反应型氰离子和硫醇探针合成及光谱研究
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摘要
氰化物是医药、合成树脂、杀虫剂、化肥、农药等的重要原料,同时还是冶金、镀金工业用的一种重要试剂。但氰化物属于剧毒物质,对人的中毒量及致死量极微,除了直接误服外,其粉尘和蒸汽也能通过消化道或呼吸道进入人体,甚至能渗入人和动物的皮肤,与体内细胞色素氧化酶中的三价铁结合,从而使人和动物的细胞不能获取氧,失去了传递氧的作用,使机体缺乏氧,导致中毒甚至造成内窒息死亡因此,研究微量氰根的测定方法在环境监测和食品分析中非常重要。长期以来,人们就其定量方法做出了大量的研究。传统的氰根离子的识别主要是通过氰根与探针之间的氢键作用,但是存在着选择性差的缺陷。本文主要是选择香豆素和蒽作为发光基团,1,3-茚满二酮和苯并[b]噻吩-3(2H)-酮1,1-二氧化物作为受体,设计合成了一系列的荧光化学传感器,用于识别氰根离子。
另一方面,硫醇在结构上含有强亲核性的巯基,在性质上和氰离子一样,也能和α,β-不饱和双键发生1,4-加成反应,实现对硫醇的专一识别。生物硫醇如半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)在维持细胞新陈代谢和氧化还原平衡等众多生理过程中扮演着重要的角色。细胞内硫醇水平的改变与很多疾病密切相关,如牛皮癣、癌症和艾滋病。体内缺乏半胱氨酸(Cys)会导致很多病症,如儿童生长缓慢,皮肤损伤,头发掉色,肝脏水肿。血液中高浓度的同型半胱氨酸(Hcy)是冠心病和脑梗塞的独立致病因素。谷胱甘肽(GSH)是细胞内最富裕的非蛋白质硫醇,在维持细胞的氧化还原动态平衡中起着重要作用,而且谷胱甘肽的水平还与许多疾病和癌症有着直接的联系。因此,定量检测生物体系中硫醇的浓度在生物化学和临床化学中具有重要意义。该部分主要是选择香豆素作为发光基团,苯并[b]噻吩-3(2H)-酮1,1-二氧化物作为受体,设计合成了一种的比色化学传感器,用于识别硫醇。
本论文主要的内容如下所述：
第一章,重点介绍了化学传感器的原理,并对于氰根离子和硫醇的检测进展进行了综述,最后提出了本文的主要研究内容。
第二章,以香豆素为发光基团,1,3-茚满二酮为受体,合成了一种香豆素-1,3-茚满二酮的加合物(2-1)。化合物2-1能够在乙腈中,氰离子和化合物2-1发生迈克加成反应,荧光光谱上表现为一种比率荧光变化,同时显示了快速响应性和高选择性。化合物2-1分子内存在着强的分子内电荷转移效应(ICT),当氰根离子加成以后,分子内的共轭体系遭到破坏,ICT终止,紫外-可见光谱和荧光光谱上都有明显的比率变化。同时溶液颜色由粉红色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。此外,研究了分子结构中含有吸电子的硝基基团(2-2)的影响。
第三章,以香豆素为发光基团,苯并[b]噻吩-3(2H)-酮1,1-二氧化物为受体,合成了一种香豆素-苯并[b]噻吩-3(2H)-酮1,1-二氧化物(3-1)。化合物3-1能够在乙腈中,氰根离子和化合物3-1发生迈克加成反应,荧光光谱上表现为一种比率荧光变化,同时显示了快速响应性和高选择性。化合物3-1分子内存在着强的ICT效应,当氰根离子加成以后,分子内的共轭体系遭到破坏,ICT终止,紫外-可见光谱和荧光光谱上都有明显的比率变化。同时溶液颜色由粉红色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。
第四章,以蒽为发光基团,1,3-茚满二酮为受体,合成了一种香豆素-1,3-茚满二酮(4-1)。化合物4-1能够在乙腈中,氰根离子和化合物4-1发生迈克加成反应,荧光光谱上表现为一种双发射增强型变化,同时显示了快速响应性和高选择性。化合物4-1整个分子处于一个共轭体系,当氰根离子加成以后,分子内的共轭体系遭到破坏,但分子结构变得更加柔性,分子更容易发生折叠,光照下,分子内部形成激基复合物(Exciplex),分子内的光诱导电子转移(PET)终止,荧光光谱上都有明显的变化。同时溶液颜色由黄色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。
第五章,化合物2-1,3-1能够在DMSO-PBS buffer (0.01M, pH=7.4,9:1, v/v)体系中,和硫醇发生迈克加成反应,紫外-可见光谱上表现为一种比率型变化,同时显示了快速响应性和高选择性。化合物2-1,3-1分子内存在着强的ICT效应,当硫醇加成以后,分子内的共轭体系遭到破坏,分子内的电荷转移(ICT)终止,紫外-可见光谱上都有明显的蓝移。同时溶液颜色由紫蓝色变成无色。
Among various anions, cyanide is one of the most concerned anions because of its being widely used in synthetic fibers, resins, herbicide, and the gold-extraction process. However, cyanide anion is extremely detrimental, and could be absorbed through lungs, gastrointestinal track and skin, leading to vomiting, convulsion, loss of consciousness, and eventual death. Thus, there is a need for an efficient sensing system to monitor cyanide concentration from contaminant sources. Due to the importance of cyanide in environment, the design and synthesis of efficient cyanide receptors attracts intensive interests of scientists and have become a significant subject in the field of supramolucular chemistry. However, the traditional cyanide synthetic receptors or sensors on the basis of hydrogen bonding interactions show poor selectivity due to the presence of F-, AcO-, CO32-, HCO3-, HSO4-, and H2PO4-which often display the strong interference to cyanide detection. In this dissertation, three novel fluorescent probes with coumarin and anthracene as fluorophores and1,3-indanedione and benzo[b]thiophene-3(2H)-one1,1-dioxide as receptors for cyanide were designed and synthesized.
On the other hand, considering the similar strong nucleophility of the thiols and cyanide, we were thinking that the conjugate1,4-addition of thiols to unsaturated bond could be used for the detection of thiol with high selectivity. Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in many physiological processes. Alternations in the level of cellular thiols have been linked to a number of diseases, such as cardiovascular disease, Alzheimer's disease, leucocyte loss, psoriasis, liver damage, cancer, and AIDS. Thus, it is important to develop efficient methods for the detection and quantification of biothiols in physiological media for academic research and clinic applications. Due to their simplicity, inexpensiveness, sensitivity and selectivity, optical approach based on synthetic colorimetric and fluorescent probes has attracted increasing interest during the last decade. In the last part of this dissertation, a novel fluorescent probe with coumarin as fluorophore and benzo[b]thiophene-3(2H)-one1,1-dioxide as receptor for thiol was designed and synthesized.
The main contents and results are outlined as follows:
In chapter1, the major sensing principles of optical chemosensors are introduced, and the progress of cyanide recognition and thiol detection is reviewed. Finally, the objective of this dissertation was proposed.
In chapter2, a ratiometric fluorescent probe (2-1) based on coumarin-indandione conjugate was synthesized for cyanide detection. A colorimetricand ratiometric fluorescent probe (2-1) for the detection of cyanide ion based on the1,4-addition reaction of cyanide ion to indandione moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to indandione of2-1would block the ICT from the electron-rich coumarin group to the electron-poor indandione group, leading to a blue shift in the absorption spectra and emission spectra with an observed color change (from pink to colorless). The1:1binding stoichiometry for the compound2-1with cyanide ion was confirmed by HRMS, and the proposed mechanism was confirmed by1HNMR. Additionally, compound2-2with a nitro group was designed and synthesized as a control compound for investigating the substituent effect.
In chapter3, a ratiometric fluorescent probe (3-1) based on coumarin-benzo[b]thiophene-3(2H)-one1,1-dioxide conjugate was synthesized for cyanide detection. A colorimetric and ratiometric fluorescent probe (3-1) for the detection of cyanide ion based on the1,4-addition reaction of cyanide ion to benzo[b]thiophene-3(2H)-one1,1-dioxide moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to benzo[b]thiophene-3(2H)-one1,1-dioxide of3-1would block the ICT from the electron-rich coumarin group to the electron-poor benzo[b]thiophene-3(2H)-one1,1-dioxide group, leading to a blue shift in the absorption spectra and emission spectra with an observed color change(from pink to colorless). The1:1binding stoichiometry for the compound3-1with cyanide ion was proven by HRMS, and the proposed mechanism was confirmed by1HNMR.
In chapter4, a turn-on fluorescent probe (4-1) based on anthracene-indanedione conjugate was synthesized for cyanide detection. A colorimetric (from yellow to colorless) and turn-on fluorescent probe (4-1) for the detection of cyanide ion based on the 1,4-addition reaction of cyanide ion to indandione moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to indandione of4-1would block the π-conjugation of the molecule and the whole molecular structure becomes flexible, which makes it easy for the two parts of the compound to fold. Consequently, light excitation may induce the interaction of1,3-indandione anion with anthracene, leading to exciplex formation. In addition, the fluorescence enhancement at short wavelength (467nm) is probably a result of the inhibition of PET quenching from the anthracene to the indandione-containing Michael receptor upon addition of cyanide. The1:1binding stoichiometry for the compound4-1with cyanide ion was proven by job'plot and by HRMS, and the proposed mechanism was confirmed by1HNMR.
In chapter5, two colorimetric probes for the detection of thiol based on the1,4-addition reaction of thiol to indandione moiety in DMSO-PBS buffer, exhibit fast response and high selectivity toward thiol over other amino acids. The Michael addition of thiol to2-1or3-1would block the ICT from the electron-rich coumarin group to the electron-poor1,3-indandione or benzo[b]thiophene-3(2H)-one1,1-dioxide group, leading to a blue shift in the absorption spectra with an observed color change(from bluevoilet to colorless).
另一方面,硫醇在结构上含有强亲核性的巯基,在性质上和氰离子一样,也能和α,β-不饱和双键发生1,4-加成反应,实现对硫醇的专一识别。生物硫醇如半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)在维持细胞新陈代谢和氧化还原平衡等众多生理过程中扮演着重要的角色。细胞内硫醇水平的改变与很多疾病密切相关,如牛皮癣、癌症和艾滋病。体内缺乏半胱氨酸(Cys)会导致很多病症,如儿童生长缓慢,皮肤损伤,头发掉色,肝脏水肿。血液中高浓度的同型半胱氨酸(Hcy)是冠心病和脑梗塞的独立致病因素。谷胱甘肽(GSH)是细胞内最富裕的非蛋白质硫醇,在维持细胞的氧化还原动态平衡中起着重要作用,而且谷胱甘肽的水平还与许多疾病和癌症有着直接的联系。因此,定量检测生物体系中硫醇的浓度在生物化学和临床化学中具有重要意义。该部分主要是选择香豆素作为发光基团,苯并[b]噻吩-3(2H)-酮1,1-二氧化物作为受体,设计合成了一种的比色化学传感器,用于识别硫醇。
本论文主要的内容如下所述：
第一章,重点介绍了化学传感器的原理,并对于氰根离子和硫醇的检测进展进行了综述,最后提出了本文的主要研究内容。
第二章,以香豆素为发光基团,1,3-茚满二酮为受体,合成了一种香豆素-1,3-茚满二酮的加合物(2-1)。化合物2-1能够在乙腈中,氰离子和化合物2-1发生迈克加成反应,荧光光谱上表现为一种比率荧光变化,同时显示了快速响应性和高选择性。化合物2-1分子内存在着强的分子内电荷转移效应(ICT),当氰根离子加成以后,分子内的共轭体系遭到破坏,ICT终止,紫外-可见光谱和荧光光谱上都有明显的比率变化。同时溶液颜色由粉红色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。此外,研究了分子结构中含有吸电子的硝基基团(2-2)的影响。
第三章,以香豆素为发光基团,苯并[b]噻吩-3(2H)-酮1,1-二氧化物为受体,合成了一种香豆素-苯并[b]噻吩-3(2H)-酮1,1-二氧化物(3-1)。化合物3-1能够在乙腈中,氰根离子和化合物3-1发生迈克加成反应,荧光光谱上表现为一种比率荧光变化,同时显示了快速响应性和高选择性。化合物3-1分子内存在着强的ICT效应,当氰根离子加成以后,分子内的共轭体系遭到破坏,ICT终止,紫外-可见光谱和荧光光谱上都有明显的比率变化。同时溶液颜色由粉红色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。
第四章,以蒽为发光基团,1,3-茚满二酮为受体,合成了一种香豆素-1,3-茚满二酮(4-1)。化合物4-1能够在乙腈中,氰根离子和化合物4-1发生迈克加成反应,荧光光谱上表现为一种双发射增强型变化,同时显示了快速响应性和高选择性。化合物4-1整个分子处于一个共轭体系,当氰根离子加成以后,分子内的共轭体系遭到破坏,但分子结构变得更加柔性,分子更容易发生折叠,光照下,分子内部形成激基复合物(Exciplex),分子内的光诱导电子转移(PET)终止,荧光光谱上都有明显的变化。同时溶液颜色由黄色变成无色。主客体之间是通过1：1的化学计量比进行反应的,加成产物通过核磁滴定和高分辨质谱得以证实。
第五章,化合物2-1,3-1能够在DMSO-PBS buffer (0.01M, pH=7.4,9:1, v/v)体系中,和硫醇发生迈克加成反应,紫外-可见光谱上表现为一种比率型变化,同时显示了快速响应性和高选择性。化合物2-1,3-1分子内存在着强的ICT效应,当硫醇加成以后,分子内的共轭体系遭到破坏,分子内的电荷转移(ICT)终止,紫外-可见光谱上都有明显的蓝移。同时溶液颜色由紫蓝色变成无色。
Among various anions, cyanide is one of the most concerned anions because of its being widely used in synthetic fibers, resins, herbicide, and the gold-extraction process. However, cyanide anion is extremely detrimental, and could be absorbed through lungs, gastrointestinal track and skin, leading to vomiting, convulsion, loss of consciousness, and eventual death. Thus, there is a need for an efficient sensing system to monitor cyanide concentration from contaminant sources. Due to the importance of cyanide in environment, the design and synthesis of efficient cyanide receptors attracts intensive interests of scientists and have become a significant subject in the field of supramolucular chemistry. However, the traditional cyanide synthetic receptors or sensors on the basis of hydrogen bonding interactions show poor selectivity due to the presence of F-, AcO-, CO32-, HCO3-, HSO4-, and H2PO4-which often display the strong interference to cyanide detection. In this dissertation, three novel fluorescent probes with coumarin and anthracene as fluorophores and1,3-indanedione and benzo[b]thiophene-3(2H)-one1,1-dioxide as receptors for cyanide were designed and synthesized.
On the other hand, considering the similar strong nucleophility of the thiols and cyanide, we were thinking that the conjugate1,4-addition of thiols to unsaturated bond could be used for the detection of thiol with high selectivity. Biothiols such as cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play crucial roles in many physiological processes. Alternations in the level of cellular thiols have been linked to a number of diseases, such as cardiovascular disease, Alzheimer's disease, leucocyte loss, psoriasis, liver damage, cancer, and AIDS. Thus, it is important to develop efficient methods for the detection and quantification of biothiols in physiological media for academic research and clinic applications. Due to their simplicity, inexpensiveness, sensitivity and selectivity, optical approach based on synthetic colorimetric and fluorescent probes has attracted increasing interest during the last decade. In the last part of this dissertation, a novel fluorescent probe with coumarin as fluorophore and benzo[b]thiophene-3(2H)-one1,1-dioxide as receptor for thiol was designed and synthesized.
The main contents and results are outlined as follows:
In chapter1, the major sensing principles of optical chemosensors are introduced, and the progress of cyanide recognition and thiol detection is reviewed. Finally, the objective of this dissertation was proposed.
In chapter2, a ratiometric fluorescent probe (2-1) based on coumarin-indandione conjugate was synthesized for cyanide detection. A colorimetricand ratiometric fluorescent probe (2-1) for the detection of cyanide ion based on the1,4-addition reaction of cyanide ion to indandione moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to indandione of2-1would block the ICT from the electron-rich coumarin group to the electron-poor indandione group, leading to a blue shift in the absorption spectra and emission spectra with an observed color change (from pink to colorless). The1:1binding stoichiometry for the compound2-1with cyanide ion was confirmed by HRMS, and the proposed mechanism was confirmed by1HNMR. Additionally, compound2-2with a nitro group was designed and synthesized as a control compound for investigating the substituent effect.
In chapter3, a ratiometric fluorescent probe (3-1) based on coumarin-benzo[b]thiophene-3(2H)-one1,1-dioxide conjugate was synthesized for cyanide detection. A colorimetric and ratiometric fluorescent probe (3-1) for the detection of cyanide ion based on the1,4-addition reaction of cyanide ion to benzo[b]thiophene-3(2H)-one1,1-dioxide moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to benzo[b]thiophene-3(2H)-one1,1-dioxide of3-1would block the ICT from the electron-rich coumarin group to the electron-poor benzo[b]thiophene-3(2H)-one1,1-dioxide group, leading to a blue shift in the absorption spectra and emission spectra with an observed color change(from pink to colorless). The1:1binding stoichiometry for the compound3-1with cyanide ion was proven by HRMS, and the proposed mechanism was confirmed by1HNMR.
In chapter4, a turn-on fluorescent probe (4-1) based on anthracene-indanedione conjugate was synthesized for cyanide detection. A colorimetric (from yellow to colorless) and turn-on fluorescent probe (4-1) for the detection of cyanide ion based on the 1,4-addition reaction of cyanide ion to indandione moiety in CH3CN, exhibits fast response and high selectivity toward cyanide ion over other anions. The Michael addition of cyanide to indandione of4-1would block the π-conjugation of the molecule and the whole molecular structure becomes flexible, which makes it easy for the two parts of the compound to fold. Consequently, light excitation may induce the interaction of1,3-indandione anion with anthracene, leading to exciplex formation. In addition, the fluorescence enhancement at short wavelength (467nm) is probably a result of the inhibition of PET quenching from the anthracene to the indandione-containing Michael receptor upon addition of cyanide. The1:1binding stoichiometry for the compound4-1with cyanide ion was proven by job'plot and by HRMS, and the proposed mechanism was confirmed by1HNMR.
In chapter5, two colorimetric probes for the detection of thiol based on the1,4-addition reaction of thiol to indandione moiety in DMSO-PBS buffer, exhibit fast response and high selectivity toward thiol over other amino acids. The Michael addition of thiol to2-1or3-1would block the ICT from the electron-rich coumarin group to the electron-poor1,3-indandione or benzo[b]thiophene-3(2H)-one1,1-dioxide group, leading to a blue shift in the absorption spectra with an observed color change(from bluevoilet to colorless).
引文
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