杯[4]芳烃酒石酸衍生物的合成及手性识别
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摘要
超分子化学自组装由于其在药物输送、纳米材料制备、选择性催化,分子识别,手性化合物拆分和生物模拟等方面有着潜在的应用前景,因此引起了广泛的重视,成为当前研究的前沿热点之一。具有洞穴结构、易于衍生化的杯芳烃可包含多种客体分子,而且在自组装方面具有突出的优势。本文合成了一种新的杯[4]芳烃酒石酸衍生物并对其自组装和手性分子识别性能进行了研究,取得了以下一些结果:
1.设计并合成了一种上缘含烷基,下缘为1,3位含L-二苯甲酰酒石酸残基取代的手性杯[4]芳烃酒石酸衍生物5,并且利用核磁共振(NMR)、和红外波谱(IR)对其结构进行了表征和分析。
2.以这种杯[4]芳烃酒石酸衍生物5为主体,发现5与R-α-甲基苄胺在1,2-二氯乙烷中组装成纳米纤维;5与S-α-苯基甘氨醇在3:1的环己烷与1,2-二氯乙烷中有时组装成纳米纤维,有时组装成纳米球;5与(1S,2S)-1,2-二苯基乙二胺在20:1的环己烷和1,2-二氯乙烷中有时组装成纳米纤维,有时组装成纳米球;5与(1R,2S)-2-氨基-1,2-二苯基乙醇在7:1的环己烷和1,2-二氯乙烷中组装成纳米球。
3.通过荧光光谱和核磁共振谱就杯[4]芳烃酒石酸衍生物5对R和S-甲基苄胺,R和S-苯基甘氨醇,(1R,2R)和(1S,2S)-1,2-二苯基乙二胺,(1S,2R)和(1R,2S)-2-氨基-1,2-二苯基乙醇等的分子识别性能进行了研究,结果表明可以通过加入杯芳烃5然后测试溶液荧光变化的方法,实现对这些手性分子的识别,并计算了部分配合物的络合常数。
Supramolecular self-assemblies have potential application in drug delivery, nanomaterial preparation, selective catalysis, or cell mimicry and so on. So supramolecular self-assemblies have attracted great attention from chemists and they are one of topic current interests. Calixarenes can include guest molecules and have much dominance in the field of self-assembly because of their hydrophobic cavities and easy chemical modification. The synthesis, self-assembly and molecular recognition based on a new chiral calix[4]arene tartaric acid derivative have been studied in this thesis. The results conclude the following main points:
1. A new calix[4]arene tartaric acid derivative 5 with alkyl at the upper rim and L- tartaric acid residual substituted in 1, 3 position at the lower rim was designed,synthesized, and characterized by 1HNMR, 13CNMR and IR spectroscopy.
2. (1S, 2S)-1, 2-diphenylethylenediamine,(1R,2S)-2-amino-1,2-diphenylethanol, R-α-methybenzylamine,and S-α-Phenylglycinol could be assembled nanofibers and nanosphere with this calix[4]arene tartaric acid derivative 5. The gelation and turbidity behaviors of the complexes were tested in various organic solvents.
3. The chiral recognition behavior of this chiral calix[4]arene derivative 5 for R /S-α-methybenzylamine, R/S-α-phenylglycinol, (1S,2R)/(1R,2S)-2-aminol-1 ,2-diphenylethanol, (1R,2R)/(1S, 2S)-1, 2-diphenylethylenediamine was studied by Fluorescence spectroscopy and 1HNMR spectroscopy. The results suggest that the recognition of those chiral molecules can be realized by the method that testing the change of Fluorescence intensity after adding calix[4]arene 5 to their soluntion. Meanwhile, Association constants of some complexes were calculated by Fluorescence titration.
1.设计并合成了一种上缘含烷基,下缘为1,3位含L-二苯甲酰酒石酸残基取代的手性杯[4]芳烃酒石酸衍生物5,并且利用核磁共振(NMR)、和红外波谱(IR)对其结构进行了表征和分析。
2.以这种杯[4]芳烃酒石酸衍生物5为主体,发现5与R-α-甲基苄胺在1,2-二氯乙烷中组装成纳米纤维;5与S-α-苯基甘氨醇在3:1的环己烷与1,2-二氯乙烷中有时组装成纳米纤维,有时组装成纳米球;5与(1S,2S)-1,2-二苯基乙二胺在20:1的环己烷和1,2-二氯乙烷中有时组装成纳米纤维,有时组装成纳米球;5与(1R,2S)-2-氨基-1,2-二苯基乙醇在7:1的环己烷和1,2-二氯乙烷中组装成纳米球。
3.通过荧光光谱和核磁共振谱就杯[4]芳烃酒石酸衍生物5对R和S-甲基苄胺,R和S-苯基甘氨醇,(1R,2R)和(1S,2S)-1,2-二苯基乙二胺,(1S,2R)和(1R,2S)-2-氨基-1,2-二苯基乙醇等的分子识别性能进行了研究,结果表明可以通过加入杯芳烃5然后测试溶液荧光变化的方法,实现对这些手性分子的识别,并计算了部分配合物的络合常数。
Supramolecular self-assemblies have potential application in drug delivery, nanomaterial preparation, selective catalysis, or cell mimicry and so on. So supramolecular self-assemblies have attracted great attention from chemists and they are one of topic current interests. Calixarenes can include guest molecules and have much dominance in the field of self-assembly because of their hydrophobic cavities and easy chemical modification. The synthesis, self-assembly and molecular recognition based on a new chiral calix[4]arene tartaric acid derivative have been studied in this thesis. The results conclude the following main points:
1. A new calix[4]arene tartaric acid derivative 5 with alkyl at the upper rim and L- tartaric acid residual substituted in 1, 3 position at the lower rim was designed,synthesized, and characterized by 1HNMR, 13CNMR and IR spectroscopy.
2. (1S, 2S)-1, 2-diphenylethylenediamine,(1R,2S)-2-amino-1,2-diphenylethanol, R-α-methybenzylamine,and S-α-Phenylglycinol could be assembled nanofibers and nanosphere with this calix[4]arene tartaric acid derivative 5. The gelation and turbidity behaviors of the complexes were tested in various organic solvents.
3. The chiral recognition behavior of this chiral calix[4]arene derivative 5 for R /S-α-methybenzylamine, R/S-α-phenylglycinol, (1S,2R)/(1R,2S)-2-aminol-1 ,2-diphenylethanol, (1R,2R)/(1S, 2S)-1, 2-diphenylethylenediamine was studied by Fluorescence spectroscopy and 1HNMR spectroscopy. The results suggest that the recognition of those chiral molecules can be realized by the method that testing the change of Fluorescence intensity after adding calix[4]arene 5 to their soluntion. Meanwhile, Association constants of some complexes were calculated by Fluorescence titration.
引文
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[2]黄志镗,郑企雨.杯芳烃化学的研究,有机化学,2001,21(11):904～913
[3] Arturo Arduini ,Alberto Credi, Giovanni Faimani等Self-Assembly of a Double Calix[6]arene Pseudorotaxane in Oriented Channels.J. Chem. Eur. 2008,14,98～106
[4] Mckinlay. R. M., Atwood. J. L. A Hydrogen-Bonded Hexameric Nanotoroidal Assembly. Angew. Chem. Int. Ed., 2007, 46(1):1～5
[5] Heaven. M. W., Vave. G. W., Mckinlay. R. M., et al. Hydrogen-Bonded Hexamers Self-Assemble as Spherical and tubular superstructures on the Sub-Micron Scale. Angew. Chem. Int. Ed., 2006, 45(37):6221~6224
[6] Byung Hee Hong, Sung Chul Bae, Chi-Wan Lee,et al. Ultrathin Single-Crystalline Silver Nanowire Arrays Formed in an Ambient Solution Phase.Science.2001,294(5441):348～351
[7] Eun Jin Cho,Jeong Ku Kang,Won Seok Han,et al. Stimuli-Responsive Supramolecular Nanostructure from AmphiphilicCalix[4]arene and Its Three-Dimensional Dendritic Silver Nanostructure. J. Am. Chem. Soc.2008,
[8] Vladimir Sidorov,Frank W. Kotch,Mahnaz El-Kouedi,et al.Toward artificial ion channels: self-assembled nanotubes from calix[4]arene–guanosine conjugates. Chem. Commun.2000, 2369~2370
[9] LauraBaldini,Francesco Sansone, Alessandro Casnati. et al,Peptidocalix[4]arene Self-Assembled Nanotubes , Journal of Supramolecular Chemistry. 2002,2: 219~226
[10] Gennady S. Ananchenko, Konstantin A. Udachin,Alix Dubes, John A. Ripmeester, et al. Guest Exchange in Single Crystals of van der Waals Nanocapsules. Angew. Chem. 2006, 118, 1615 ~1618
[11] Gac. S. L., Marrot. J., Reinaud. O., et al. Allosterically Coupled Double InducedFit for1+1+1+1 Self-Assembly of a Calix[6]trisamine, a Calix[6]trisacid and Their Guests. Angew. Chem. Int. Ed., 2006, 45(19):3123~3126
[12] Shoichi Shimizu, Toshiyuki Kiuchi, and Na Pan. A“Teflon-Footed”Resorcinarene: A Hexameric Capsule in Fluorous Solvents and Fluorophobic Effects on Molecular Encapsulation. Angew. Chem. 2007, 119, 6562 ~6565
[13] Oana M. Martin and Sandro Mecozzi. Synthesis and pH-dependent self-assembly of semifluorinated calix[4]arenas.Tetrahedron.2007,63:5539~5547
[14] Myongsoo Lee, Sun-Ja Lee, and Li-HongJiang,Stimuli-ResponsiveSupramolecular Nanocapsules from Amphiphilic Calixarene Assembly.J.Am .Chem.Soc. 2004, 126, 12724~12725
[15] Oshovsky. G. V., Reinhoudt. D. N., Verboom. W. The Underestimated Role of Counter Ions in Electrostatic Self-Assembly: [1+1] Cavitand-Calix[4]arene Capsules Based on Azinium-Sulfonate Interactions. Eur. J. Org. Chem., 2006, 71(7):2810~2816
[16] Atwood. J. L., Barbour. L. J., Jerga. A. Organization of the Interior of Molecular Capsules by Hydrogen Bonding. PNAS., 2002, 99(12):4837~4841
[17] Houmadi. S., Coquiere. D., Legrand. L., et al. Architecture Controller“SMART”Calix[6]arene Self-Assemblies in Aqueous Solution. Langmuir, 2007, 23(9):4849~4855
[18] Casnati. A., Liantonio. R., Metrangolo. P., et al. Molecular and Supramolecular Homochirality Enantiopure Perfluorocarbon Rotamers and Halogen-Bonded Fluorous Double Helices. Angew. Chem.Int. Ed., 2006, 45(12):1915~1918
[19] Tanaka. Y., Miyachi. M., Kobuke. Y. Selective Vesicle Formation form Calixarenes by Self-Assembly. Angew. Chem. Int. Ed., 1999, 38(4):504~506
[20] Olguin. J., Vidal. V. G., Munoz. E., et al. Self-assembly of a Hybrid Organic Inorganic Dicopper(Π) Coordination Polymer With a Calix[4]arene-derived Nitrogenous Ligand. Inorg. Chem. Commun., 2006, 9(3):1096~1098
[21] Mckinlay. R. M., Thallapally. P. K., Cave. G. W. V., et al. Hydrogen-Bonded Supramolecular Assemblies as Robust Templates in the Synthesis of Large Metal-Coordinated Capsules. Angew. Chem. Int. Ed., 2005, 44(35):5733~5736
[22]周稚仙,石雅琳,杜晨霞等.5,11,17,23-四叔丁基-25,26,27,28-四[3-(甲氧基羰基)苄氧基]杯[4]芳烃包合性能的研究.[J].高等学校化学学报,2002,23(12):2281~2283
[23] Zheng Yan-song,Xiao Qin. Chiral Recognition of Carboxylic Acids by Chiral Nitrogen Containing Calix[4]arene. J.Chinese Chemistry.2005,23(10):1289～1291
[24] Xian-Xian Liu,Yan-song Zheng. Chiral nitrogen -containing calix[4]crown—an excellent receptor for chiral recognition of mandelic acid. Tetrahedron Letters.2006,47,6357～6360
[25]杨发福,蔡秀琴,郭红玉等.新型杯[4]芳烃衍生物的合成及其氨基酸萃取性能.[J].分子科学学报,2006,22(2):96~99
[26] Seiji Shirakawa, Akihiro Moriyama, and Shoichi Shimizu. Design of a Novel Inherently Chiral Calix[4]arene for Chiral MolecularRecognition. Org. Lett., 2007,9 (16):3117～3119
[27] SHI, Hui-Jie(史慧杰) SHI, Xian-Fa(施宪法) YAO, Tian-Ming(姚天明),et al. Study of the Molecular Recognition of Nucleotides and Bases by a Novel Calixarene Derivative Containing Uracil. J.Chinese Chemistry, 2008, 26, 170~174
[28] Tommaso Mecca ,Francesca Cunsolo. Calix[4]arene-based ligands as endotoxin receptors. Tetrahedron .2007,63, 10764~10767
[29] Zhi Liang, Zhilian Liu and Yunhua Gao. A selective colorimetric chemosensor based on calixarene framework for lanthanide ions-Dy3+ and Er3+.Tetrahedron Letters. 2007, 48, 3587~3590
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