基于氮杂阳离子的分子识别与传感
摘要
氮杂环阳离子特别是咪唑或者吡啶阳离子的一系列衍生物近些年来得到了快速的发展。由于独特的阳离子特征,这类化合物大多应用于阴离子或者生物小分子的识别过程中。在催化领域,咪唑阳离子是氮杂环卡宾(NHCs)的前体,生成的氮杂卡宾金属有机化合物可高效的应用于均相催化反应研究领域。同时,科学家们又开始在二维的基础上衍生到三维立体结构,并形成了一系列具有应用价值的化合物。如何将功能化的单元基团(如：手性,荧光等)引入到该体系中,赋予其更加丰富的性质与应用价值,是目前十分有意义的课题。为解决这些问题本论文进行以下几方面研究：
1.新型氨基萘酰亚胺基阳离子的三臂荧光探针：(1)合成了基于氨基萘酰亚胺功能基团的具有三条咪唑阳离子柔性臂的盘状荧光探针TIA1和TIA2。TIA1能够以荧光增强的方式高选择性地识别全部十二种RNA核苷酸中的ADP,并能够应用于在活体细胞中对核苷酸的荧光成像检测；(2)合成了探针TPA1(以苯环为盘,吡啶阳离子为桥,1,8-萘酰亚胺为发光团的三臂化合物)能够在水体系中通过荧光增强的方式在多种二糖或者单糖中高选择性地识别麦芽糖。TPA1也是首次应用于活体细胞荧光成像的天然糖类荧光探针；(3)探针TIPAl基于咪唑阳离子和哌嗪基团的1,8-萘酰亚胺三臂化合物,能够以荧光增强的方式选择性识别高氯酸铜和硝酸铜离子对。
2.手性环状氮杂卡宾及其配合物的合成及催化研究：以(1R,2R)-(-)-1,2-环己二胺为手性源与对苯二甲醛为原料,通过最终原甲酸三乙酯关环反应合成了一种手性的含三个咪唑啉阳离子的氮杂环卡宾(NHCs)大环型化合物CNHC,并以其为配体首次合成了具有手性性质的氮杂环卡宾-AgI笼状化合物CNHC-Ag,X-射线单晶衍射数据表明,该化合物是由两个配体和三个银离子构成的圆柱状结构,并且进行了CNHC-Ag在D-A反应和胺基硅腈化反应的立体选择性催化研究。通过金属离子中心交换反应,成功的得到了该氮杂卡宾-AuI化合物,通过质谱和核磁证实该金配合物和之前的CNHC-Ag具有相类似的圆柱结构。
3.手性共价二维环状结构衍生至三维笼状结构的设计和构筑：共价二维和三维有机笼状结构在主客体化学、催化、生物酶模拟等方面具有重要应用价值。在手性的含三个咪唑啉阳离子的氮杂环卡宾(NHCs)大环型化合物CNHC研究基础上,本论文设计合成了一系列具有更大空腔和具有良好荧光功能的二维和三维有机共价笼状化合物：(1)手性大环含咪唑啉化合物CNHC2(C63H69N6·3BF4,空腔尺寸：1.4 nm)；(2)具有236 nm大斯托克斯位移的手性多面体笼状化合物CZC(以手性环己二胺为顶角,三氮唑为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.21；(3)具有荧光功能的手性多面体笼状化合物CAC(以手性环己二胺为顶角,三苯胺为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.17；(4)首类四面体笼型化合物CIZ(以Tren为顶角,三苯胺为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.15。通过核磁氢谱、碳谱以及MALDI-TOF等证明了这些化合物的存在,通过理论计算得出空腔体积分别为4200 (?)3、3600 (?)3和1600 (?)3。
Cationic host based N-heterocycle and other related derivatives especially hosts contain cations of imidazole and pyridine have developed rapidly in recent years. These compounds have been widely used in the recognition of ions or small biomolecules because of the unique characters of the cations. In the field of catalyze, imidazoline cations present as the precursor of N-heterocyclic carbenes (NHCs) and thus a large number of metal organic compounds were derived based on it. Numerous studies have been reported owing to their high effective applications in homogeneous catalyzes. Meanwhile, scientists start to do researches on three-dimensional structure derived on the basis of two-dimensional structures and synthesize a series of compounds with interest and potential value. How to design and prepare this system contain functional groups (chirality or fluorescence e.g.) is still a high research value and great importance in supermolecular chemistry. On the basis of this context, this paper contains the following aspects of contents:
1. Tripodal luminescence chemosensors based on 1,8-naphthalimide and imidazolium: (1) We have synthesized flexible tripodal luminescence chemosensors based on functionalized naphthalimide group and three imidazolium or pyridinium cations. Probe TIA1 (preorganized tripodal receptor, imidazolium as bridge and 1,8-naphthalimide as signaling subunits) exhibits a selective "turn-on" fluorescent property for ADP over other ribonucleotide polyphosphates. Probes TIA1 and its derivatives TIA2 then successfully applied in living cells imaging for response ADP; (2) In aqueous media, probe TPA1 (preorganized tripodal receptor, pyridinium cations as bridge and 1,8-naphthalimide as signaling subunits) exhibits a selective "turn-on" fluorescent property for maltose over other saccharides. TPA1 was applied in living cells imaging for response maltose, this is the first luminescence probe sensing carbohydrate in living cells; (3) Probe TIPA1 (preorganized tripodal receptor, imidazolium as bridge, piperazine as recognition site and 1,8-naphthalimide as signaling subunits) acted as a dynamic anion-induced ion-pairs sensor and exhibits a selective "turn-on" fluorescent property for CuⅡion-pair (copper perchlorate and copper nitrate) over a wide range of tested metal ions and Cu2+salts ion pairs.
2. The construction and catalytic performance of the chiral cyclic N-heterocyclic carbenes compounds:Synthesized a chiral N-heterocyclic carbenes (NHCs) macrocycle compound CNHC as ligand, then first assembled a novel chiral N-heterocyclic carbene silver(Ⅰ) cage CNHC-Ag. Single crystal X-ray structural analysis of this complex shows a cylinder-like structure of two ligands and three Ag+ions. CNHC-Ag could be used as a molecular mircoreactor of Diels-Alder reaction to control the enantioselectivity and asymmetric catalysis of strecker reaction. Then we synthesized an Au complex of this ligand by cation exchange reaction. ESI-MS and NMR shows the same structure as CNHC-Ag.
3. Design and synthesis of chiral covalent cage structures derived on the basis of covalent two-dimensional macrocycle structures. Covalent two or three-dimensional organic structures have great value on host-guest chemistry, catalysis, enzyme simulation and so on. Based on the study of chiral N-heterocyclic carbenes (NHCs) macrocycle compound CNHC, this paper synthesized a series of covalent two or three-dimensional compounds, which provide larger cavity and fluorescent function. (1) Chiral imidazolium macrocycle CNHC2 (C63H69N6·3BF4, diameter:1.4 run); (2) Chiral polyhedron cage-like compound CZC (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and triazole as framework) with long wavelength stoke's shift, fluorescence quantum yieldΦf=21; (3) Chiral polyhedron cage-like compound CAC (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and triphenylamine as framework),Φf=0.17; (4) First tetrahedron covalent compound CIZ (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and Tren as framework),Φf=0.15. NMR, MALDI-TOF confirmed the formation of these compounds, the cavity volums calculated by DFT were 4200 A3,3600 A3 and 1600 A3, respectively.
1.新型氨基萘酰亚胺基阳离子的三臂荧光探针：(1)合成了基于氨基萘酰亚胺功能基团的具有三条咪唑阳离子柔性臂的盘状荧光探针TIA1和TIA2。TIA1能够以荧光增强的方式高选择性地识别全部十二种RNA核苷酸中的ADP,并能够应用于在活体细胞中对核苷酸的荧光成像检测；(2)合成了探针TPA1(以苯环为盘,吡啶阳离子为桥,1,8-萘酰亚胺为发光团的三臂化合物)能够在水体系中通过荧光增强的方式在多种二糖或者单糖中高选择性地识别麦芽糖。TPA1也是首次应用于活体细胞荧光成像的天然糖类荧光探针；(3)探针TIPAl基于咪唑阳离子和哌嗪基团的1,8-萘酰亚胺三臂化合物,能够以荧光增强的方式选择性识别高氯酸铜和硝酸铜离子对。
2.手性环状氮杂卡宾及其配合物的合成及催化研究：以(1R,2R)-(-)-1,2-环己二胺为手性源与对苯二甲醛为原料,通过最终原甲酸三乙酯关环反应合成了一种手性的含三个咪唑啉阳离子的氮杂环卡宾(NHCs)大环型化合物CNHC,并以其为配体首次合成了具有手性性质的氮杂环卡宾-AgI笼状化合物CNHC-Ag,X-射线单晶衍射数据表明,该化合物是由两个配体和三个银离子构成的圆柱状结构,并且进行了CNHC-Ag在D-A反应和胺基硅腈化反应的立体选择性催化研究。通过金属离子中心交换反应,成功的得到了该氮杂卡宾-AuI化合物,通过质谱和核磁证实该金配合物和之前的CNHC-Ag具有相类似的圆柱结构。
3.手性共价二维环状结构衍生至三维笼状结构的设计和构筑：共价二维和三维有机笼状结构在主客体化学、催化、生物酶模拟等方面具有重要应用价值。在手性的含三个咪唑啉阳离子的氮杂环卡宾(NHCs)大环型化合物CNHC研究基础上,本论文设计合成了一系列具有更大空腔和具有良好荧光功能的二维和三维有机共价笼状化合物：(1)手性大环含咪唑啉化合物CNHC2(C63H69N6·3BF4,空腔尺寸：1.4 nm)；(2)具有236 nm大斯托克斯位移的手性多面体笼状化合物CZC(以手性环己二胺为顶角,三氮唑为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.21；(3)具有荧光功能的手性多面体笼状化合物CAC(以手性环己二胺为顶角,三苯胺为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.17；(4)首类四面体笼型化合物CIZ(以Tren为顶角,三苯胺为骨架的希夫碱笼状化合物),荧光量子产率为Φf=0.15。通过核磁氢谱、碳谱以及MALDI-TOF等证明了这些化合物的存在,通过理论计算得出空腔体积分别为4200 (?)3、3600 (?)3和1600 (?)3。
Cationic host based N-heterocycle and other related derivatives especially hosts contain cations of imidazole and pyridine have developed rapidly in recent years. These compounds have been widely used in the recognition of ions or small biomolecules because of the unique characters of the cations. In the field of catalyze, imidazoline cations present as the precursor of N-heterocyclic carbenes (NHCs) and thus a large number of metal organic compounds were derived based on it. Numerous studies have been reported owing to their high effective applications in homogeneous catalyzes. Meanwhile, scientists start to do researches on three-dimensional structure derived on the basis of two-dimensional structures and synthesize a series of compounds with interest and potential value. How to design and prepare this system contain functional groups (chirality or fluorescence e.g.) is still a high research value and great importance in supermolecular chemistry. On the basis of this context, this paper contains the following aspects of contents:
1. Tripodal luminescence chemosensors based on 1,8-naphthalimide and imidazolium: (1) We have synthesized flexible tripodal luminescence chemosensors based on functionalized naphthalimide group and three imidazolium or pyridinium cations. Probe TIA1 (preorganized tripodal receptor, imidazolium as bridge and 1,8-naphthalimide as signaling subunits) exhibits a selective "turn-on" fluorescent property for ADP over other ribonucleotide polyphosphates. Probes TIA1 and its derivatives TIA2 then successfully applied in living cells imaging for response ADP; (2) In aqueous media, probe TPA1 (preorganized tripodal receptor, pyridinium cations as bridge and 1,8-naphthalimide as signaling subunits) exhibits a selective "turn-on" fluorescent property for maltose over other saccharides. TPA1 was applied in living cells imaging for response maltose, this is the first luminescence probe sensing carbohydrate in living cells; (3) Probe TIPA1 (preorganized tripodal receptor, imidazolium as bridge, piperazine as recognition site and 1,8-naphthalimide as signaling subunits) acted as a dynamic anion-induced ion-pairs sensor and exhibits a selective "turn-on" fluorescent property for CuⅡion-pair (copper perchlorate and copper nitrate) over a wide range of tested metal ions and Cu2+salts ion pairs.
2. The construction and catalytic performance of the chiral cyclic N-heterocyclic carbenes compounds:Synthesized a chiral N-heterocyclic carbenes (NHCs) macrocycle compound CNHC as ligand, then first assembled a novel chiral N-heterocyclic carbene silver(Ⅰ) cage CNHC-Ag. Single crystal X-ray structural analysis of this complex shows a cylinder-like structure of two ligands and three Ag+ions. CNHC-Ag could be used as a molecular mircoreactor of Diels-Alder reaction to control the enantioselectivity and asymmetric catalysis of strecker reaction. Then we synthesized an Au complex of this ligand by cation exchange reaction. ESI-MS and NMR shows the same structure as CNHC-Ag.
3. Design and synthesis of chiral covalent cage structures derived on the basis of covalent two-dimensional macrocycle structures. Covalent two or three-dimensional organic structures have great value on host-guest chemistry, catalysis, enzyme simulation and so on. Based on the study of chiral N-heterocyclic carbenes (NHCs) macrocycle compound CNHC, this paper synthesized a series of covalent two or three-dimensional compounds, which provide larger cavity and fluorescent function. (1) Chiral imidazolium macrocycle CNHC2 (C63H69N6·3BF4, diameter:1.4 run); (2) Chiral polyhedron cage-like compound CZC (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and triazole as framework) with long wavelength stoke's shift, fluorescence quantum yieldΦf=21; (3) Chiral polyhedron cage-like compound CAC (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and triphenylamine as framework),Φf=0.17; (4) First tetrahedron covalent compound CIZ (Schiff Base cage-like compound with chiral diaminocyclohexane as vertex and Tren as framework),Φf=0.15. NMR, MALDI-TOF confirmed the formation of these compounds, the cavity volums calculated by DFT were 4200 A3,3600 A3 and 1600 A3, respectively.
引文
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