基于ICT萘酰亚胺阳离子比率荧光探针的研究
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摘要
荧光分子探针能够将分子识别的信息转换成荧光信号为外界所感知,具有诸如最高可达单分子检测的高灵敏度、能够实现开关操作、对亚微粒具有可视的亚纳米空间分辨能力和亚毫秒时间分辨能力、原位检测(荧光成像技术)以及利用光纤进行远距离检测等众多优点。比率荧光信号优于荧光强度响应信号,提高了灵敏度,引入自动校准功能,可实现定量检测。所谓比率检测就是指两个荧光发射强度或吸收强度的比值随着底物浓度的变化而变化。比率检测一个突出优点就是通过强度比值的变化提高动态响应的范围,建立起内标从而极大的削弱其他因素的干扰。
4-氨基-1,8-萘酰亚胺是一个推-拉电子体系的荧光团,通过改变电子供体(通常是共轭氮原子)对共轭体系的供电能力(ICT),就可以实现荧光波长的移动。在本论文中,设计合成了一系列基于ICT原理识别阳离子的1,8-萘酰亚胺类比率荧光探针。利用N-丁基-4-溴-5-硝基-1,8-萘酰亚胺的高反应活性以及5位硝基反应活性远远大于4位溴取代基的特性,向1,8-萘酰亚胺的4,5二位引入不同的阳离子受体,得到了分别针对铜离子、锌离子、镉离子和pH的比率荧光探针。
设计合成了两个系列共15个铜离子比率荧光探针。在CuBF系列中,铜离子的结合减弱了共轭氮原子对荧光团的供电能力,从而引起了荧光波长的蓝移。经过结构的改造,其中CuBF1、CuBF7-11能够在常见金属离子(Li~+,Na~+,K~+,Mg~(2+),Ca~(2+),Fe~(3+),Mn~(2+),Al~(3+),Co~(2+),Ni~(2+),Cu~(2+),Zn~(2+),Cd~(2+),Hg~(2+),Ag~+,Pb~(2+))中专一性的识别铜离子。CuRF系列则是基于脱氢和ICT原理的结合,铜离子与受体的作用能够诱使共轭氮原子上的氢脱去,共轭氮原子显负电增强了对荧光团的供电能力,从而引起荧光波长的红移,同时也造成了吸收光谱的红移。CuRF系列也是专一性的识别铜离子。总结了保证荧光不被铜离子淬灭的两种方法,提出并验证了第三种方法,即受体中含有合适的电子供体,能够补偿铜离子的缺电性,从而阻断铜离子与荧光团之间的电子传递或者能量传递过程,荧光得以保持。在CuBF系列和CuRF系列中,补偿铜离子缺电性的电子供体分别是芳环π电子体系和脱氢后带负电荷的氮原子。
设计合成了两个锌离子比率、比色荧光探针ZnRF1-2。锌离子与ZnRF1-2的作用能够脱去共轭氮原子上的氢,从而使得荧光光谱和吸收光谱发生红移。荧光由黄绿色变成了红色,溶液颜色也由淡黄色变成了粉红色,非常便于可视检测。ZnRF1-2和CuRF系列类似,也是基于脱氢原理和ICT原理的结合。推而广之,这种探针的设计思路可以被运用来设计其他金属离子的比率荧光探针。
Fluorescent probes can transfer molecular recognition events into fluorescence signals and then make a bridge between man and molecule. The advantages of molecular fluorescence for sensing can be summarized: high sensitivity of detection down to the single molecule, "on-off switchability, subnanometer spatial resolution and submillisecond temporal resolution, observation in situ, remote sensing by using optical fibres, et al. Ratiometric fluorescent signals, in contrast with intentisy-responsive ones, have higher sensitivity and can be used in quantitative detection. Ratiometric measurements involve the observation of changes in the ratio of the intensity of the absorption or the emission at two wavelengths. They permit signal rationing and thus increase the dynamic range and provide built-in correction for environmental effects.4-amino-l,8-naphthalimide fluorophore contains an electron-donating group (often an amino group) conjugated to an electron-withdrawing group, it undergoes ICT, intramolecular charge transfer, from the donor to the receptor upon excitation by light. When the electron-donating character is changed, a shift in fluorescence emission spectra would be expected. In this thesis, a series of ratiometric 1,8-naphthalimide fluorescent probes for cations based on the ICT mechanism were designed and synthesized. On the basis of the high reactivity of the precursor N-butyl-4-bromo-5-nitro- 1,8-naphthalimide, we introduced different cation receptors into the 4 and 5 positions, and then obtained ratiometric fluorescent probes for Cu~(2+), Zn~(2+), Cd~(2+), and pH, respectively.Two types of Cu~(2+) ratiometric fluorescent probes, totally including fifteen coupounds, have been designed and synthesized. The binding of Cu~(2+) by CuBF compounds reduces the electron-donating ability of the electron donor. Owing to the reduction of conjugating, a blue shift in emission spectra is observed. Probes CuBF1 and CuBF7-ll exhibit Cu~(2+)-only sensitive among metal ions such as Li~+, Na~+, K~+, Mg~(2+), Ca~(2+), Fe~(3+), Mn~(2+), Al~(3+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Ag~+, Pb~(2+). CuRF coupounds are based on the combination of deprotonation and ICT mechanisms. The secondary amines conjugated to 1,8-naphthalimide could be deprotonated by Cu~(2+), and as a result, large red shifts in both absorption and fluorescence spectra were obtained, from which one could sense Cu~(2+) colorimetrically and ratiometrically. CuRF are also sense only Cu~(2+) among metal ions. Two methods about how to ensure fluorescence not to be quenched by Cu~(2+) have been summarized, and a third one is
presented, that is to compensate the electron-deficiency of Cu2+ with a proper donor. Thus the ET (electron transfer or energy transfer) would be suppressed from fluorophore to copper, and as a result fluorescence is maintained. The donors in CuBF and CuRF are aromatic n electrons and deprotonated nitrogen atoms, respectively.Two ratiometric and colorimetric fluorescent probes ZnRFl-2 for Zn2+ have been designed and synthesized. The secondary amine conjugated to 1,8-naphthalimide could be deprotonated by Zn2+, and as a result, large red shifts in both absorption and fluorescence spectra were obtained, from which one could sense Zn2+ colorimetrically and ratiometrically. These visible emissions, the solutions color changing from piromrose yellow to red and fluorescence from green to red, allow Zn2+ to be readily recognized by the naked eye. Probe ZnRFl-2 for Zn2+ was developed from our former Cu2+ sensors on the base of the same deprotonation mechanism. With the improvement of selectivity for metal ion receptors, we believe that this design strategy would help to extend the development of ratiometric fluorescent probes for other metal ions.Two ratiometric fluorescent probes for Cd2+ CdBFl-2 have been designed and synthesized. The binding of Cd2+ by CdBFl reduced the electron-donating ability of the conjugated nitrogen atom, and blue-shifted the fluorescence emission from 531 nm to 487 nm. However, in the case of Zn2+, the secondary amine conjugated to 1,8-naphthalimide could be deprotonated, and fluorescence emission red-shifted from 531 nm to 558 nm. Thus, CdBFl is a multi-analytes sensing probe.Two fluorescent probes HF1-2 for ratiometric low pH measurements have been designed and synthesized. The two probes have narrow pH-sensitive windows. For HF1 based on ICT mechanism, the fluorescence emission blue-shifted from 566 nm to 522 nm when the solution became more acidic from pH 2.57 to 1.70. In addition, HF1 is non-metal ion sensitive. For HF2 based on intramolecular hydrogen binding, the fluorescence emission red-shifted from 497 nm to 527 nm when the solution became more acidic from pH 2.23 to 1.30.
4-氨基-1,8-萘酰亚胺是一个推-拉电子体系的荧光团,通过改变电子供体(通常是共轭氮原子)对共轭体系的供电能力(ICT),就可以实现荧光波长的移动。在本论文中,设计合成了一系列基于ICT原理识别阳离子的1,8-萘酰亚胺类比率荧光探针。利用N-丁基-4-溴-5-硝基-1,8-萘酰亚胺的高反应活性以及5位硝基反应活性远远大于4位溴取代基的特性,向1,8-萘酰亚胺的4,5二位引入不同的阳离子受体,得到了分别针对铜离子、锌离子、镉离子和pH的比率荧光探针。
设计合成了两个系列共15个铜离子比率荧光探针。在CuBF系列中,铜离子的结合减弱了共轭氮原子对荧光团的供电能力,从而引起了荧光波长的蓝移。经过结构的改造,其中CuBF1、CuBF7-11能够在常见金属离子(Li~+,Na~+,K~+,Mg~(2+),Ca~(2+),Fe~(3+),Mn~(2+),Al~(3+),Co~(2+),Ni~(2+),Cu~(2+),Zn~(2+),Cd~(2+),Hg~(2+),Ag~+,Pb~(2+))中专一性的识别铜离子。CuRF系列则是基于脱氢和ICT原理的结合,铜离子与受体的作用能够诱使共轭氮原子上的氢脱去,共轭氮原子显负电增强了对荧光团的供电能力,从而引起荧光波长的红移,同时也造成了吸收光谱的红移。CuRF系列也是专一性的识别铜离子。总结了保证荧光不被铜离子淬灭的两种方法,提出并验证了第三种方法,即受体中含有合适的电子供体,能够补偿铜离子的缺电性,从而阻断铜离子与荧光团之间的电子传递或者能量传递过程,荧光得以保持。在CuBF系列和CuRF系列中,补偿铜离子缺电性的电子供体分别是芳环π电子体系和脱氢后带负电荷的氮原子。
设计合成了两个锌离子比率、比色荧光探针ZnRF1-2。锌离子与ZnRF1-2的作用能够脱去共轭氮原子上的氢,从而使得荧光光谱和吸收光谱发生红移。荧光由黄绿色变成了红色,溶液颜色也由淡黄色变成了粉红色,非常便于可视检测。ZnRF1-2和CuRF系列类似,也是基于脱氢原理和ICT原理的结合。推而广之,这种探针的设计思路可以被运用来设计其他金属离子的比率荧光探针。
Fluorescent probes can transfer molecular recognition events into fluorescence signals and then make a bridge between man and molecule. The advantages of molecular fluorescence for sensing can be summarized: high sensitivity of detection down to the single molecule, "on-off switchability, subnanometer spatial resolution and submillisecond temporal resolution, observation in situ, remote sensing by using optical fibres, et al. Ratiometric fluorescent signals, in contrast with intentisy-responsive ones, have higher sensitivity and can be used in quantitative detection. Ratiometric measurements involve the observation of changes in the ratio of the intensity of the absorption or the emission at two wavelengths. They permit signal rationing and thus increase the dynamic range and provide built-in correction for environmental effects.4-amino-l,8-naphthalimide fluorophore contains an electron-donating group (often an amino group) conjugated to an electron-withdrawing group, it undergoes ICT, intramolecular charge transfer, from the donor to the receptor upon excitation by light. When the electron-donating character is changed, a shift in fluorescence emission spectra would be expected. In this thesis, a series of ratiometric 1,8-naphthalimide fluorescent probes for cations based on the ICT mechanism were designed and synthesized. On the basis of the high reactivity of the precursor N-butyl-4-bromo-5-nitro- 1,8-naphthalimide, we introduced different cation receptors into the 4 and 5 positions, and then obtained ratiometric fluorescent probes for Cu~(2+), Zn~(2+), Cd~(2+), and pH, respectively.Two types of Cu~(2+) ratiometric fluorescent probes, totally including fifteen coupounds, have been designed and synthesized. The binding of Cu~(2+) by CuBF compounds reduces the electron-donating ability of the electron donor. Owing to the reduction of conjugating, a blue shift in emission spectra is observed. Probes CuBF1 and CuBF7-ll exhibit Cu~(2+)-only sensitive among metal ions such as Li~+, Na~+, K~+, Mg~(2+), Ca~(2+), Fe~(3+), Mn~(2+), Al~(3+), Co~(2+), Ni~(2+), Cu~(2+), Zn~(2+), Cd~(2+), Hg~(2+), Ag~+, Pb~(2+). CuRF coupounds are based on the combination of deprotonation and ICT mechanisms. The secondary amines conjugated to 1,8-naphthalimide could be deprotonated by Cu~(2+), and as a result, large red shifts in both absorption and fluorescence spectra were obtained, from which one could sense Cu~(2+) colorimetrically and ratiometrically. CuRF are also sense only Cu~(2+) among metal ions. Two methods about how to ensure fluorescence not to be quenched by Cu~(2+) have been summarized, and a third one is
presented, that is to compensate the electron-deficiency of Cu2+ with a proper donor. Thus the ET (electron transfer or energy transfer) would be suppressed from fluorophore to copper, and as a result fluorescence is maintained. The donors in CuBF and CuRF are aromatic n electrons and deprotonated nitrogen atoms, respectively.Two ratiometric and colorimetric fluorescent probes ZnRFl-2 for Zn2+ have been designed and synthesized. The secondary amine conjugated to 1,8-naphthalimide could be deprotonated by Zn2+, and as a result, large red shifts in both absorption and fluorescence spectra were obtained, from which one could sense Zn2+ colorimetrically and ratiometrically. These visible emissions, the solutions color changing from piromrose yellow to red and fluorescence from green to red, allow Zn2+ to be readily recognized by the naked eye. Probe ZnRFl-2 for Zn2+ was developed from our former Cu2+ sensors on the base of the same deprotonation mechanism. With the improvement of selectivity for metal ion receptors, we believe that this design strategy would help to extend the development of ratiometric fluorescent probes for other metal ions.Two ratiometric fluorescent probes for Cd2+ CdBFl-2 have been designed and synthesized. The binding of Cd2+ by CdBFl reduced the electron-donating ability of the conjugated nitrogen atom, and blue-shifted the fluorescence emission from 531 nm to 487 nm. However, in the case of Zn2+, the secondary amine conjugated to 1,8-naphthalimide could be deprotonated, and fluorescence emission red-shifted from 531 nm to 558 nm. Thus, CdBFl is a multi-analytes sensing probe.Two fluorescent probes HF1-2 for ratiometric low pH measurements have been designed and synthesized. The two probes have narrow pH-sensitive windows. For HF1 based on ICT mechanism, the fluorescence emission blue-shifted from 566 nm to 522 nm when the solution became more acidic from pH 2.57 to 1.70. In addition, HF1 is non-metal ion sensitive. For HF2 based on intramolecular hydrogen binding, the fluorescence emission red-shifted from 497 nm to 527 nm when the solution became more acidic from pH 2.23 to 1.30.
引文
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