芳环类超分子化合物的合成及分子识别研究
|
摘要
第一章CTV类化合物和穴番类化合物同属于芳环类超分子化合物,能通过氢键、疏水、π-π及包合等作用和中性小分子形成包合物,是一类重要的超分子主体化合物。本章简要综述了CTV类化合物和穴番类化合物的结构特点,详细介绍了它们的合成方法、分子识别功能及研究现状。
第二章以香草醛为原料,分别与硫酸二甲酯、硫酸二乙酯和溴代正丙烷反应,所得产物再用硼氢化钠还原成藜芦醇,最后用三聚缩合反应法合成了2,3,7,8,12,13-六甲氧基-10,15-二氢-三苯环壬烷(CTV),2,7,12-三乙氧基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含乙氧基CTV),2,7,12-三丙氧基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含丙氧基CTV)三种CTV类化合物,将三种CTV类化合物分别用无水三氯化铝进行去甲基化反应,生成2,7,12-三羟基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含羟基CTV),并比较它们的产率,分别为78%,55%,10%,结果表明用CTV做原料去甲基化生成含羟基CTV的产率最高。用核磁和红外光谱对所有化合物的结构进行了表征,并考察了这些化合物在不同极性有机溶剂中的紫外和荧光光谱特征。
第三章以香草醛为原料,无水乙醇作溶剂和1,3-二溴丙烷反应生成1,3-二(4-甲酰-2-甲氧基苯基)丙烷,再用硼氢化钠进行还原反应生成1,3-二溴丙烷反应生成1,3-二(4-羟甲基-2-甲氧基苯基)丙烷,最后在高度稀释的酸性催化条件下用二次三聚缩合反应合成了穴番-E,产物通过硅胶柱分离纯化后用核磁对其结构进行了表征,并考察了其在各种有机溶剂中的紫外和荧光基本特征,筛选出了适用于穴番-E对小分子识别研究的乙酸乙酯、二氧六环、乙腈溶剂,在这些溶剂中穴番-E有良好的溶解性,光谱信号明显。
第四章采用紫外、荧光光谱法分别在乙酸乙酯、二氧六环、乙腈溶剂中研究了穴番-E与中性小分子CH_2Cl_2、CHCl_3的相互作用。研究结果表明:在同一种溶剂中穴番-E对三氯甲烷有较强的识别能力,形成了1:1包合的主客体包合物,采用双倒数曲线和非线性拟合方法计算了包合常数。在乙酸乙酯中穴番-E对三氯甲烷的包合效果最好,其次是二氧六环和乙腈,说明溶剂对穴番-E的包合能力有一定的影响。计算机模拟分子力学和空间匹配原则进一步证实穴番-E和三氯甲烷能形成稳定的主客体包合物。研究还发现,穴番-E和二氯甲烷的作用很弱,非线性拟合方法计算所得包合常数表明,穴番-E和二氯甲烷有微弱的包合作用,可能是由于二氯甲烷的体积比较小,与穴番-E的空腔在尺寸上不匹配。
Chapter 1:Cyclotriveratrylenes(CTV) and cryptophanes are classified as aromatic ring compounds,They are a type important of supramolecular, because they can recognize ions and molecules via electrostatic, hydrogen-bonding,hydrophobic,π-πand inclusion interactions.This chapter reviewed the history,structural feature,synthesis method,research status and recognition interaction of cyclotriveratrylenes and cryptophanes.
Chapter 2:Three kinds of CTV and cyclotriveratrylene,2,7,12-triethoxy-3, 8,13-trimethoxy-10,15-dihydro-5H-tribenzo-[a d g]cyclononene(CTV with triethoxy substituent),2,7,12-tripropoxy-3,8,13-trimethoxy-10, 15-dihydro-5H- tribenzo-[a d g]cyclononene(CTV with tripropoxy substituent) were synthesized from vanillin using a trimerization reaction method according to the literature.2,7,12-trihydroxy-3,8,13-trimethoxy-10, 15-dihydro-5H-tribenzo-[a d g]cyclononene(CTV with trihydroxy substituent) was abtained from three kinds of CTV compounds respectively reacting with aluminium chloride anhydrous.The output of CTV with trihydroxy substituent from CTV was maximum by comparing the field. Their chemical structures were confirmed by NMR.The absorption and fluorescence spectroscopic properties of CTV analogues and derivatives different organic solvents were determined,and their structural characteristics and luminescence mechanism were explored in depth.The work fills the gaps in the basic spectral data for CTV compounds and provides a certain theoretical basis for later studying on the molecular recognition.
Chapter 3:Cryptophane-E was synthesized from 1,3-bis(4-hydroxymethyl-2-methoxyphenoxy) propane using twice trimerization reaction by warming a highly diluted solution in a formic acid.The vanillyl alcohol was abtained by reacting vanillin with 1,3-dibromopropane.It was purified by elution through a silica gel column and characterized by nuclear magnetic resonance(NMR) spectroscopy.The spectroscopic properties of cryptophane-E in different organic solvents were reviewed and solvent and concentration effects were studied.
Chapter 4:The interaction of cryptophane-E with CHCl_3 and CH_2Cl_2 was studied in detail by absorption and fluorescence spectroscopies.The results showed that cryptophane-E and CHCl_3 formed a stable 1:1 host-guest inclusion complex,The binding constants were determined by Benesi-Hildebrand equation and the nonlinear least squares fit method.The binding affinity of cryptophane-E with CHCl_3 is the largest in ethyl acetate, followed by dioxane and acetonitrile.In addition,the effect of guest volume on the host-guest inclusion complex was investigated.It shows that guest molecules CH_2Cl_2 were unable to form inclusion complex with cryptophane-E due to its sizes mismatching with the host cavity.The results were further confirmed by the molecular dynamic calculation and the occupancy factors.
第二章以香草醛为原料,分别与硫酸二甲酯、硫酸二乙酯和溴代正丙烷反应,所得产物再用硼氢化钠还原成藜芦醇,最后用三聚缩合反应法合成了2,3,7,8,12,13-六甲氧基-10,15-二氢-三苯环壬烷(CTV),2,7,12-三乙氧基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含乙氧基CTV),2,7,12-三丙氧基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含丙氧基CTV)三种CTV类化合物,将三种CTV类化合物分别用无水三氯化铝进行去甲基化反应,生成2,7,12-三羟基-3,8,13-三甲氧基-10,15-二氢-三苯环壬烷(含羟基CTV),并比较它们的产率,分别为78%,55%,10%,结果表明用CTV做原料去甲基化生成含羟基CTV的产率最高。用核磁和红外光谱对所有化合物的结构进行了表征,并考察了这些化合物在不同极性有机溶剂中的紫外和荧光光谱特征。
第三章以香草醛为原料,无水乙醇作溶剂和1,3-二溴丙烷反应生成1,3-二(4-甲酰-2-甲氧基苯基)丙烷,再用硼氢化钠进行还原反应生成1,3-二溴丙烷反应生成1,3-二(4-羟甲基-2-甲氧基苯基)丙烷,最后在高度稀释的酸性催化条件下用二次三聚缩合反应合成了穴番-E,产物通过硅胶柱分离纯化后用核磁对其结构进行了表征,并考察了其在各种有机溶剂中的紫外和荧光基本特征,筛选出了适用于穴番-E对小分子识别研究的乙酸乙酯、二氧六环、乙腈溶剂,在这些溶剂中穴番-E有良好的溶解性,光谱信号明显。
第四章采用紫外、荧光光谱法分别在乙酸乙酯、二氧六环、乙腈溶剂中研究了穴番-E与中性小分子CH_2Cl_2、CHCl_3的相互作用。研究结果表明:在同一种溶剂中穴番-E对三氯甲烷有较强的识别能力,形成了1:1包合的主客体包合物,采用双倒数曲线和非线性拟合方法计算了包合常数。在乙酸乙酯中穴番-E对三氯甲烷的包合效果最好,其次是二氧六环和乙腈,说明溶剂对穴番-E的包合能力有一定的影响。计算机模拟分子力学和空间匹配原则进一步证实穴番-E和三氯甲烷能形成稳定的主客体包合物。研究还发现,穴番-E和二氯甲烷的作用很弱,非线性拟合方法计算所得包合常数表明,穴番-E和二氯甲烷有微弱的包合作用,可能是由于二氯甲烷的体积比较小,与穴番-E的空腔在尺寸上不匹配。
Chapter 1:Cyclotriveratrylenes(CTV) and cryptophanes are classified as aromatic ring compounds,They are a type important of supramolecular, because they can recognize ions and molecules via electrostatic, hydrogen-bonding,hydrophobic,π-πand inclusion interactions.This chapter reviewed the history,structural feature,synthesis method,research status and recognition interaction of cyclotriveratrylenes and cryptophanes.
Chapter 2:Three kinds of CTV and cyclotriveratrylene,2,7,12-triethoxy-3, 8,13-trimethoxy-10,15-dihydro-5H-tribenzo-[a d g]cyclononene(CTV with triethoxy substituent),2,7,12-tripropoxy-3,8,13-trimethoxy-10, 15-dihydro-5H- tribenzo-[a d g]cyclononene(CTV with tripropoxy substituent) were synthesized from vanillin using a trimerization reaction method according to the literature.2,7,12-trihydroxy-3,8,13-trimethoxy-10, 15-dihydro-5H-tribenzo-[a d g]cyclononene(CTV with trihydroxy substituent) was abtained from three kinds of CTV compounds respectively reacting with aluminium chloride anhydrous.The output of CTV with trihydroxy substituent from CTV was maximum by comparing the field. Their chemical structures were confirmed by NMR.The absorption and fluorescence spectroscopic properties of CTV analogues and derivatives different organic solvents were determined,and their structural characteristics and luminescence mechanism were explored in depth.The work fills the gaps in the basic spectral data for CTV compounds and provides a certain theoretical basis for later studying on the molecular recognition.
Chapter 3:Cryptophane-E was synthesized from 1,3-bis(4-hydroxymethyl-2-methoxyphenoxy) propane using twice trimerization reaction by warming a highly diluted solution in a formic acid.The vanillyl alcohol was abtained by reacting vanillin with 1,3-dibromopropane.It was purified by elution through a silica gel column and characterized by nuclear magnetic resonance(NMR) spectroscopy.The spectroscopic properties of cryptophane-E in different organic solvents were reviewed and solvent and concentration effects were studied.
Chapter 4:The interaction of cryptophane-E with CHCl_3 and CH_2Cl_2 was studied in detail by absorption and fluorescence spectroscopies.The results showed that cryptophane-E and CHCl_3 formed a stable 1:1 host-guest inclusion complex,The binding constants were determined by Benesi-Hildebrand equation and the nonlinear least squares fit method.The binding affinity of cryptophane-E with CHCl_3 is the largest in ethyl acetate, followed by dioxane and acetonitrile.In addition,the effect of guest volume on the host-guest inclusion complex was investigated.It shows that guest molecules CH_2Cl_2 were unable to form inclusion complex with cryptophane-E due to its sizes mismatching with the host cavity.The results were further confirmed by the molecular dynamic calculation and the occupancy factors.
引文
[1]PEDERSEN C J.The discovery of crown ethers[J].Angew.Chem.Int.Ed.Engl.,1988,27(8):1021-1027.
[2]CRAM D.The design of molecular hosts,guests,and their complexes[J].Angew Chem.Int.Ed.Engl.,1988,27(8):1009-1020.
[3]LEHN J M.Supramolecular chemistry-scope and perspectives molecules,supermolecules,and molecular devices[J].Angew.Chem.,Int.Ed.Engl.,1988,27(1):89-112.
[4]DOMINIK A,ROTH H J,SCHIERBAUM K D,GOPEL W.Supramolecular complexes based on calixarenes:force field calculations and applications for chemical sensors[J].Supramolecular Science,1994,1:11-19.
[5]SCHNEIDER H J,YATSIMIRSKY A.Principles and methods in supramolecular Chemistry.Chichester:Wiley,1999,225-230.
[6]OSHITA K,TAKAYANAGI T,OSHIMA M,MOTOMIZU S.Complex formation analysis of water-soluble calixarenes by capillary zone electrophoresis[J].Journal of Chromatography A,2001,934:113-122.
[7]LEHN J M.Comprehensive supramolecular chemistry.Oxford:Pergamon,1996,1:30-34.
[8]沈家骢,孙俊奇.超分子科学研究进展[J].中国科学院院刊,2004,19:420-424.
[9]NIDAN G,NIEL M-A.Electride modified by sulfonated calixarenes immobilized into a polypyrrole filem:a step towards new ion-sensitive layer[J].Synthetic metal,1997,84:225-256.
[10]ZHONG Z L,CHEN Y Y,LU X R.Calix[4]arenas and double calix[4]arenes bridged via calixarenes segments[J].Tetrahedron Letters,1995,36:6735-6738.
[11]MNUK P,FELEL L,SCHURIG V.Gas chromatographic study of the inclusion properties of calixarenes[J].Journal of Chromatography,1996,732:63-74.
[12]Robinson G M.A reaction of homopiperonyl and of homoveratryl alcohols[J].J.Chem.Soc.,Trans.,1915,107:267-276.
[13]EWINS A J.The action of phosphorus pentachloride on the methylene ethers of catechol.Part Ⅴ.of protocatechuyl alcohol and protocatechuonitrile[J].J.Chem. Soc.,Trans.,1909,95:1482-1488.
[14]White J D,Gesner B D.Cyclotetraveratrylene,a conformationally mobile structure[J].Tetrahedron Lett.,1968,9(13):1591-1594.
[15]ERDTMAN H,HAGLID F,RYHAGE R.Macrocyclic condensation products of veratrole and resorcinol[J].Acta.Chem.Scand.,1964,18:1249-1254.
[16]ZIMMERMANN H,TOLSTOY P,LIMBACH H,POUPKO R,LUZ Z.The saddle form of cyclotriveratrylene[J].J.Phys.Chem.B,2004,108(48):18772-18778.
[17]LINDSEY A S.The structure of cyclotriveratrylene and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[18]CERRINI S,GIGLIO E,MAZZA F,PAVEL N V.The crystal structure of the inclusion compound between cycloveratril,benzene and water[J].Acta.Cryst.,1979,B35:2605-2609.
[19]HYATT J A,DUESLER E N,CURTIN D Y,PAUL I C.Stoichiometric inclusion compounds of cyclotriveratrylene and cyclotricatechylene with small neutral molecules.X-ray crystal structure of cyclotricatechylene di-2-propanolate[J].J.Org.Chem.,1980,45(25):5074-5079.
[20]COLLET A,GABARD J,JACQUES J,CESARIO M,GUILHERN J,PASCARD C.Synthesis and absolute configuration of chiral(C3) cyclotriveratrylene.Crystal structure of(M)-(-)-2,7,12-triethoxy-3,8,13-tris-[(R)-1-methoxycarbonyl ethoxy]-10,15-ihydro-5H-tribenzo[a,d,g]-cyclononene[J].J.Chem.Soc.,Perkin Trans.1981,1:1630-1638.
[21]LEHN J M.Comprehensive supramolecular chemistry.Oxford:Pergamon,1996,2:325-340.
[22]ZHANG S,PALKAR A,FRAGOSO A,PRADOS P,MENDOZA J,ECHEGOYEN L.Noncovalent immobilization of C60 on gold surfaces by SAMs of cyclotriveratrylene derivatives[J].Chem.Mater,2005,17:2063-2068.
[23]STEED J W,ATWOD J L.Supramoleeular Chemistry.Chichester:Wiley,2000,205-208.
[24]SATO T,UNO K.Medium-sized cyclophanes.Part ⅩⅤ.10,15-Dihydro-5H-tribenzo-[a,d,g]cyclononene and analogues[J].J.Chem.Soc.,Perkin Trans.,1973,1:895-900.
[25]STEED J W,ZHANG H,ATWOOD J L.Inclusion chemistry of cyclotriveratrylene and cyclotricatechylene.Supramol.Chem.,1996,7(1):37-45.
[26]AHMAD R,HARDIE M J.Synthesis and structural studies of cyclotriveratrylene derivatives.Supramol.Chem.,2006,18(1):29-38.
[27]BURLINSON N E,RIPMEESTER J A.Characterization of cyclotriveratrylene inclusion compounds by means of solid state ~(13)CNMR[J].J.Incl.Phenomena.,1984,1(4):403-409.
[28]COLLET A.Cyclotriveratrylenes and cryptophanes[J].Tetrahedron,1987,43(24):5725-5744.
[29]FRENSCH K,VOGTLE F.Notiz fiber oigoethylenglykolether des morphins[J].Liebigs.Ann.Chem.,1979,12:2118-2120.
[30]MENGER F,TAKESHITA M,CHOW J F.Hexapus,a new complexing agent for organic molecules[J].J.Am.Chem.Soc.,1981,103(19):5938-5939.
[31]BERGMAN J,HOBERG S,LINDSTROM J O.Macrocyclic condensation products of indole and simple aldehydes[J].Tetrahedron,1970,26(13):3347-3352.
[32]TREIBS A,KREUZER F H,HABERLE N.Tripyrryl-trismethane(Hexahydro-cyclononatripyrrole)[J].Liebigs Ann.Chem.,1970,733(1):37-43.
[33]METH C.Novel macrocycles from 2,5-dimethylthiophen and related systems[J].Tetrahedron Lett.,1973,14(2):91-94.
[34]LINDSEY A S.The structure of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy -5H-tribenzo[a,d,g]cyclononene) and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[35]SATO T,AKIMA T,UNO K.Medium-sized cyclophanes.Part ⅪⅤ.An aromatic displacement reaction in veratrylic compounds.Attempted nitration and halogenation of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy-5H-tri-benzo[a,d,g]cyclononene)[J].J.Gem.Soc.,Perkin Trans.,1973,1:891-895.
[36]SATO T,UNO K,KAINOSHO M.A new synthesis of bridged aromatics:10,15-dihydro -5H-tribenzo[a,d,g]cyclononene and its analogues[J].J.Chem.Soc.,Chem.Commun.,1972,579-580.
[37]SATO T,UNO K.Medium-sized cyclophanes.Part ⅩⅤ.10,15-Dihydro-5H-tribenzo[a,d,g]cyclononene and analogues[J].J.Chem.Soc.,Perkin Trans.,1973,1:895-900.
[38] AHMAD R, DIX I, HARDIE M J. Hydrogen-bonded superstructures of a small host molecule and lanthanide aquo ions[J]. Inorg. Chem., 2003, 42(7): 2182-2184.
[39] TRAVISHOLMAN K, WILLIAMORR G, ATWOOD J L, STEED J W. Deep cavity [CpFe(arene)]~+ derivatized cyclotriveratrylenes as anion hosts [J]. Chem. Commun., 1998,2109-2110.
[40] KONAREV D V, KHASANOV S S, VORONTSOV I I, SAITO G, ANTIPIN M Y, OTSUKA A, LYUBOVSKAYA R N. The formation of a single-bonded (C_(70)-)_2 dimer in a new ionic multicomponent complex of cyclotriveratrylene: (Cs~+)_2 (C~(70)~-)_2·CTV·(DMF)_7(C_6H_6)_(0.75)[J]. Chem. Commun., 2002, 2548-2549.
[41] ZHANG S, ECHEGOYEN L. Supramolecular immobilization of fullerenes on gold surfaces: receptors based on calix[n]arenes, cyclotriveratrylene (CTV) and porphyrins [J]. Comptes Rendus Chim. 2006, 9(7-8): 1031-1037
[42] HERBERT Z, VICTORIA B, RAHPY P. Mesomorphism, i-somerization, and dynamics in a new series of pyramidic liquid crystals[J]. J Am Chem Soc, 2002, 124(51): 15286-15301.
[43] ZIMMERMANN H, TOLSTOY P, LIMBACH H H, POUPKO R, LUZ Z. The saddle form of cyclotriveratrylene[J]. J. Phys. Chem. B., 2004, 108(48): 18772.
[44] JASAT A, SHERMAN J C. Carceplexes and hemicarceplexes[J]. Chem. Rev., 1999, 99(4): 931-968.
[45] KATHLEEN E C, MALGORZATA M, GOODSON B M. ~1HNMR studies of chloroform-cryptophane-A and chloroform bis-cryptophane inclusion complexes oriented in thermotropic liquid crystals[J]. Solid State Nuclear Magnetic Rcsonance, 2006,29(1-3): 104-112.
[46] BARTIK K, LUHMER M, COLLET A, et al. ~(129)Xe and ~1H NMR Study of the Reversible Trapping of Xenon by Cryptophane-A in Organic Solution[J]. J. Am. Chem. Soc, 1998, 120(4): 784-791.
[47] CANCEILL J, LACOMBE L, COLLET A. Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made cryptophane and determination of its maximum rotation[J]. J. Am. Chem. Soc, 1985, 107(24): 6993-6996.
[48] COLLET A. Cyclotriveratrylenes and cryptophanes[J]. Tetrahedron, 1987, 43(24): 5725-5744.
[49]CANCEII J,COLLET A.Two-step synthesis of D_3 and C_(3h) cryptophanes[J].J.Chem.Soc.,Chem.Commun.,1988,9:582-584.
[50]Mough S T,Goeltz J C,Holman K T.Isolation and Structure of an "Imploded"Cryptophane[J].Angew.Chem.,2004,43(42):5631-5635.
[51]BROTIN T,ROY V,DUTASTA J R Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)_3 as Catalyst[J].Jr.Org.Chem.2005,70(16):6187-6195.
[52]HUBER G,BROTIN T,DUBOIS L,DESVAUX H,DUTASTA J P,BERTHAULT P.Water Soluble Cryptophanes Showing Unprecedented Affinity for Xenon Candidates as NMR-Based Biosensors[J].J.Am.Chem.Soc.,2006,128(18):6239-6246.
[53]COLLET A.Cyclotriveratrylenes and Cryptophanes[J].Tetrahedron,1987,43(24):5745-5759.
[54]GAREL L,DUTASTA J P,COLLET A.Complexation of Methane and Chlorofluorocarbons by Cryptophane-A in Organic Solution[J].Angew.Chem.Int.Ed.Engl.,1993,32(8):1169-1171.
[55]EMANUELA L,MARIANO C,KRISTIN B.The Potential of ~(129)Xe NMR Relaxation Measurements for the Study of Heine Proteins[J].ChemPhysChem,2002,3(9):812-814.
[56]BROTIN T,DEVIC T,LESAGE A,EMSLEY L,COLLET A.Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe-Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments[J].Chem.eur.J.,2001,7(7):1561-1573.
[57]GOODSON B M.Nuclear Magnetic Resonance of Laser-Polarized Noble Gases in Molecules,Materials,and Organisms[J].J.Magn.Reson.,2002,155(2):157-216.
[58]CHERUBINI A,BIFONE A.Hyperpolarised xenon in biology[J].Prog.Nucl.Magn.Reson.Spectrosc.,2003,42:1-30.
[59]OROS A M,SHAH N.Hyperpolarized xenon in NMR and MRI[J].J.Phys.Med.Biol.,2004,49(20-21):105-153.
[60]BARTIK K,CHOQUET P,CONSTANTINESCO A,DUHAMEL G,FRAISSARD K L.Self-Assembly of a 3-D Triply Interlocked Chiral[2]Catenane[J].J.Am.Chem.Soc.,2008,130(10):2950-2951.
[61] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, PASCARD C. A new bis-cyclotribenzyl cavitand capable of selective inclusion of neutral molecules in solution. Crystal structure of its CH_2Cl_2 cavitate[J]., J. Chem. Soc, Chem. Commun., 1985,361-363.
[62] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, PASCARD C. Selective recognition of neutral molecules: ~1HNMR Study of the complexation of CH_2Cl_2 and CH_2Br_2 by cryptophane-D in solution and crystal structure of its CH_2Cl_2 cavitate[J]. J. Chem. Soc, Chem. Commun., 1986, 339-341.
[63] CANCEILL J, LACOMBE L, COLLET A. Analytical Optical Resolution Of Bromocholorofluoromethane by Enantioselective Inclusion into aTailor-Made cryptophane and Determination of Its Maximum Rotation[J]. J. Am. Chem. Soc, 1985,107: 6993-6996.
[64] BARTIK K, LUHMER M, DUTASTA J P, COLLE A, REISSE J. ~(129)Xe and ~1HNMR study of the reversible trapping of xenon by cryptophane-A in organic solution[J]. J. Am. Chem. Soc, 1998, 120(4): 784.
[65] GARCIA C, AUBRY A, COLLET A. Bull. Soc. Chim. Fr. 1996, 133: 853-867.
[66] GARCIA C, HUMILIE'RE D, RIVA N, COLLET A, DUTASTA J P. Kinetic and thermodynamic consequences of the substitution of SMe for OMe substituents of cryptophane hosts on the binding of neutral and cationic guests[J]. Org. Biomol. Chem., 2003,1(12): 2207-2216.
[1]LINDSEY A S.The structure of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy -5H-tribenzo[a,d,g]cyclononene) and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[2]JOSETTE C,ANDRE C,JACQUELINE G,et al.Exciton approach to the optical activity of C3-cyclotrylene derivatives[J].J.Am.Chem.Soc.,1985,107:1299-1308.
[3]ANDRE C,JACQUELINE G.Optically active(C_3)-cyclotriveratrylene-d9 energy barrier for the "crown to crown" conformational interconversion of its nine-membered-ring system[J].J Org Chem.,1980,45:5400-5401.
[4]JEANNE C,CHANTAL G,ANDRE C.Key intermediates in cyclotriveratrylene chemistry:a new route to the enantiomersof C_3-cyclotriphenolene and cryptophane-c[J].Chirality,1997,9:446-453.
[5]COLLET A.Cyclotriveratrylenes and cryptophanes[J].Tetrahedron,1987,43(24):5725-5759.
[6]WHITE J D,GESNER B D.Cyclotetraveratrylene,a conformationally mobile structure.Tetrahedron Lett.,1968,9(13):1591-1594.
[7]SAKURAI H,ERIYAMA Y,HOSOMI A,NAKADAIRA Y,KABUTO C.Peparation and reactions of dodecamethyl-3,4,7,8,11,12-hexasilacyclododeca-1,5,9-triyne[J].Chem.Lett.,1984,13(4):595-598.
[8] GARCHIA C, ANDRAUD C, COLLET A. New key compounds in cyclotriveratrylene chemistry. Synthesis, optical resolution, absolute configuration and circular dichroism of C3- cyclotriveratrylenes with sulfur substituents[J]. Supramol. Chem., 1992, 1(1): 31-45.
[9] TREIBS A, KREUZER F H, HABERLE N. Tripyrryl-trismethane (Hexahydro- cyclonona tripyrrole)[J]. Liebigs Ann. Chem., 1970, 733(1): 37-43.
[10] DELPINE F, BENOIT H, DANIEL G, et al. A liquid crystalline supramolecular complex of C60 with a cyclotriveratrylene derivative [J]. Chem Eur J, 2000, 6: 3501-3507.
[11] GILLES V, JEAN-PIERRE D, GALINA M, et al. Synthesis of C_3-Cyclotriveratrylene ligands for iron(Ⅱ) and iron(Ⅲ) coordination[J]. Tetrehedron, 1995, 51(2): 389-400.
[12] MENGER F, TAKESHITA M, CHOW J F. Hexapus, a new complexing agent for organic molecules[J]. J. Am. Chem. Soc, 1981,103(19): 5938-5939.
[1]GAREL B,LAURENT Y,DUTASTA P D,COLLET A.Complexation of Methane and Chlorofluorocarbons by Cryptophane-A in Organic Solution[J].Angew.Chem.Int.Ed.Engl.,1993,32:1169-1171.
[2]IZATT R M,BRADSHAW J S,PAWLAK K,et al.Thermodynamic and Kinetic Data for Macrocycle Interaction with Neutral Molecular[J].Chem.Rev,1992,92:261-1354.
[3]BARTIK K,LUHMER M,COLLET A,et al.~(129)Xe and ~1HNMR Study of the Reversible Trapping of Xenon by Cryptophane-A in Organic Solution[J].J.Am.Chem.Soc,1998,120:784-791.
[4]Laurent Garel,Benedicte Lozach,Jean-pierre Dutasta,Andre Collet.,Remarkable Effect of Receptor Size in the Binding of Acetylcholine and Related Ammonium Ions to Water-soluble Cryptophane[J].J.Am.Chem.Soc.,1993,115:11652-11653.
[5]Fogarty H A,Berthault P,Brotin T,Huber G,Desvaux H,Dutasta J P.A Cryptophane Core Optimized for Xenon Encapsulation[J].J.Am.Chem.Soc.,2007,129(34):10332-10333.
[6]CHAFFEE K E,MARJANSKA M,GOODSON B M.~1HNMR studies of chloroform-cryptophane-A and chloroform-bis-cryptophane inclusion complexes oriented in thermotropic liquid crystals[J].Solid.State.Nuclear.Magnetic.Rcsonance,2006,29:104-112.
[7]CANCEILI J,CESARIO M,COLLI ET ANDRE,et al.Structure and Properties of the Cryptophane-E CHCl_3 Complex a Stable van der Waals Molecule[J].Angew.Chem.Int.Ed.Engl.,1989,28:1246-1248.
[8]COLLET A.Cyclotriveratrylenes and Cryptophanes[J].Tetrahedron,1987,43(24):5745-5759.
[9]CANCEII J,COLLET A.Two-step synthesis of D_3 and C_(3h) cryptophanes[J].J.Chem.Soc.Chem.Cornmun,1988,9:582-584.
[10]CANCEILL J,LACOMBE L,COLLET A.New Cryptophane Forming Unusally Stable Inclusion Complexes With Neutral Guests in a Linpophilic Solvent[J].J.Am.Chem.Soc.,1986,108:4230-4232.
[1]CRAM D J.Preorganisation-from solvent to spherands[J].Angew Chem.Int.Ed.Engl.,1986,25:1039-1057.
[2]J.W.斯蒂德,J.L.阿特伍德.超分子化学,化学工业出版社,2006,175-180
[3]FOGARTY H A,BERTHAULT P,BROTIN T,HUBER G,DESVAUX H,DUTASTA J P.A Cryptophane Core Optimized for Xenon Encapsulation[J].J.Am.Chem.Soc.,2007,129(34):10332-10333.
[4]KIM E I,PALIWAL,WILCOX C S.Measurments of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition[J].J.Am.Chem.Soc,1998,120:11192-11193.
[5]CANCEILL J,LACOMBE L,COLLET A.Water-soluble cryptophane binding lipophilic guests in aqueous solution[J].J.Chem.Soc.,Chem.Commun.,1987,3:219-221.
[6]CANCEILL J,LACOMBE L,COLLET A.New cryptophane forming unusually stable inclusion complexes with neutral guests in a lipophilic solvent[J].J.Am.Chem.Soc.,1986,108:4230-4232.
[7] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, LACOMBE L, LOZACH B, PASCARD C. Structure and Properties of the Cryptophane-E/CHCl_3 Complex, a Stable van der Waals Molecule[J]. Angew Chem. Int. Ed. Engl, 1989, 28 (9): 1246-1248.
[8] CAVAGNAT D, BROTIN T, BRUNEEL J, DUTASTA J, THOZET A, PERRIN M, GUILLAUME F. Raman Microspectrometry as a New Approach to the Investigation of Molecular Recognition in Solids: Chloroform-Cryptophane Complexes[J]. J. Phys. Chem. B, 2004,108(18): 5572-5581.
[9] P E GEORGHIOU, TRAN A H, STROUD S S, THOMPSON D W. Supramolecular complexation studies of [60]fullerene with calix[4]naphthalenes-a reinvestigation[J]. Tetrahedron, 2006, 62 (9): 2036-2044.
[10] CATENA G C, BRIGHT F V. The Thermodynamic Study on the Effects of eta-cyclodextrin Inclusion with Anilino-Naphthyl Sulfonates[J]. Anal. Chem. 1989, 61: 905-909.
[11] LIU Y, HAN B H, CHEN Y T. Molecular Recognition and Complexation Thermodynamics of Dye Guest Molecules by Modified Cyclodextrins and Calixarenesulfonates[J]. J. Phys. Chem. B, 2002, 106: 4678-4687.
[12] INOUE Y, YAMAMOTO K, WADA T, EVERITT S. Inclusion complexation of (cyclo)alkanes and (cyclo)alkanols with 6-O-modified cyclodextrins[J]. J.Chem. Soc, Perkin Trans.2, 1998, 8: 1807.
[13] PANG Y H, YANG L L, SHUANG S M, DONG C, THOMPSON M. Interaction of human serum albumin with bendroflumethiazide studied by fluorescence spectroscopy[J]. J. Photochem. Photobiol. B, 2005, 80(2): 139-144.
[14] POWELL H M. The structure of molecular compounds. Part IV. Clathrate compounds[J]. J. Chem. Soc, 1948, 61-73.
[15] COLLET A, DUTASTA J P, LOZACH B. Design, synthesis and properties of macrocyclic receptors for tetrahedral substrates[J]. Bull. Soc. Chim. Bel, 1990, 99: 617-633.
[2]CRAM D.The design of molecular hosts,guests,and their complexes[J].Angew Chem.Int.Ed.Engl.,1988,27(8):1009-1020.
[3]LEHN J M.Supramolecular chemistry-scope and perspectives molecules,supermolecules,and molecular devices[J].Angew.Chem.,Int.Ed.Engl.,1988,27(1):89-112.
[4]DOMINIK A,ROTH H J,SCHIERBAUM K D,GOPEL W.Supramolecular complexes based on calixarenes:force field calculations and applications for chemical sensors[J].Supramolecular Science,1994,1:11-19.
[5]SCHNEIDER H J,YATSIMIRSKY A.Principles and methods in supramolecular Chemistry.Chichester:Wiley,1999,225-230.
[6]OSHITA K,TAKAYANAGI T,OSHIMA M,MOTOMIZU S.Complex formation analysis of water-soluble calixarenes by capillary zone electrophoresis[J].Journal of Chromatography A,2001,934:113-122.
[7]LEHN J M.Comprehensive supramolecular chemistry.Oxford:Pergamon,1996,1:30-34.
[8]沈家骢,孙俊奇.超分子科学研究进展[J].中国科学院院刊,2004,19:420-424.
[9]NIDAN G,NIEL M-A.Electride modified by sulfonated calixarenes immobilized into a polypyrrole filem:a step towards new ion-sensitive layer[J].Synthetic metal,1997,84:225-256.
[10]ZHONG Z L,CHEN Y Y,LU X R.Calix[4]arenas and double calix[4]arenes bridged via calixarenes segments[J].Tetrahedron Letters,1995,36:6735-6738.
[11]MNUK P,FELEL L,SCHURIG V.Gas chromatographic study of the inclusion properties of calixarenes[J].Journal of Chromatography,1996,732:63-74.
[12]Robinson G M.A reaction of homopiperonyl and of homoveratryl alcohols[J].J.Chem.Soc.,Trans.,1915,107:267-276.
[13]EWINS A J.The action of phosphorus pentachloride on the methylene ethers of catechol.Part Ⅴ.of protocatechuyl alcohol and protocatechuonitrile[J].J.Chem. Soc.,Trans.,1909,95:1482-1488.
[14]White J D,Gesner B D.Cyclotetraveratrylene,a conformationally mobile structure[J].Tetrahedron Lett.,1968,9(13):1591-1594.
[15]ERDTMAN H,HAGLID F,RYHAGE R.Macrocyclic condensation products of veratrole and resorcinol[J].Acta.Chem.Scand.,1964,18:1249-1254.
[16]ZIMMERMANN H,TOLSTOY P,LIMBACH H,POUPKO R,LUZ Z.The saddle form of cyclotriveratrylene[J].J.Phys.Chem.B,2004,108(48):18772-18778.
[17]LINDSEY A S.The structure of cyclotriveratrylene and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[18]CERRINI S,GIGLIO E,MAZZA F,PAVEL N V.The crystal structure of the inclusion compound between cycloveratril,benzene and water[J].Acta.Cryst.,1979,B35:2605-2609.
[19]HYATT J A,DUESLER E N,CURTIN D Y,PAUL I C.Stoichiometric inclusion compounds of cyclotriveratrylene and cyclotricatechylene with small neutral molecules.X-ray crystal structure of cyclotricatechylene di-2-propanolate[J].J.Org.Chem.,1980,45(25):5074-5079.
[20]COLLET A,GABARD J,JACQUES J,CESARIO M,GUILHERN J,PASCARD C.Synthesis and absolute configuration of chiral(C3) cyclotriveratrylene.Crystal structure of(M)-(-)-2,7,12-triethoxy-3,8,13-tris-[(R)-1-methoxycarbonyl ethoxy]-10,15-ihydro-5H-tribenzo[a,d,g]-cyclononene[J].J.Chem.Soc.,Perkin Trans.1981,1:1630-1638.
[21]LEHN J M.Comprehensive supramolecular chemistry.Oxford:Pergamon,1996,2:325-340.
[22]ZHANG S,PALKAR A,FRAGOSO A,PRADOS P,MENDOZA J,ECHEGOYEN L.Noncovalent immobilization of C60 on gold surfaces by SAMs of cyclotriveratrylene derivatives[J].Chem.Mater,2005,17:2063-2068.
[23]STEED J W,ATWOD J L.Supramoleeular Chemistry.Chichester:Wiley,2000,205-208.
[24]SATO T,UNO K.Medium-sized cyclophanes.Part ⅩⅤ.10,15-Dihydro-5H-tribenzo-[a,d,g]cyclononene and analogues[J].J.Chem.Soc.,Perkin Trans.,1973,1:895-900.
[25]STEED J W,ZHANG H,ATWOOD J L.Inclusion chemistry of cyclotriveratrylene and cyclotricatechylene.Supramol.Chem.,1996,7(1):37-45.
[26]AHMAD R,HARDIE M J.Synthesis and structural studies of cyclotriveratrylene derivatives.Supramol.Chem.,2006,18(1):29-38.
[27]BURLINSON N E,RIPMEESTER J A.Characterization of cyclotriveratrylene inclusion compounds by means of solid state ~(13)CNMR[J].J.Incl.Phenomena.,1984,1(4):403-409.
[28]COLLET A.Cyclotriveratrylenes and cryptophanes[J].Tetrahedron,1987,43(24):5725-5744.
[29]FRENSCH K,VOGTLE F.Notiz fiber oigoethylenglykolether des morphins[J].Liebigs.Ann.Chem.,1979,12:2118-2120.
[30]MENGER F,TAKESHITA M,CHOW J F.Hexapus,a new complexing agent for organic molecules[J].J.Am.Chem.Soc.,1981,103(19):5938-5939.
[31]BERGMAN J,HOBERG S,LINDSTROM J O.Macrocyclic condensation products of indole and simple aldehydes[J].Tetrahedron,1970,26(13):3347-3352.
[32]TREIBS A,KREUZER F H,HABERLE N.Tripyrryl-trismethane(Hexahydro-cyclononatripyrrole)[J].Liebigs Ann.Chem.,1970,733(1):37-43.
[33]METH C.Novel macrocycles from 2,5-dimethylthiophen and related systems[J].Tetrahedron Lett.,1973,14(2):91-94.
[34]LINDSEY A S.The structure of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy -5H-tribenzo[a,d,g]cyclononene) and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[35]SATO T,AKIMA T,UNO K.Medium-sized cyclophanes.Part ⅪⅤ.An aromatic displacement reaction in veratrylic compounds.Attempted nitration and halogenation of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy-5H-tri-benzo[a,d,g]cyclononene)[J].J.Gem.Soc.,Perkin Trans.,1973,1:891-895.
[36]SATO T,UNO K,KAINOSHO M.A new synthesis of bridged aromatics:10,15-dihydro -5H-tribenzo[a,d,g]cyclononene and its analogues[J].J.Chem.Soc.,Chem.Commun.,1972,579-580.
[37]SATO T,UNO K.Medium-sized cyclophanes.Part ⅩⅤ.10,15-Dihydro-5H-tribenzo[a,d,g]cyclononene and analogues[J].J.Chem.Soc.,Perkin Trans.,1973,1:895-900.
[38] AHMAD R, DIX I, HARDIE M J. Hydrogen-bonded superstructures of a small host molecule and lanthanide aquo ions[J]. Inorg. Chem., 2003, 42(7): 2182-2184.
[39] TRAVISHOLMAN K, WILLIAMORR G, ATWOOD J L, STEED J W. Deep cavity [CpFe(arene)]~+ derivatized cyclotriveratrylenes as anion hosts [J]. Chem. Commun., 1998,2109-2110.
[40] KONAREV D V, KHASANOV S S, VORONTSOV I I, SAITO G, ANTIPIN M Y, OTSUKA A, LYUBOVSKAYA R N. The formation of a single-bonded (C_(70)-)_2 dimer in a new ionic multicomponent complex of cyclotriveratrylene: (Cs~+)_2 (C~(70)~-)_2·CTV·(DMF)_7(C_6H_6)_(0.75)[J]. Chem. Commun., 2002, 2548-2549.
[41] ZHANG S, ECHEGOYEN L. Supramolecular immobilization of fullerenes on gold surfaces: receptors based on calix[n]arenes, cyclotriveratrylene (CTV) and porphyrins [J]. Comptes Rendus Chim. 2006, 9(7-8): 1031-1037
[42] HERBERT Z, VICTORIA B, RAHPY P. Mesomorphism, i-somerization, and dynamics in a new series of pyramidic liquid crystals[J]. J Am Chem Soc, 2002, 124(51): 15286-15301.
[43] ZIMMERMANN H, TOLSTOY P, LIMBACH H H, POUPKO R, LUZ Z. The saddle form of cyclotriveratrylene[J]. J. Phys. Chem. B., 2004, 108(48): 18772.
[44] JASAT A, SHERMAN J C. Carceplexes and hemicarceplexes[J]. Chem. Rev., 1999, 99(4): 931-968.
[45] KATHLEEN E C, MALGORZATA M, GOODSON B M. ~1HNMR studies of chloroform-cryptophane-A and chloroform bis-cryptophane inclusion complexes oriented in thermotropic liquid crystals[J]. Solid State Nuclear Magnetic Rcsonance, 2006,29(1-3): 104-112.
[46] BARTIK K, LUHMER M, COLLET A, et al. ~(129)Xe and ~1H NMR Study of the Reversible Trapping of Xenon by Cryptophane-A in Organic Solution[J]. J. Am. Chem. Soc, 1998, 120(4): 784-791.
[47] CANCEILL J, LACOMBE L, COLLET A. Analytical optical resolution of bromochlorofluoromethane by enantioselective inclusion into a tailor-made cryptophane and determination of its maximum rotation[J]. J. Am. Chem. Soc, 1985, 107(24): 6993-6996.
[48] COLLET A. Cyclotriveratrylenes and cryptophanes[J]. Tetrahedron, 1987, 43(24): 5725-5744.
[49]CANCEII J,COLLET A.Two-step synthesis of D_3 and C_(3h) cryptophanes[J].J.Chem.Soc.,Chem.Commun.,1988,9:582-584.
[50]Mough S T,Goeltz J C,Holman K T.Isolation and Structure of an "Imploded"Cryptophane[J].Angew.Chem.,2004,43(42):5631-5635.
[51]BROTIN T,ROY V,DUTASTA J R Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)_3 as Catalyst[J].Jr.Org.Chem.2005,70(16):6187-6195.
[52]HUBER G,BROTIN T,DUBOIS L,DESVAUX H,DUTASTA J P,BERTHAULT P.Water Soluble Cryptophanes Showing Unprecedented Affinity for Xenon Candidates as NMR-Based Biosensors[J].J.Am.Chem.Soc.,2006,128(18):6239-6246.
[53]COLLET A.Cyclotriveratrylenes and Cryptophanes[J].Tetrahedron,1987,43(24):5745-5759.
[54]GAREL L,DUTASTA J P,COLLET A.Complexation of Methane and Chlorofluorocarbons by Cryptophane-A in Organic Solution[J].Angew.Chem.Int.Ed.Engl.,1993,32(8):1169-1171.
[55]EMANUELA L,MARIANO C,KRISTIN B.The Potential of ~(129)Xe NMR Relaxation Measurements for the Study of Heine Proteins[J].ChemPhysChem,2002,3(9):812-814.
[56]BROTIN T,DEVIC T,LESAGE A,EMSLEY L,COLLET A.Synthesis of Deuterium-Labeled Cryptophane-A and Investigation of Xe-Cryptophane Complexation Dynamics by 1D-EXSY NMR Experiments[J].Chem.eur.J.,2001,7(7):1561-1573.
[57]GOODSON B M.Nuclear Magnetic Resonance of Laser-Polarized Noble Gases in Molecules,Materials,and Organisms[J].J.Magn.Reson.,2002,155(2):157-216.
[58]CHERUBINI A,BIFONE A.Hyperpolarised xenon in biology[J].Prog.Nucl.Magn.Reson.Spectrosc.,2003,42:1-30.
[59]OROS A M,SHAH N.Hyperpolarized xenon in NMR and MRI[J].J.Phys.Med.Biol.,2004,49(20-21):105-153.
[60]BARTIK K,CHOQUET P,CONSTANTINESCO A,DUHAMEL G,FRAISSARD K L.Self-Assembly of a 3-D Triply Interlocked Chiral[2]Catenane[J].J.Am.Chem.Soc.,2008,130(10):2950-2951.
[61] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, PASCARD C. A new bis-cyclotribenzyl cavitand capable of selective inclusion of neutral molecules in solution. Crystal structure of its CH_2Cl_2 cavitate[J]., J. Chem. Soc, Chem. Commun., 1985,361-363.
[62] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, PASCARD C. Selective recognition of neutral molecules: ~1HNMR Study of the complexation of CH_2Cl_2 and CH_2Br_2 by cryptophane-D in solution and crystal structure of its CH_2Cl_2 cavitate[J]. J. Chem. Soc, Chem. Commun., 1986, 339-341.
[63] CANCEILL J, LACOMBE L, COLLET A. Analytical Optical Resolution Of Bromocholorofluoromethane by Enantioselective Inclusion into aTailor-Made cryptophane and Determination of Its Maximum Rotation[J]. J. Am. Chem. Soc, 1985,107: 6993-6996.
[64] BARTIK K, LUHMER M, DUTASTA J P, COLLE A, REISSE J. ~(129)Xe and ~1HNMR study of the reversible trapping of xenon by cryptophane-A in organic solution[J]. J. Am. Chem. Soc, 1998, 120(4): 784.
[65] GARCIA C, AUBRY A, COLLET A. Bull. Soc. Chim. Fr. 1996, 133: 853-867.
[66] GARCIA C, HUMILIE'RE D, RIVA N, COLLET A, DUTASTA J P. Kinetic and thermodynamic consequences of the substitution of SMe for OMe substituents of cryptophane hosts on the binding of neutral and cationic guests[J]. Org. Biomol. Chem., 2003,1(12): 2207-2216.
[1]LINDSEY A S.The structure of cyclotriveratrylene(10,15-dihydro-2,3,7,8,12,13-hexamethoxy -5H-tribenzo[a,d,g]cyclononene) and related compounds[J].J.Chem.Soc.,1965,1685-1692.
[2]JOSETTE C,ANDRE C,JACQUELINE G,et al.Exciton approach to the optical activity of C3-cyclotrylene derivatives[J].J.Am.Chem.Soc.,1985,107:1299-1308.
[3]ANDRE C,JACQUELINE G.Optically active(C_3)-cyclotriveratrylene-d9 energy barrier for the "crown to crown" conformational interconversion of its nine-membered-ring system[J].J Org Chem.,1980,45:5400-5401.
[4]JEANNE C,CHANTAL G,ANDRE C.Key intermediates in cyclotriveratrylene chemistry:a new route to the enantiomersof C_3-cyclotriphenolene and cryptophane-c[J].Chirality,1997,9:446-453.
[5]COLLET A.Cyclotriveratrylenes and cryptophanes[J].Tetrahedron,1987,43(24):5725-5759.
[6]WHITE J D,GESNER B D.Cyclotetraveratrylene,a conformationally mobile structure.Tetrahedron Lett.,1968,9(13):1591-1594.
[7]SAKURAI H,ERIYAMA Y,HOSOMI A,NAKADAIRA Y,KABUTO C.Peparation and reactions of dodecamethyl-3,4,7,8,11,12-hexasilacyclododeca-1,5,9-triyne[J].Chem.Lett.,1984,13(4):595-598.
[8] GARCHIA C, ANDRAUD C, COLLET A. New key compounds in cyclotriveratrylene chemistry. Synthesis, optical resolution, absolute configuration and circular dichroism of C3- cyclotriveratrylenes with sulfur substituents[J]. Supramol. Chem., 1992, 1(1): 31-45.
[9] TREIBS A, KREUZER F H, HABERLE N. Tripyrryl-trismethane (Hexahydro- cyclonona tripyrrole)[J]. Liebigs Ann. Chem., 1970, 733(1): 37-43.
[10] DELPINE F, BENOIT H, DANIEL G, et al. A liquid crystalline supramolecular complex of C60 with a cyclotriveratrylene derivative [J]. Chem Eur J, 2000, 6: 3501-3507.
[11] GILLES V, JEAN-PIERRE D, GALINA M, et al. Synthesis of C_3-Cyclotriveratrylene ligands for iron(Ⅱ) and iron(Ⅲ) coordination[J]. Tetrehedron, 1995, 51(2): 389-400.
[12] MENGER F, TAKESHITA M, CHOW J F. Hexapus, a new complexing agent for organic molecules[J]. J. Am. Chem. Soc, 1981,103(19): 5938-5939.
[1]GAREL B,LAURENT Y,DUTASTA P D,COLLET A.Complexation of Methane and Chlorofluorocarbons by Cryptophane-A in Organic Solution[J].Angew.Chem.Int.Ed.Engl.,1993,32:1169-1171.
[2]IZATT R M,BRADSHAW J S,PAWLAK K,et al.Thermodynamic and Kinetic Data for Macrocycle Interaction with Neutral Molecular[J].Chem.Rev,1992,92:261-1354.
[3]BARTIK K,LUHMER M,COLLET A,et al.~(129)Xe and ~1HNMR Study of the Reversible Trapping of Xenon by Cryptophane-A in Organic Solution[J].J.Am.Chem.Soc,1998,120:784-791.
[4]Laurent Garel,Benedicte Lozach,Jean-pierre Dutasta,Andre Collet.,Remarkable Effect of Receptor Size in the Binding of Acetylcholine and Related Ammonium Ions to Water-soluble Cryptophane[J].J.Am.Chem.Soc.,1993,115:11652-11653.
[5]Fogarty H A,Berthault P,Brotin T,Huber G,Desvaux H,Dutasta J P.A Cryptophane Core Optimized for Xenon Encapsulation[J].J.Am.Chem.Soc.,2007,129(34):10332-10333.
[6]CHAFFEE K E,MARJANSKA M,GOODSON B M.~1HNMR studies of chloroform-cryptophane-A and chloroform-bis-cryptophane inclusion complexes oriented in thermotropic liquid crystals[J].Solid.State.Nuclear.Magnetic.Rcsonance,2006,29:104-112.
[7]CANCEILI J,CESARIO M,COLLI ET ANDRE,et al.Structure and Properties of the Cryptophane-E CHCl_3 Complex a Stable van der Waals Molecule[J].Angew.Chem.Int.Ed.Engl.,1989,28:1246-1248.
[8]COLLET A.Cyclotriveratrylenes and Cryptophanes[J].Tetrahedron,1987,43(24):5745-5759.
[9]CANCEII J,COLLET A.Two-step synthesis of D_3 and C_(3h) cryptophanes[J].J.Chem.Soc.Chem.Cornmun,1988,9:582-584.
[10]CANCEILL J,LACOMBE L,COLLET A.New Cryptophane Forming Unusally Stable Inclusion Complexes With Neutral Guests in a Linpophilic Solvent[J].J.Am.Chem.Soc.,1986,108:4230-4232.
[1]CRAM D J.Preorganisation-from solvent to spherands[J].Angew Chem.Int.Ed.Engl.,1986,25:1039-1057.
[2]J.W.斯蒂德,J.L.阿特伍德.超分子化学,化学工业出版社,2006,175-180
[3]FOGARTY H A,BERTHAULT P,BROTIN T,HUBER G,DESVAUX H,DUTASTA J P.A Cryptophane Core Optimized for Xenon Encapsulation[J].J.Am.Chem.Soc.,2007,129(34):10332-10333.
[4]KIM E I,PALIWAL,WILCOX C S.Measurments of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition[J].J.Am.Chem.Soc,1998,120:11192-11193.
[5]CANCEILL J,LACOMBE L,COLLET A.Water-soluble cryptophane binding lipophilic guests in aqueous solution[J].J.Chem.Soc.,Chem.Commun.,1987,3:219-221.
[6]CANCEILL J,LACOMBE L,COLLET A.New cryptophane forming unusually stable inclusion complexes with neutral guests in a lipophilic solvent[J].J.Am.Chem.Soc.,1986,108:4230-4232.
[7] CANCEILL J, CESARIO M, COLLET A, GUILHEM J, LACOMBE L, LOZACH B, PASCARD C. Structure and Properties of the Cryptophane-E/CHCl_3 Complex, a Stable van der Waals Molecule[J]. Angew Chem. Int. Ed. Engl, 1989, 28 (9): 1246-1248.
[8] CAVAGNAT D, BROTIN T, BRUNEEL J, DUTASTA J, THOZET A, PERRIN M, GUILLAUME F. Raman Microspectrometry as a New Approach to the Investigation of Molecular Recognition in Solids: Chloroform-Cryptophane Complexes[J]. J. Phys. Chem. B, 2004,108(18): 5572-5581.
[9] P E GEORGHIOU, TRAN A H, STROUD S S, THOMPSON D W. Supramolecular complexation studies of [60]fullerene with calix[4]naphthalenes-a reinvestigation[J]. Tetrahedron, 2006, 62 (9): 2036-2044.
[10] CATENA G C, BRIGHT F V. The Thermodynamic Study on the Effects of eta-cyclodextrin Inclusion with Anilino-Naphthyl Sulfonates[J]. Anal. Chem. 1989, 61: 905-909.
[11] LIU Y, HAN B H, CHEN Y T. Molecular Recognition and Complexation Thermodynamics of Dye Guest Molecules by Modified Cyclodextrins and Calixarenesulfonates[J]. J. Phys. Chem. B, 2002, 106: 4678-4687.
[12] INOUE Y, YAMAMOTO K, WADA T, EVERITT S. Inclusion complexation of (cyclo)alkanes and (cyclo)alkanols with 6-O-modified cyclodextrins[J]. J.Chem. Soc, Perkin Trans.2, 1998, 8: 1807.
[13] PANG Y H, YANG L L, SHUANG S M, DONG C, THOMPSON M. Interaction of human serum albumin with bendroflumethiazide studied by fluorescence spectroscopy[J]. J. Photochem. Photobiol. B, 2005, 80(2): 139-144.
[14] POWELL H M. The structure of molecular compounds. Part IV. Clathrate compounds[J]. J. Chem. Soc, 1948, 61-73.
[15] COLLET A, DUTASTA J P, LOZACH B. Design, synthesis and properties of macrocyclic receptors for tetrahedral substrates[J]. Bull. Soc. Chim. Bel, 1990, 99: 617-633.