定特征金属离子,准确实现金属离子识别。研究证明该化合物分子结构的优化增加了其在空气中的稳定性,与金属离子络合后(即使在较低浓度0.1×10~(-5) mol·L~(-1)),吸收光谱发生蓝移,随着时间的延长,Cu~(2+)的存在导致荧光淬灭。研究显示该化合物是一个很好的Cu~(2+)荧光探针,准确度高、灵敏度强、选择性好、操作简便,容易进行大规模生产和标准化控制。
Perlenediimides derivatives(PDIs)as a kind of excellent photoelectric material,it had good application prospect in fluorescent probes due to its good optical performance and strong chemical modification.The breakthrough point of the research was to improve the dissolve performance and selectivity of perylenediimide derivatives.Designed and synthesised perylenediimide derivatives N,N-bis(2-methylpyridine)-1,6,7,12-tetrachlo-roperylene-3,4:9,10-tetracarboxyl diimide(PTCDI-ABD)bearing 2-aminomethyl pyridine group on the main chain at tetrachloroperylene tetrahydride,and fluorescence performance was studied after complexated with Pb~(2+)、Cu~(2+)、Mg~(2+)、Ni~(2+)、Zn~(2+)、K~+、Na~+ and other metal ions,determined characteristic metal ions and implementated the identification of metal ions accurately.The studies have shown that optimization optimization of the molecular structure of compounds increased the stability in the air,blue shift occurred in the absorption spectrum after complexated with metal ions(even at low concentration 0.1×10~(-5)mol·L~(-1)),the presence of Cu~(2+) resulted in fluorescence quenching over time.The result lied in that the compound is a very good fluorescence probe of Cu~(2+),high accuracy,strong sensitivity,good selectivity,simple operation,carried out large-scale production and standardized control easily.
Perlenediimides derivatives(PDIs)as a kind of excellent photoelectric material,it had good application prospect in fluorescent probes due to its good optical performance and strong chemical modification.The breakthrough point of the research was to improve the dissolve performance and selectivity of perylenediimide derivatives.Designed and synthesised perylenediimide derivatives N,N-bis(2-methylpyridine)-1,6,7,12-tetrachlo-roperylene-3,4:9,10-tetracarboxyl diimide(PTCDI-ABD)bearing 2-aminomethyl pyridine group on the main chain at tetrachloroperylene tetrahydride,and fluorescence performance was studied after complexated with Pb~(2+)、Cu~(2+)、Mg~(2+)、Ni~(2+)、Zn~(2+)、K~+、Na~+ and other metal ions,determined characteristic metal ions and implementated the identification of metal ions accurately.The studies have shown that optimization optimization of the molecular structure of compounds increased the stability in the air,blue shift occurred in the absorption spectrum after complexated with metal ions(even at low concentration 0.1×10~(-5)mol·L~(-1)),the presence of Cu~(2+) resulted in fluorescence quenching over time.The result lied in that the compound is a very good fluorescence probe of Cu~(2+),high accuracy,strong sensitivity,good selectivity,simple operation,carried out large-scale production and standardized control easily.
引文
[1]冷玲,李壹,熊晓辉.重金属检测荧光传感技术的研究进展[J].食品工业科技,2016,37(15):380-384,389.
[2]Samuel K,Montserrat S,Cristal F G,et al.New insights into mercury bioaccumulation in deep-sea organisms from the NW Mediterranean and their human health implications[J].Sci Total Environ,2013,442(1):329-335.
[3]钟丽娜,杨乐.苝酰亚胺化合物在荧光探针中的应用进展[J].化学工程与装备,2015,7:214-216.
[4]Zhang Z,Lu S,Sha C,et al.A single thiourea-appended 1,8-naphthalimide chemosensor for three heavy metal ions:Fe3+,Pb2+,and Hg2+[J].Sensor Actuat B Chem,2015,208:258-266.
[5]Meng L,Ha obo G,Arrowsmith R L,et al.Ditopic boronic acid and imine-based naphthalimide fluorescence sensors for copper(II)[J].Chem Comm,2014,50(80):11806-11809.
[6]Zhang S S,Wang X J,Huang Y W,et al,Ammonia sensing properties of perylene diimides:Effects of core-substituted chiral groups[J].Sensor Actuat B,2018,254(6):805-810.
[7]Liu X T,Huang Z J,Huang Y W,et al.Tunable supramolecular helical aggregate and optoelectrical properties of perylene diimides by stereoisomerism of sugar[J].J Phys Chem C,2017,121(13):7558-7563.
[8]付丽娜,张翠利,黄永伟.吸电子基对苝酰亚胺衍生物气敏传感性能的影响[J].河南大学学报:自然科学版,2014,44(6):654-658.
[9]Gao Y G,Tang Q,Shi Y D,et al.1,8-Naphthalimide modified[12]aneN3 compounds as selective and sensitive probes for Cu2+ ions and ATP in aqueous solution and living cells[J].Talanta,2016,152:438-446.
[10]Liu X T,Zhai H Y,Zhang S S,et al.Impact of alkyl chain and bay-phenoxy unit on the sensing performance of perylenediimide derivatives[J].Sensor Actuat B,2017,243(11):500-506.
[11]Han A X,Glenn D Prestwich,Zang L,et al.Fluorescent sensor for Hg2+ detection in aqueous solution[J].Sensor Actuat B,2014,198(198):274-277.
[12]翟荣佳,刘娅静,赵鑫,等.一种罗丹明类Cu2+荧光探针化合物的合成及性能研究[J].化学研究与应用,2018,27(9):1277-1282.
[13]马永山,孙友敏,吴俊森,等.水溶性苝系衍生物荧光探针的合成及对金属离子的识别[J].分析测试技术与仪器,2011,17(1):47-50.
[14]Yue P,Zhang Y,Guo Z F,et al.Synthesis of bifunctional molecules containing[12]aneN3 and coumarin moieties as effective DNA condensation agents and new non-viral gene vectors[J].Org Biomol Chem,2015,13(15):4494-4505.
[15]Wang Y F,Zhang L,Zhang G J,et al.A new colorimetric and fluorescent bifunctional probe for Cu2+and F-1 ions based on perylene bisimide derivatives[J].Tetrahedron Lett,2014,55(21):3218-3222.
[16]袁石状,张征宇,王恩举.基于萘酰亚胺的Hg2+和Cu2+荧光探针[J].化学研究与应用,2018,30(3):339-343.
[2]Samuel K,Montserrat S,Cristal F G,et al.New insights into mercury bioaccumulation in deep-sea organisms from the NW Mediterranean and their human health implications[J].Sci Total Environ,2013,442(1):329-335.
[3]钟丽娜,杨乐.苝酰亚胺化合物在荧光探针中的应用进展[J].化学工程与装备,2015,7:214-216.
[4]Zhang Z,Lu S,Sha C,et al.A single thiourea-appended 1,8-naphthalimide chemosensor for three heavy metal ions:Fe3+,Pb2+,and Hg2+[J].Sensor Actuat B Chem,2015,208:258-266.
[5]Meng L,Ha obo G,Arrowsmith R L,et al.Ditopic boronic acid and imine-based naphthalimide fluorescence sensors for copper(II)[J].Chem Comm,2014,50(80):11806-11809.
[6]Zhang S S,Wang X J,Huang Y W,et al,Ammonia sensing properties of perylene diimides:Effects of core-substituted chiral groups[J].Sensor Actuat B,2018,254(6):805-810.
[7]Liu X T,Huang Z J,Huang Y W,et al.Tunable supramolecular helical aggregate and optoelectrical properties of perylene diimides by stereoisomerism of sugar[J].J Phys Chem C,2017,121(13):7558-7563.
[8]付丽娜,张翠利,黄永伟.吸电子基对苝酰亚胺衍生物气敏传感性能的影响[J].河南大学学报:自然科学版,2014,44(6):654-658.
[9]Gao Y G,Tang Q,Shi Y D,et al.1,8-Naphthalimide modified[12]aneN3 compounds as selective and sensitive probes for Cu2+ ions and ATP in aqueous solution and living cells[J].Talanta,2016,152:438-446.
[10]Liu X T,Zhai H Y,Zhang S S,et al.Impact of alkyl chain and bay-phenoxy unit on the sensing performance of perylenediimide derivatives[J].Sensor Actuat B,2017,243(11):500-506.
[11]Han A X,Glenn D Prestwich,Zang L,et al.Fluorescent sensor for Hg2+ detection in aqueous solution[J].Sensor Actuat B,2014,198(198):274-277.
[12]翟荣佳,刘娅静,赵鑫,等.一种罗丹明类Cu2+荧光探针化合物的合成及性能研究[J].化学研究与应用,2018,27(9):1277-1282.
[13]马永山,孙友敏,吴俊森,等.水溶性苝系衍生物荧光探针的合成及对金属离子的识别[J].分析测试技术与仪器,2011,17(1):47-50.
[14]Yue P,Zhang Y,Guo Z F,et al.Synthesis of bifunctional molecules containing[12]aneN3 and coumarin moieties as effective DNA condensation agents and new non-viral gene vectors[J].Org Biomol Chem,2015,13(15):4494-4505.
[15]Wang Y F,Zhang L,Zhang G J,et al.A new colorimetric and fluorescent bifunctional probe for Cu2+and F-1 ions based on perylene bisimide derivatives[J].Tetrahedron Lett,2014,55(21):3218-3222.
[16]袁石状,张征宇,王恩举.基于萘酰亚胺的Hg2+和Cu2+荧光探针[J].化学研究与应用,2018,30(3):339-343.