1，8-萘酰亚胺衍生物的合成及其在能量转移和pH荧光探针中的应用
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摘要
合成了一系列萘酰亚胺衍生物:N-丁基-4-(2′-氨基乙基)氨基-1,8-萘酰亚胺(EBNT)、N-丁基-4-(6′-氨基己基)氨基-1,8-萘酰亚胺(HBNT)、含有4个1,8-萘酰亚胺荧光团的TEBNT和THBNT。通过红外光谱、核磁共振、质谱、元素分析表征了其结构。改进和优化了这些产物的合成方法,提高了产物的收率。
研究了EBNT、HBNT、TEBNT和THBNT的光物理性能及其与曙红之间的能量转移。固定曙红浓度为2.5*10~(-5) mol·L~(-1),EBNT、HBNT、TEBNT和THBNT与曙红之间的能量转移使得此浓度曙红溶液的荧光部分猝灭,将其按照对曙红的荧光猝灭作用从小到大排列的顺序为:THBNT>HBNT>TEBNT>EBNT。固定EBNT、HBNT、TEBNT和THBNT浓度,能量转移效率随着曙红浓度的增加逐渐增大,在曙红浓度较高时,能量转移效率达90%以上,曙红荧光得到增强。可见EBNT、HBNT、TEBNT和THBNT可以在曙红浓度较高时增强曙红的荧光强度,抵消其自猝灭现象。将其按照对曙红的荧光增强作用从大到小排列的顺序为:HBNT >TEBNT>THBNT>EBNT。
研究了EBNT、HBNT、TEBNT和THBNT在pH探针中的应用。在pH值1.82~12.36范围内,EBNT、HBNT、TEBNT和THBNT的荧光强度受pH值影响较大。EBNT和HBNT的荧光强度随溶液的pH值增大逐渐降低,荧光强度分别在pH8.71~10.50和pH6.51~10.81范围内与pH值呈线性关系,可以作为相应pH值区间的荧光探针。TEBNT和THBNT的荧光强度随pH值的增大先增大后减小,荧光强度分别在pH5.13~5.48和pH8.80~9.15发生突变,增强2倍以上,可以作为相应pH值区间的荧光开关。
Four 1,8-naphthalimide derivatives named N-butyl-4-(2′-amino ethyl)amino-1,8- naphthaimide (EBNT), N-butyl-4(-6′-aminohexyl)amino-1,8-naphthaimide (HBNT), THBNT and TEBNT containing four 1,8-naphthalimide fluorophores were synthesized. Their structures were characterized by FTIR, 1 H-NMR, MS and elementary analysis. The synthesis methods were modified and optimized and high yields were achieved.
Photophysical characteristics of EBNT, HBNT, TEBNT and THBNT and their energy transfer with eosin were investigated: When the concentration of eosin was 2.5*10~(-5) mol·L~(-1), energy transfer between EBNT, HBNT, TEBNT and THBNT resulted in partial fluorescence quenching of eosin. The order of the contribution to quenching from low to high was THBNT>HBNT>TEBNT>EBNT. When the concentration of EBNT, HBNT, TEBNT and THBNT was fixed, the energy transfer efficiency rose with the concentration of eosin increased, and exceeded 90% at high concentration of eosin. HBNT, HBNT, TEBNT and THBNT could enhanced fluorescent intensity of eosin and offset it self-quenching at high concentration. The order of the contribution to enhancement from high to low was HBNT >TEBNT> THBNT>EBNT.
The application of EBNT, HBNT, TEBNT and THBNT in pH fluorescence probes were studied: Between pH 1.82 and 12.36, their fluorescent intensity was greatly affected by pH values. The fluorescent intensity of EBNT and HBNT reduced with the increment of pH values. The fact that the fluorescent intensity of EBNT and HBNT changed linearly from pH8.71 to pH10.50 and pH6.51 to pH10.81 respectively indicated that EBNT and HBNT could be used as pH fluorescence probes. The fluorescent intensity of TEBNT and THBNT first increased with the increment of pH values and then decreased. Their fluorescent intensity increased abruptly from pH5.13 to pH5.48 and pH8.80 to pH9.15 respectively, and almost doubled. The mini-regions of the fluorescence mutation of TEBNT and THBNT reflected that they could be used as pH fluorescent switches.
研究了EBNT、HBNT、TEBNT和THBNT的光物理性能及其与曙红之间的能量转移。固定曙红浓度为2.5*10~(-5) mol·L~(-1),EBNT、HBNT、TEBNT和THBNT与曙红之间的能量转移使得此浓度曙红溶液的荧光部分猝灭,将其按照对曙红的荧光猝灭作用从小到大排列的顺序为:THBNT>HBNT>TEBNT>EBNT。固定EBNT、HBNT、TEBNT和THBNT浓度,能量转移效率随着曙红浓度的增加逐渐增大,在曙红浓度较高时,能量转移效率达90%以上,曙红荧光得到增强。可见EBNT、HBNT、TEBNT和THBNT可以在曙红浓度较高时增强曙红的荧光强度,抵消其自猝灭现象。将其按照对曙红的荧光增强作用从大到小排列的顺序为:HBNT >TEBNT>THBNT>EBNT。
研究了EBNT、HBNT、TEBNT和THBNT在pH探针中的应用。在pH值1.82~12.36范围内,EBNT、HBNT、TEBNT和THBNT的荧光强度受pH值影响较大。EBNT和HBNT的荧光强度随溶液的pH值增大逐渐降低,荧光强度分别在pH8.71~10.50和pH6.51~10.81范围内与pH值呈线性关系,可以作为相应pH值区间的荧光探针。TEBNT和THBNT的荧光强度随pH值的增大先增大后减小,荧光强度分别在pH5.13~5.48和pH8.80~9.15发生突变,增强2倍以上,可以作为相应pH值区间的荧光开关。
Four 1,8-naphthalimide derivatives named N-butyl-4-(2′-amino ethyl)amino-1,8- naphthaimide (EBNT), N-butyl-4(-6′-aminohexyl)amino-1,8-naphthaimide (HBNT), THBNT and TEBNT containing four 1,8-naphthalimide fluorophores were synthesized. Their structures were characterized by FTIR, 1 H-NMR, MS and elementary analysis. The synthesis methods were modified and optimized and high yields were achieved.
Photophysical characteristics of EBNT, HBNT, TEBNT and THBNT and their energy transfer with eosin were investigated: When the concentration of eosin was 2.5*10~(-5) mol·L~(-1), energy transfer between EBNT, HBNT, TEBNT and THBNT resulted in partial fluorescence quenching of eosin. The order of the contribution to quenching from low to high was THBNT>HBNT>TEBNT>EBNT. When the concentration of EBNT, HBNT, TEBNT and THBNT was fixed, the energy transfer efficiency rose with the concentration of eosin increased, and exceeded 90% at high concentration of eosin. HBNT, HBNT, TEBNT and THBNT could enhanced fluorescent intensity of eosin and offset it self-quenching at high concentration. The order of the contribution to enhancement from high to low was HBNT >TEBNT> THBNT>EBNT.
The application of EBNT, HBNT, TEBNT and THBNT in pH fluorescence probes were studied: Between pH 1.82 and 12.36, their fluorescent intensity was greatly affected by pH values. The fluorescent intensity of EBNT and HBNT reduced with the increment of pH values. The fact that the fluorescent intensity of EBNT and HBNT changed linearly from pH8.71 to pH10.50 and pH6.51 to pH10.81 respectively indicated that EBNT and HBNT could be used as pH fluorescence probes. The fluorescent intensity of TEBNT and THBNT first increased with the increment of pH values and then decreased. Their fluorescent intensity increased abruptly from pH5.13 to pH5.48 and pH8.80 to pH9.15 respectively, and almost doubled. The mini-regions of the fluorescence mutation of TEBNT and THBNT reflected that they could be used as pH fluorescent switches.
引文
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