偶氮苯羧酸衍生物插层水滑石的结构及其性质的理论研究
|
摘要
本文采用量子化学的密度泛函理论(DFT),研究了偶氮苯羧酸衍生物(偶氮苯甲酸、偶氮苯乙酸和甲基红)插层Zn/Al水滑石的结构及其性质。一方面通过研究甲基红的顺反异构反应揭示偶氮苯羧酸衍生物的稳定性;另一方面采用分子碎片组合计算方法构建出偶氮苯羧酸衍生物插层水滑石体系的理论模型。
使用B3LYP方法,在6-31G(d,p)和6-311++G(d,p)级别上研究了甲基红的顺反异构反应机理。发现有两条反应路径,这两条路径都是既包含CNNC旋转又包含NNC反转的混合路径,并通过角度变化来说明旋转和反转对反应的贡献大小。
使用B3LYP和B3PW91方法,分别在6-31G(d,p)级别上计算了Zn/Al层板单元、偶氮苯甲酸、偶氮苯乙酸和甲基红的阴离子的电子结构,并优化得到它们分别与Zn/Al层板的主-客体相互作用体系的稳定结构。从能量、前线轨道分布等方面分析表明,以上各阴离子均易于与层板相结合形成插层结构,且插层后有利于提高客体的稳定性。
以偶氮苯甲酸、偶氮苯乙酸的聚集行为来进一步研究层间客体之间的相互作用,用B3LYP方法,在LANL2DZ和6-31G(d,p)水平上分别优化得到芳环以平行方式堆积而成的二聚体的稳定构型,它们能近似地反映客体阴离子在水滑石层间的聚集状态。
采用分子碎片组合计算方法,将分子碎片(客体-客体相互作用碎片二聚体分子和主体-客体相互作用碎片偶氮苯甲酸-Zn/Al层板、偶氮苯乙酸-Zn/Al层板)通过它们之间的紧密联系,较合理地构建出偶氮苯甲酸插层水滑石和偶氮苯乙酸插层水滑石的理论结构模型。它们在水滑石层间都为双层插层排列,得到层间距的理论值分别为1.99nm、1.78nm。
The structures and properties of azobenzoic acid derivatives (4-(phenylazo)-benzoic acid(AzBA), (4-phenylazophenyl)-acetic acid(AzAA) and methyl red(MR))-intercalated layered double hydroxide (LDHs) have been studied based on density functional theory (DFT) of quantum chemistry. The cis-trans isomerization of MR has been investigated, which shows the stability of azobenzoic acid derivatives. Furthermore, the theoretical models of LDHs have been built with a method named combinational calculation of molecular fragments (CCMF).
The cis-trans isomerization mechanism of MR has been studied by B3LYP method at the levels of 6-31G(d,p) and 6-311++G(d,p). The geometries of cis-, tran-MR and the transition states for two pathways have been optimized. It can been found that these paths both are hybrid pathways combined the CNNC rotation and the NNC inversion, and the angle changes in the reaction have shown that how they contribute to the isomerization.
From the electronic structures of Zn/Al-lamella, AzBA anion, AzAA anion and MR anion investigated by B3LYP and B3PW91 methods at the 6-31G(d,p) level, the host-guest interaction models can be built. The analysis has shown that the combination of guest anion and lamella is favored in the terms of energy and molecular frontier orbitals. The stability of guest has been enhanced after being intercalated into LDHs.
The aggregation of AzBA anion and AzAA anion has facilitated further study of guest-guest interaction. The dimer structures with parallel aromatic stacking are obtained at the levels of LANL2DZ and 6-31G(d,p) with B3LYP method, respectively, which can well reflect the aggregation states of the interlayer guest anions.
Finally, the theoretical models of AzBA-LDHs and AzAA-LDHs have been built successfully using the CCMF strategy from the combination of the guest-guest fragments and the host-guest fragments. The theoretical interlayer distances of AzBA-LDHs and AzAA-LDHs are 1.99nm and 1.78nm, respectively.
使用B3LYP方法,在6-31G(d,p)和6-311++G(d,p)级别上研究了甲基红的顺反异构反应机理。发现有两条反应路径,这两条路径都是既包含CNNC旋转又包含NNC反转的混合路径,并通过角度变化来说明旋转和反转对反应的贡献大小。
使用B3LYP和B3PW91方法,分别在6-31G(d,p)级别上计算了Zn/Al层板单元、偶氮苯甲酸、偶氮苯乙酸和甲基红的阴离子的电子结构,并优化得到它们分别与Zn/Al层板的主-客体相互作用体系的稳定结构。从能量、前线轨道分布等方面分析表明,以上各阴离子均易于与层板相结合形成插层结构,且插层后有利于提高客体的稳定性。
以偶氮苯甲酸、偶氮苯乙酸的聚集行为来进一步研究层间客体之间的相互作用,用B3LYP方法,在LANL2DZ和6-31G(d,p)水平上分别优化得到芳环以平行方式堆积而成的二聚体的稳定构型,它们能近似地反映客体阴离子在水滑石层间的聚集状态。
采用分子碎片组合计算方法,将分子碎片(客体-客体相互作用碎片二聚体分子和主体-客体相互作用碎片偶氮苯甲酸-Zn/Al层板、偶氮苯乙酸-Zn/Al层板)通过它们之间的紧密联系,较合理地构建出偶氮苯甲酸插层水滑石和偶氮苯乙酸插层水滑石的理论结构模型。它们在水滑石层间都为双层插层排列,得到层间距的理论值分别为1.99nm、1.78nm。
The structures and properties of azobenzoic acid derivatives (4-(phenylazo)-benzoic acid(AzBA), (4-phenylazophenyl)-acetic acid(AzAA) and methyl red(MR))-intercalated layered double hydroxide (LDHs) have been studied based on density functional theory (DFT) of quantum chemistry. The cis-trans isomerization of MR has been investigated, which shows the stability of azobenzoic acid derivatives. Furthermore, the theoretical models of LDHs have been built with a method named combinational calculation of molecular fragments (CCMF).
The cis-trans isomerization mechanism of MR has been studied by B3LYP method at the levels of 6-31G(d,p) and 6-311++G(d,p). The geometries of cis-, tran-MR and the transition states for two pathways have been optimized. It can been found that these paths both are hybrid pathways combined the CNNC rotation and the NNC inversion, and the angle changes in the reaction have shown that how they contribute to the isomerization.
From the electronic structures of Zn/Al-lamella, AzBA anion, AzAA anion and MR anion investigated by B3LYP and B3PW91 methods at the 6-31G(d,p) level, the host-guest interaction models can be built. The analysis has shown that the combination of guest anion and lamella is favored in the terms of energy and molecular frontier orbitals. The stability of guest has been enhanced after being intercalated into LDHs.
The aggregation of AzBA anion and AzAA anion has facilitated further study of guest-guest interaction. The dimer structures with parallel aromatic stacking are obtained at the levels of LANL2DZ and 6-31G(d,p) with B3LYP method, respectively, which can well reflect the aggregation states of the interlayer guest anions.
Finally, the theoretical models of AzBA-LDHs and AzAA-LDHs have been built successfully using the CCMF strategy from the combination of the guest-guest fragments and the host-guest fragments. The theoretical interlayer distances of AzBA-LDHs and AzAA-LDHs are 1.99nm and 1.78nm, respectively.
引文
[1]Vaccari A.Preparation and catalytic properties of cationic and anionic clays[J].Catal.Today,1998,41:53-71
[2]杜以波,Evans D G,孙鹏,等.阴离子型层柱材料研究进展[J].化学通报,2000,5:20-24
[3]孟锦宏,张慧,王治强,等.插层组装超分子结构有机物柱撑阴离子层状材料[J].化学通报,2003,66(2):85-94
[4]Feitknecht W,Gerber W.Double hydroxides and basic double salts(Ⅲ) Mg-Al double hydroxides[J].Helv.Chim.Aeta.Ibid.,1942,25:131-137
[5]Feitkneeht W.Formation of double hydroxides between bi- and trivalent metals[J].Helv.Chim.Acta.,1942,25:555-569
[6]Cavani F,Trifiro F,Vaceari A.Hydrotalcite-type anionic clays:preparation,properties and applications[J].Catal.Today,1991,11:173-301
[7]Constantino V R L,Pinnavaia T J.Structure-reactivity relationships for basic catalysts derived from a Mg~(2+)/Al~(3+)/CO_3~(2-) layered double hydroxide[J].Catal.Lett.,1994,23,361-368
[8]Bone K S.Ph.D.report:Development and Charaeterisation of the Interlayer Chemistry of Layerde Double Hydroxides[R].Univ.of Exeter,1995
[9]袁琦.L型氨基酸插层水滑石的制备及其性能研究[D].北京:北京化工大学,2004
[10]邢颖,李殿卿,郭灿雄,等.Zn-Al-CO_3水滑石晶粒尺寸控制与光屏蔽作用研究[J].精细化工,2003,20(1):1-7
[11]Zhao Y,Li F,Zhang R,et al.Preparation of layered double-hydroxide nanomaterials with a uniform crystallite size using a new method involving separate nucleation and aging steps[J].Chem.Mater.,2002,14(10):4286-4291
[12]Bellotto M,Rebours B,Clause O,et al.Hydrotalcite decomposition mechanism:a clue to the structure and reactivity of spinel-like mixed oxides[J].J.Phys.Chem.,1996,100(20):8535-8542
[13]段雪,张法智.插层组装与功能材料[M].北京:化学工业出版社,2007
[14]Leroux F,Taviot-Gueho C.Fine tuning between organic and inorganic host structure:new trend in layered double hydroxide hybrid assemblies[J].J.Mater.Chem.,2005,15:3628-3642
[15]张慧,齐荣,刘丽娜,等.镁铁双羟基复合金属氧化物的可控合成及晶面生长特征研究[J].化学物理学报,2003,16(1):45-50
[16]Feng Y J,Li D Q,Li C X,et al.Synthesis of Cu-containing layered double hydroxides with a narrow crystallite-size distribution[J].Clay Clay Miner,2003,51:566-569
[17]Evans D G,Duan X.Preparation of layered double hydroxides and their application as additives in polymers,as precursors to magnetic materials and in biology and medicine[J].Chem.Commom.,2006:485-496
[19]Pausch I,Lohse H H,Sehurmann K,et al.Synthesis of disordered and Al-rich hydrotalcite-like compounds[J].Clay Clay Miner.,1986,34:507-511
[20]Khan A I,O'Hare D.Intercalation chemistry of layered double hydroxides:recent developments and applications[J].J.Mater.Chem.,2002,12:3191-3198
[21]Newman S P,Jones W.Synthesis,characterization and application of layered double hydroxides containing organic guests[J].New J.Chem.,1998,22:105-115
[22]Meyn M,Beneke K,Lagaly G.Anion-exchange reactions of layered double hydroxides[J].Inorg.Chem.,1990,29:5201-5207
[23]Carlino S,Hudson M J.Reaction of molten sebacic acid with a(Mg/Al) layered double hydroxide[J].J.Mater.Chem.,1994,4(1):99-104
[24]任玲玲,何静,段雪.阴离子型层柱材料的插层主装[J].化学通报,2001,11:686-691
[25]杜以波,何静,李峰,等.微波技术在制备水滑石和柱撑水滑石中的应用[J].应用科学学报,1989,16(3):349-354.
[26]谢晖,矫庆泽,段雪.镁铝型水滑石水热合成[J].应用化学,2001,18(1):70-72
[27]Kohjiyo S,Sato T,Nakayama T.Polymerization of propylene oxide by calcined synthetic hydrotalcite[J].Makromol Chem.Rapid Commun.,1981,2:231-233
[28]Reichle W T.Pulse microreactor examination of the vapor-phase aldol condensation of acetone[J].J.Catal.,1980,63:295-306
[29]Drezdzon M A.Synthesis of isopolymetalate-pillared hydrotalcite via organic anion pillared precursors[J].Inorg.Chem.,1988,27:4628-4632
[30]吕亮,吾国强,段雪,等.水滑石的制备、表征及其在酯交换反应中的应用[J].精细石油化工,2001,1:9-12
[31]Choudary B M,Kantam M L,Venkat,et al.The first example of Michael addition catalysed by modified Mg-Al hydrotalcite[J].J.Mol.Catal.A,1999,146:279-284
[32]Gusi S.Trifiro F,Vaccari A,et al.Catalysts for low-temperature methanol synthesis[J].J.Catal.,1985,94:120-127
[33]胡长文,李丹峰,郭伊荇,等.超分子层柱双氢氧化物[J].科学通报,2001,46:359-364
[34]Twu J,Durra P K.Decavanadate ion-pillared hydrotalcite-spectroscopic studies of the thermal-decomposition process[J].J.Catal.,1990,124:503-510
[35]Dutta T K,Puff M.Anion exchange in lithium aluminate hydroxides[J].J.Phys.Chem.,1989,93:376-381
[36]李连生.高等学校化学学报[J].1995,8:1164-1167
[37]Guo Y H,Wang Y H,Hu C W,et al.Microporous polyoxometalates POMs/SiO_2:synthesis and photocatalytic degradation of aqueous organoeholorine pesticides[J].Chem.Mater.,2000,12:3501-3508
[38]Guo Y H,Li D F,Hu C W,et al.Photocatalytic degredation of aqueous organocholorine pesticide on the layered double hydroxide pillared by paratungstate anion,[Mg_2Al_6(OH)_(36)(W_7O_(24))·4H_2O][J].Appl.Catal.B,2001,30:337-349
[39]Nishimura T,Kakiuchi N,Inoue M,et al.Palladium(Ⅱ)-supported hydrotalcite as a catalyst for selective oxidation of alcohols using molecular oxygen[J].Chem.Commun.,2000,1245
[40]Rytter E,Akporiaye D,Olsbye U.Catalyst support material[P].US Patent,6313063.2001-11-06
[41]McKay I,Ciupa A,Chisholm P.Heterogeneous metallocene catalyst[P].US Patent,6235671.2001-05-22
[42]Chin A A,Johnson I D,Kresge C T,et al.Additive for vanadium capture in catalytic cracking[P].US Patent,4889615.1989-12-26
[43]Gob K H,Lira T T,Dong Z.Application of layered double hydroxides for removal of oxyanions:a review[J].Water Res.,2008,42:1343-1368
[44]Valcheva-Travkova M L,Davidova N,Weiss A H.Thermal-decomposition of the PB,al-hydrotalcite material[J].J.Mater.Sci.,1995,30:737-743
[45]Ulibarri M A,Pavlovic I,Cornijo J,et al.Hydrotalcite-like compounds as potential sorbents of phenols from water[J].Appl.Clay Sci.,1995,10(1-2):131-145
[46]Dutta T K,Puri M.Anion exchange in lithium aluminate hydroxides[J].J.Phys.Chem.,1989,93:376-381
[47]Costantino U,Nocchetti M.Layered double hydroxides and their intercalation compounds in photochemistry and medicinal chemistry[M].NY Nova Sci Publish,2001
[48]White J L,Hem S L.Ind.Eng.Chem.Prod.Res.Dev.,1983,22:665-671
[49]Miyata S.Gastric antacid and method for controlling pH of gastric juice[P].US Patent.4514389.1985-04-30
[50]Khan A I,Lei L X,Norquist A J,et al.Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide[J].Chem.Commun.,2001,22:2342-2343
[51]Ambrogi V,Fardella G,Grandolini G,et al.Intercalation compounds of hydrotalcite-like anionic clays with anti-inflammatory agents-I.Intercalation and in vitro release of ibuprofen[J].Int.J.Pharm.,2001,220:23-32
[52]Ogawa M,Kuroda K.Photofunctions of intercalation compounds[J].Chem.Rev.,1995,95(2):399-438
[53]Peterson R C,Hill R J,Gibbs G V.A molecular-orbital study of distortion in the layer structure brucite,gibbsite and serpentine[J].Can.Mineral,1979,17:703-711
[54]Sato H,Morita A,Onto K,et al.Templating effects on the mineralization of layered inorganic compounds:(1) density functional calculation of the formation of single-layered magnesium hydroxide as a brucite model[J].Langmuir,2003,19:7120-7129
[55]Pu M,Zhang B F.Theoretical study on the microstructures of hydrotalcite lamellae with Mg/Al ratio of two[J].Mater.Lett.,2005,59:3343-3347
[56]Pu M,Wang Y L,Liu L Y,et al.Quantum chemistry and molecular mechanics studies of the lamella structure of hydrotalcite with Mg/Al ratio of 3[J].J.Phys.Chem.Solids,2008,69:1066-1069
[57]Greenwell H C,Stackhouse S,Coveney P V,et al.A density functional theory study of catalytic trans-esterification by tert-butoxide MgAl anionic clays[J].J.Phys.Chem.B,2002,106:3476-3485
[58]倪哲明,潘国祥,王力耕,等.LDHs主体层板与卤素阴离子超分子作用的理论研究[J].物理化学学报,2006,22:1321-1324
[59]Reinke N,Fuhrmann T,Perschke A,et al.Improved outcoupling of light in organic light emitting devices,utilizing a holographic DFB-structure[J].J.Luminescence,2004,110:413-417
[60]Banerjee I A,Yu L,Matsui H.Application of host-guest chemistry in nanotube-based device fabrication photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition[J].J.Am.Chem.Soc.,2003,125:9542-9543
[61]Shin H K,Kim J M,Kwon Y S,et al.Optical behavior and surface morphology of the zaobenzene functionalized dedrimer in Langmuir and Langmuir-Blodgett monolayers[J].Opt.Mater.,2002,21:389-394
[62]dos Santos D S Jr,Bassi A,Rodrigues J J Jr,et al.Light-induced storage in layer-by-layer films of chitosan and an azo dye[J].Biomacromolecules,2003,4:1502-1505
[63]Haralampus-Grynaviski N M,Johnson L J,Firestone M A.Photochromic and optical birefringence properties of azo-dye-doped polymer-grafted lipid-based complex fluids[J].Macromolecules,2005,38:8971-8974
[64]dos Reis M J,Silverio F,Tronto J,et al.Effects of pH,temperature,and ionic strength on adsorption of sodium dodecylbenzenesulfonate into Mg-Al-CO_3 layered double hydroxides[J].J.Phys.Chem.Solids,2004,65:487-492
[65]Reinke N,Fuhrmann T,Perschke A,et al.Improved outcoupling of light in organic light emitting devices,utilizing a holographic DFB-structure[J].J.Luminescence,2004,110:413-417
[66]Ikawa T,Hoshino F,Matsuyama T,et al.Molecular-shape imprinting and immobilization of biomolecules on a polymer containing azo dye[J].Langmuir,2006,22:2747-2753
[67]Latterini L,Nocchetti M,Aloisi G G,et al.Organized chromophores in layered inorganic matrices[J].Inorg.Chim.Acta,2007,360:728-740
[68]Iyi N,Kurashima K,Fujita T.Orientation of an organic anion and second-staging structure in layered double-hydroxide intercalates[J].Chem.Mater.,2002,14:583-589
[69]Tian Y,Wang G,Li F,et al.Synthesis and thermo-optical stability of o-methyl red-intercalated Ni-Fe layered double hydroxide material[J].Mater.Lett.,2007,61:1662-1666
[70]Liu J Q.Study on preparation and properties of layered metal hydroxide supramolecular nanocomposite material[D],济南:山东大学,2006
[71]谈国霞,吴磊磊.量子化学发展综述[J].科技信息(高校理科研究),2007,36:441
[72]程建波.几种分子组装体振动光谱的密度泛函理论研究[D].吉林:吉林大学,2005
[73]Pople J A.Ab initio molecular orbital theory[J].J.Chem.Phys.,1965,43:8136-8144
[74]江元生.近似分子轨道理论方法[M].北京:科学出版社,1976,77-82
[75]Ridley J E,Zemer M C.The Hartree-Fock approximation[J].Theoret.Chim.Acta,1976,42:223-232
[76]周公度,段连运.结构化学基础[M].北京:北京大学出版社,2008,第四版
[77]唐敖庆,杨忠志,李前树.量子化学[M].北京:科学出版社,1982
[78]徐光宪,黎乐民,王德民.量子化学基本原理和从头计算法[M].北京:科学出版社,1985
[79]Hartree D.Calculations of atomic structure[M].New York:Wiley,1957
[80]Roothaan C C J.New developments in molecular orbital theory[J].Rev.Mod.Phys.,1951,23:69-89
[81]Parr R G,Yang W.Density-functional theory of atoms and molecules[M].Oxford University Press:Oxfird,1989
[82]赵成大.固体量子化学—材料化学的理论基础[M].北京:高等教育出版社,2003,第二版
[83]Labanowski J K,Andzelm J.Density functional methods in chemistry[M].Springer-Vedag:New York,1991
[84]Hohenberg P,Kohn W.Inhomogeneous electron gas[J].Phys.Rev.,1964,136:B864-B871
[85]Kohn W,Sham L J.Self-consistent equations including exchange and correlation effects[J].Phys.Rev.,1965,140:A1133-A1138
[86]Slater J C.Quantum theory of molecular and solids[M].New York:McGraw-Hill,1974
[87]Salahub D R,Zerner M C.The challenge of d and f electrons:theory and computation[M]. Washington D C:American Chemical Society,1989
[88]Parr R G,Yang W.Density-functional theory of atoms and molecules[M].Oxford:Oxford Univ.Press,1989
[89]Pople J A,Gill P W M,Johnson B G.Kohn-Sham density functional theory within a finite basis set[J].Chem.Phys.Lett.,1992,199:557-560
[90]Labanowski J K,Andzelm J W.Density functional methods in chemistry[M].New York:Springer-Verlag,1991
[91]Stern M J,Persky A,Klein F S.Force field and tunneling effects in the H-H-Cl reaction system.Determination from kinetic-isotope-effect measurements[J].J.Chem.Phys.,1973,58:5697-5706
[92]Garrett B C,Truhlar D G.Generalized transition state theory.Classical mechanical theory and applications to collinear reactions of hydrogen molecules[J].J.Phys.Chem.,1979,83:1052-1079
[93]Garrett B C,Truhlar D G.Additions and corrections-generalized transition state theory.Quantum effects for collinear reactions of hydrogen molecules[J].J.Phys.Chem.,1983,87:4553-4553
[94]Wynne-Jones W F K,Eyring H.The absolute rate of reactions in condensed phases[J].J.Chem.Phys.,1935,3:492-502
[95]赵学庄,等编著,化学反应动力学原理(下册)[M].北京:高等教育出版社,1990
[96]Fukui K,Tachibana A,Yamashita K.Toward chemodynamics[J].Int.J.Quantum.Chem.,1981,15:621-632
[97]Ishida K,Morokuma K,Komornicki A.The intrinsic reaction coordinate.An ab initio calculation for HNC-HCN and H~-+CH_4→CH_4+H~-[J].J.Chem.Phys.,1977,66:2153-2156
[98]Eyring H,Lin S H,Lin S M.Basic Chemical Kinetics[M].John Wiley and Sons,1980
[99]Truhlar D G,Garrett B C,Klippenstein S J.Current status of transition-state theroy[J].J.Phys.Chem.,1996,100:12771-12800
[100]许洪涛.含偶氮聚合物薄膜光致各向异性特性的研究[D].上海:上海交通大学,2007
[101]Monti S,Orlandi G,Palmieri P.Features of the photochemically active state surfaces of azobenzene[J].Chem.Phys.,1982,71(1):87-99
[102]Cattaneo P,Persico M.An ab initio study of the photochemistry of azobenzene[J].Phys.Chem.Chem.Phys.,1999,1:4739-4743
[103]Blevins A A,Blanehard G J.Effect of positional substitution on the optical response of symmetrically disubstituted azobenzene derivatives[J].J.Phys.Chem.,2004,108(16):4962-4968
[104]Crecca C R,Roitberg A E.Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives[J].J.Phys.Chem.A,2006,110:8188-8203
[105]Wang L,Wang X.An ab initio study of stable conformation and thermal isomerization of p-aminoazobenzene[J].J.Mol.Struet.(Theochem),2007,806:179-186
[106]Asano T,Okada T.Further kinetic evidence for the competitive rotational and inversional Z-E isomerization of substituted azobenzenes[J].J.Org.Chem.,1986,51(23):4454-4458
[107]Shin D M,Whitten D G.Solvent-induced mechanism change in charge-transfer molecules.Inversion versus rotation paths for the Z→E isomerization of donor-acceptor substituted azobenzenes[J].J.Am.Chem.Soc.,1988,110(15):5206-5208
[108]Azuki M,Morihashi K,Watanabe T,et al.Ab initio GB study of the acid-catalyzed cis-trans isomerization of methyl yellow and methyl orange in aqueous solution[J].J.Mol.Struct.(Theochem),2001,542(1-3):255-262
[109]Becke A D,Density functional thermochemistry(Ⅲ):The role of exact exchange[J].J.Chem.Phys.,1993,98:5648
[110]Lee C,Yang W,Parr R G.Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J].Phys.Rev.B,1988,37:785-789
[111]Gonzalez C,Schlegel H B.An improved algorithm for reaction-path following[J].J.Chem.Phys.,1989,90:2154-2161
[112]Gonzalez C,Schlegel H B.Reaction-path following in mass-weighted internal coordinates[J].J.Phys.Chem.,1990,94:5523-5527
[113]Frisch M J,Trucks G W,Schlegel H B,et al.Gaussian 03,Revision B.04,Gaussian,Inc.,Pittsburgh PA,2003
[114]Eigen M.and DeMaeyer L.,"Technique of Organic Chemistry." Vol.Ⅷ,Part Ⅱ,S.L.Friess,E.S.Lewis,and A.Weissberger,Ed.,Interscience Publishers,New York,N.Y.,1963,Chapter 18
[115]Srour R K,McDonald L M,Determination of the acidity constants of methyl red and phenol red indicators in binary methanol- and ethanol-water mixtures[J],J.Chem.Eng.Data,2008,53:116-127
[116]Khoo I C,Slussarenko S,Guenther B D,et al.Optically inducedspace-charge fields,de voltage,and extraordinarilylarge nonlinearity in dye-doped nematic liquid crystals[J].Opt.Lett.,1998,23:253-255
[117]蒋建伟.表面增强拉曼散射在研究几种偶氮染料分子吸附特性中的应用[D],开封:河南大学,2005
[118]Kuwabara T,Nakajima H,Nanasawa M,et al.Color change indicators for molecules using methyl red-modified cyclodextrins[J].Anal.Chem.,1999,71:2844-2849
[119]Reilley C N,Smith E M.Chemical application of complementary tristimulus colorimetry[J].Anal.Chem.,1960,32(10):1233-1240
[120]Ramette R W,Dratz E A,Kelly P W.Acid-base equilibria of methyl red[J].J.Phys.Chem.,1962,66(3):527-532
[121]Seu G.Spectrophotometric study of the prototropic equilibrium of methyl red in organic solvent[J].Dyes Pigments,1995,29(3):227-240
[122]周公度,段连运.结构化学基础[M].第四版.北京:北京大学出版社,2008:324
[123]刘灵燕.酸性橙Ⅱ水滑石插层结构的实验与理论研究[D].北京:北京化工大学,2008
[2]杜以波,Evans D G,孙鹏,等.阴离子型层柱材料研究进展[J].化学通报,2000,5:20-24
[3]孟锦宏,张慧,王治强,等.插层组装超分子结构有机物柱撑阴离子层状材料[J].化学通报,2003,66(2):85-94
[4]Feitknecht W,Gerber W.Double hydroxides and basic double salts(Ⅲ) Mg-Al double hydroxides[J].Helv.Chim.Aeta.Ibid.,1942,25:131-137
[5]Feitkneeht W.Formation of double hydroxides between bi- and trivalent metals[J].Helv.Chim.Acta.,1942,25:555-569
[6]Cavani F,Trifiro F,Vaceari A.Hydrotalcite-type anionic clays:preparation,properties and applications[J].Catal.Today,1991,11:173-301
[7]Constantino V R L,Pinnavaia T J.Structure-reactivity relationships for basic catalysts derived from a Mg~(2+)/Al~(3+)/CO_3~(2-) layered double hydroxide[J].Catal.Lett.,1994,23,361-368
[8]Bone K S.Ph.D.report:Development and Charaeterisation of the Interlayer Chemistry of Layerde Double Hydroxides[R].Univ.of Exeter,1995
[9]袁琦.L型氨基酸插层水滑石的制备及其性能研究[D].北京:北京化工大学,2004
[10]邢颖,李殿卿,郭灿雄,等.Zn-Al-CO_3水滑石晶粒尺寸控制与光屏蔽作用研究[J].精细化工,2003,20(1):1-7
[11]Zhao Y,Li F,Zhang R,et al.Preparation of layered double-hydroxide nanomaterials with a uniform crystallite size using a new method involving separate nucleation and aging steps[J].Chem.Mater.,2002,14(10):4286-4291
[12]Bellotto M,Rebours B,Clause O,et al.Hydrotalcite decomposition mechanism:a clue to the structure and reactivity of spinel-like mixed oxides[J].J.Phys.Chem.,1996,100(20):8535-8542
[13]段雪,张法智.插层组装与功能材料[M].北京:化学工业出版社,2007
[14]Leroux F,Taviot-Gueho C.Fine tuning between organic and inorganic host structure:new trend in layered double hydroxide hybrid assemblies[J].J.Mater.Chem.,2005,15:3628-3642
[15]张慧,齐荣,刘丽娜,等.镁铁双羟基复合金属氧化物的可控合成及晶面生长特征研究[J].化学物理学报,2003,16(1):45-50
[16]Feng Y J,Li D Q,Li C X,et al.Synthesis of Cu-containing layered double hydroxides with a narrow crystallite-size distribution[J].Clay Clay Miner,2003,51:566-569
[17]Evans D G,Duan X.Preparation of layered double hydroxides and their application as additives in polymers,as precursors to magnetic materials and in biology and medicine[J].Chem.Commom.,2006:485-496
[19]Pausch I,Lohse H H,Sehurmann K,et al.Synthesis of disordered and Al-rich hydrotalcite-like compounds[J].Clay Clay Miner.,1986,34:507-511
[20]Khan A I,O'Hare D.Intercalation chemistry of layered double hydroxides:recent developments and applications[J].J.Mater.Chem.,2002,12:3191-3198
[21]Newman S P,Jones W.Synthesis,characterization and application of layered double hydroxides containing organic guests[J].New J.Chem.,1998,22:105-115
[22]Meyn M,Beneke K,Lagaly G.Anion-exchange reactions of layered double hydroxides[J].Inorg.Chem.,1990,29:5201-5207
[23]Carlino S,Hudson M J.Reaction of molten sebacic acid with a(Mg/Al) layered double hydroxide[J].J.Mater.Chem.,1994,4(1):99-104
[24]任玲玲,何静,段雪.阴离子型层柱材料的插层主装[J].化学通报,2001,11:686-691
[25]杜以波,何静,李峰,等.微波技术在制备水滑石和柱撑水滑石中的应用[J].应用科学学报,1989,16(3):349-354.
[26]谢晖,矫庆泽,段雪.镁铝型水滑石水热合成[J].应用化学,2001,18(1):70-72
[27]Kohjiyo S,Sato T,Nakayama T.Polymerization of propylene oxide by calcined synthetic hydrotalcite[J].Makromol Chem.Rapid Commun.,1981,2:231-233
[28]Reichle W T.Pulse microreactor examination of the vapor-phase aldol condensation of acetone[J].J.Catal.,1980,63:295-306
[29]Drezdzon M A.Synthesis of isopolymetalate-pillared hydrotalcite via organic anion pillared precursors[J].Inorg.Chem.,1988,27:4628-4632
[30]吕亮,吾国强,段雪,等.水滑石的制备、表征及其在酯交换反应中的应用[J].精细石油化工,2001,1:9-12
[31]Choudary B M,Kantam M L,Venkat,et al.The first example of Michael addition catalysed by modified Mg-Al hydrotalcite[J].J.Mol.Catal.A,1999,146:279-284
[32]Gusi S.Trifiro F,Vaccari A,et al.Catalysts for low-temperature methanol synthesis[J].J.Catal.,1985,94:120-127
[33]胡长文,李丹峰,郭伊荇,等.超分子层柱双氢氧化物[J].科学通报,2001,46:359-364
[34]Twu J,Durra P K.Decavanadate ion-pillared hydrotalcite-spectroscopic studies of the thermal-decomposition process[J].J.Catal.,1990,124:503-510
[35]Dutta T K,Puff M.Anion exchange in lithium aluminate hydroxides[J].J.Phys.Chem.,1989,93:376-381
[36]李连生.高等学校化学学报[J].1995,8:1164-1167
[37]Guo Y H,Wang Y H,Hu C W,et al.Microporous polyoxometalates POMs/SiO_2:synthesis and photocatalytic degradation of aqueous organoeholorine pesticides[J].Chem.Mater.,2000,12:3501-3508
[38]Guo Y H,Li D F,Hu C W,et al.Photocatalytic degredation of aqueous organocholorine pesticide on the layered double hydroxide pillared by paratungstate anion,[Mg_2Al_6(OH)_(36)(W_7O_(24))·4H_2O][J].Appl.Catal.B,2001,30:337-349
[39]Nishimura T,Kakiuchi N,Inoue M,et al.Palladium(Ⅱ)-supported hydrotalcite as a catalyst for selective oxidation of alcohols using molecular oxygen[J].Chem.Commun.,2000,1245
[40]Rytter E,Akporiaye D,Olsbye U.Catalyst support material[P].US Patent,6313063.2001-11-06
[41]McKay I,Ciupa A,Chisholm P.Heterogeneous metallocene catalyst[P].US Patent,6235671.2001-05-22
[42]Chin A A,Johnson I D,Kresge C T,et al.Additive for vanadium capture in catalytic cracking[P].US Patent,4889615.1989-12-26
[43]Gob K H,Lira T T,Dong Z.Application of layered double hydroxides for removal of oxyanions:a review[J].Water Res.,2008,42:1343-1368
[44]Valcheva-Travkova M L,Davidova N,Weiss A H.Thermal-decomposition of the PB,al-hydrotalcite material[J].J.Mater.Sci.,1995,30:737-743
[45]Ulibarri M A,Pavlovic I,Cornijo J,et al.Hydrotalcite-like compounds as potential sorbents of phenols from water[J].Appl.Clay Sci.,1995,10(1-2):131-145
[46]Dutta T K,Puri M.Anion exchange in lithium aluminate hydroxides[J].J.Phys.Chem.,1989,93:376-381
[47]Costantino U,Nocchetti M.Layered double hydroxides and their intercalation compounds in photochemistry and medicinal chemistry[M].NY Nova Sci Publish,2001
[48]White J L,Hem S L.Ind.Eng.Chem.Prod.Res.Dev.,1983,22:665-671
[49]Miyata S.Gastric antacid and method for controlling pH of gastric juice[P].US Patent.4514389.1985-04-30
[50]Khan A I,Lei L X,Norquist A J,et al.Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide[J].Chem.Commun.,2001,22:2342-2343
[51]Ambrogi V,Fardella G,Grandolini G,et al.Intercalation compounds of hydrotalcite-like anionic clays with anti-inflammatory agents-I.Intercalation and in vitro release of ibuprofen[J].Int.J.Pharm.,2001,220:23-32
[52]Ogawa M,Kuroda K.Photofunctions of intercalation compounds[J].Chem.Rev.,1995,95(2):399-438
[53]Peterson R C,Hill R J,Gibbs G V.A molecular-orbital study of distortion in the layer structure brucite,gibbsite and serpentine[J].Can.Mineral,1979,17:703-711
[54]Sato H,Morita A,Onto K,et al.Templating effects on the mineralization of layered inorganic compounds:(1) density functional calculation of the formation of single-layered magnesium hydroxide as a brucite model[J].Langmuir,2003,19:7120-7129
[55]Pu M,Zhang B F.Theoretical study on the microstructures of hydrotalcite lamellae with Mg/Al ratio of two[J].Mater.Lett.,2005,59:3343-3347
[56]Pu M,Wang Y L,Liu L Y,et al.Quantum chemistry and molecular mechanics studies of the lamella structure of hydrotalcite with Mg/Al ratio of 3[J].J.Phys.Chem.Solids,2008,69:1066-1069
[57]Greenwell H C,Stackhouse S,Coveney P V,et al.A density functional theory study of catalytic trans-esterification by tert-butoxide MgAl anionic clays[J].J.Phys.Chem.B,2002,106:3476-3485
[58]倪哲明,潘国祥,王力耕,等.LDHs主体层板与卤素阴离子超分子作用的理论研究[J].物理化学学报,2006,22:1321-1324
[59]Reinke N,Fuhrmann T,Perschke A,et al.Improved outcoupling of light in organic light emitting devices,utilizing a holographic DFB-structure[J].J.Luminescence,2004,110:413-417
[60]Banerjee I A,Yu L,Matsui H.Application of host-guest chemistry in nanotube-based device fabrication photochemically controlled immobilization of azobenzene nanotubes on patterned α-CD monolayer/Au substrates via molecular recognition[J].J.Am.Chem.Soc.,2003,125:9542-9543
[61]Shin H K,Kim J M,Kwon Y S,et al.Optical behavior and surface morphology of the zaobenzene functionalized dedrimer in Langmuir and Langmuir-Blodgett monolayers[J].Opt.Mater.,2002,21:389-394
[62]dos Santos D S Jr,Bassi A,Rodrigues J J Jr,et al.Light-induced storage in layer-by-layer films of chitosan and an azo dye[J].Biomacromolecules,2003,4:1502-1505
[63]Haralampus-Grynaviski N M,Johnson L J,Firestone M A.Photochromic and optical birefringence properties of azo-dye-doped polymer-grafted lipid-based complex fluids[J].Macromolecules,2005,38:8971-8974
[64]dos Reis M J,Silverio F,Tronto J,et al.Effects of pH,temperature,and ionic strength on adsorption of sodium dodecylbenzenesulfonate into Mg-Al-CO_3 layered double hydroxides[J].J.Phys.Chem.Solids,2004,65:487-492
[65]Reinke N,Fuhrmann T,Perschke A,et al.Improved outcoupling of light in organic light emitting devices,utilizing a holographic DFB-structure[J].J.Luminescence,2004,110:413-417
[66]Ikawa T,Hoshino F,Matsuyama T,et al.Molecular-shape imprinting and immobilization of biomolecules on a polymer containing azo dye[J].Langmuir,2006,22:2747-2753
[67]Latterini L,Nocchetti M,Aloisi G G,et al.Organized chromophores in layered inorganic matrices[J].Inorg.Chim.Acta,2007,360:728-740
[68]Iyi N,Kurashima K,Fujita T.Orientation of an organic anion and second-staging structure in layered double-hydroxide intercalates[J].Chem.Mater.,2002,14:583-589
[69]Tian Y,Wang G,Li F,et al.Synthesis and thermo-optical stability of o-methyl red-intercalated Ni-Fe layered double hydroxide material[J].Mater.Lett.,2007,61:1662-1666
[70]Liu J Q.Study on preparation and properties of layered metal hydroxide supramolecular nanocomposite material[D],济南:山东大学,2006
[71]谈国霞,吴磊磊.量子化学发展综述[J].科技信息(高校理科研究),2007,36:441
[72]程建波.几种分子组装体振动光谱的密度泛函理论研究[D].吉林:吉林大学,2005
[73]Pople J A.Ab initio molecular orbital theory[J].J.Chem.Phys.,1965,43:8136-8144
[74]江元生.近似分子轨道理论方法[M].北京:科学出版社,1976,77-82
[75]Ridley J E,Zemer M C.The Hartree-Fock approximation[J].Theoret.Chim.Acta,1976,42:223-232
[76]周公度,段连运.结构化学基础[M].北京:北京大学出版社,2008,第四版
[77]唐敖庆,杨忠志,李前树.量子化学[M].北京:科学出版社,1982
[78]徐光宪,黎乐民,王德民.量子化学基本原理和从头计算法[M].北京:科学出版社,1985
[79]Hartree D.Calculations of atomic structure[M].New York:Wiley,1957
[80]Roothaan C C J.New developments in molecular orbital theory[J].Rev.Mod.Phys.,1951,23:69-89
[81]Parr R G,Yang W.Density-functional theory of atoms and molecules[M].Oxford University Press:Oxfird,1989
[82]赵成大.固体量子化学—材料化学的理论基础[M].北京:高等教育出版社,2003,第二版
[83]Labanowski J K,Andzelm J.Density functional methods in chemistry[M].Springer-Vedag:New York,1991
[84]Hohenberg P,Kohn W.Inhomogeneous electron gas[J].Phys.Rev.,1964,136:B864-B871
[85]Kohn W,Sham L J.Self-consistent equations including exchange and correlation effects[J].Phys.Rev.,1965,140:A1133-A1138
[86]Slater J C.Quantum theory of molecular and solids[M].New York:McGraw-Hill,1974
[87]Salahub D R,Zerner M C.The challenge of d and f electrons:theory and computation[M]. Washington D C:American Chemical Society,1989
[88]Parr R G,Yang W.Density-functional theory of atoms and molecules[M].Oxford:Oxford Univ.Press,1989
[89]Pople J A,Gill P W M,Johnson B G.Kohn-Sham density functional theory within a finite basis set[J].Chem.Phys.Lett.,1992,199:557-560
[90]Labanowski J K,Andzelm J W.Density functional methods in chemistry[M].New York:Springer-Verlag,1991
[91]Stern M J,Persky A,Klein F S.Force field and tunneling effects in the H-H-Cl reaction system.Determination from kinetic-isotope-effect measurements[J].J.Chem.Phys.,1973,58:5697-5706
[92]Garrett B C,Truhlar D G.Generalized transition state theory.Classical mechanical theory and applications to collinear reactions of hydrogen molecules[J].J.Phys.Chem.,1979,83:1052-1079
[93]Garrett B C,Truhlar D G.Additions and corrections-generalized transition state theory.Quantum effects for collinear reactions of hydrogen molecules[J].J.Phys.Chem.,1983,87:4553-4553
[94]Wynne-Jones W F K,Eyring H.The absolute rate of reactions in condensed phases[J].J.Chem.Phys.,1935,3:492-502
[95]赵学庄,等编著,化学反应动力学原理(下册)[M].北京:高等教育出版社,1990
[96]Fukui K,Tachibana A,Yamashita K.Toward chemodynamics[J].Int.J.Quantum.Chem.,1981,15:621-632
[97]Ishida K,Morokuma K,Komornicki A.The intrinsic reaction coordinate.An ab initio calculation for HNC-HCN and H~-+CH_4→CH_4+H~-[J].J.Chem.Phys.,1977,66:2153-2156
[98]Eyring H,Lin S H,Lin S M.Basic Chemical Kinetics[M].John Wiley and Sons,1980
[99]Truhlar D G,Garrett B C,Klippenstein S J.Current status of transition-state theroy[J].J.Phys.Chem.,1996,100:12771-12800
[100]许洪涛.含偶氮聚合物薄膜光致各向异性特性的研究[D].上海:上海交通大学,2007
[101]Monti S,Orlandi G,Palmieri P.Features of the photochemically active state surfaces of azobenzene[J].Chem.Phys.,1982,71(1):87-99
[102]Cattaneo P,Persico M.An ab initio study of the photochemistry of azobenzene[J].Phys.Chem.Chem.Phys.,1999,1:4739-4743
[103]Blevins A A,Blanehard G J.Effect of positional substitution on the optical response of symmetrically disubstituted azobenzene derivatives[J].J.Phys.Chem.,2004,108(16):4962-4968
[104]Crecca C R,Roitberg A E.Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives[J].J.Phys.Chem.A,2006,110:8188-8203
[105]Wang L,Wang X.An ab initio study of stable conformation and thermal isomerization of p-aminoazobenzene[J].J.Mol.Struet.(Theochem),2007,806:179-186
[106]Asano T,Okada T.Further kinetic evidence for the competitive rotational and inversional Z-E isomerization of substituted azobenzenes[J].J.Org.Chem.,1986,51(23):4454-4458
[107]Shin D M,Whitten D G.Solvent-induced mechanism change in charge-transfer molecules.Inversion versus rotation paths for the Z→E isomerization of donor-acceptor substituted azobenzenes[J].J.Am.Chem.Soc.,1988,110(15):5206-5208
[108]Azuki M,Morihashi K,Watanabe T,et al.Ab initio GB study of the acid-catalyzed cis-trans isomerization of methyl yellow and methyl orange in aqueous solution[J].J.Mol.Struct.(Theochem),2001,542(1-3):255-262
[109]Becke A D,Density functional thermochemistry(Ⅲ):The role of exact exchange[J].J.Chem.Phys.,1993,98:5648
[110]Lee C,Yang W,Parr R G.Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density[J].Phys.Rev.B,1988,37:785-789
[111]Gonzalez C,Schlegel H B.An improved algorithm for reaction-path following[J].J.Chem.Phys.,1989,90:2154-2161
[112]Gonzalez C,Schlegel H B.Reaction-path following in mass-weighted internal coordinates[J].J.Phys.Chem.,1990,94:5523-5527
[113]Frisch M J,Trucks G W,Schlegel H B,et al.Gaussian 03,Revision B.04,Gaussian,Inc.,Pittsburgh PA,2003
[114]Eigen M.and DeMaeyer L.,"Technique of Organic Chemistry." Vol.Ⅷ,Part Ⅱ,S.L.Friess,E.S.Lewis,and A.Weissberger,Ed.,Interscience Publishers,New York,N.Y.,1963,Chapter 18
[115]Srour R K,McDonald L M,Determination of the acidity constants of methyl red and phenol red indicators in binary methanol- and ethanol-water mixtures[J],J.Chem.Eng.Data,2008,53:116-127
[116]Khoo I C,Slussarenko S,Guenther B D,et al.Optically inducedspace-charge fields,de voltage,and extraordinarilylarge nonlinearity in dye-doped nematic liquid crystals[J].Opt.Lett.,1998,23:253-255
[117]蒋建伟.表面增强拉曼散射在研究几种偶氮染料分子吸附特性中的应用[D],开封:河南大学,2005
[118]Kuwabara T,Nakajima H,Nanasawa M,et al.Color change indicators for molecules using methyl red-modified cyclodextrins[J].Anal.Chem.,1999,71:2844-2849
[119]Reilley C N,Smith E M.Chemical application of complementary tristimulus colorimetry[J].Anal.Chem.,1960,32(10):1233-1240
[120]Ramette R W,Dratz E A,Kelly P W.Acid-base equilibria of methyl red[J].J.Phys.Chem.,1962,66(3):527-532
[121]Seu G.Spectrophotometric study of the prototropic equilibrium of methyl red in organic solvent[J].Dyes Pigments,1995,29(3):227-240
[122]周公度,段连运.结构化学基础[M].第四版.北京:北京大学出版社,2008:324
[123]刘灵燕.酸性橙Ⅱ水滑石插层结构的实验与理论研究[D].北京:北京化工大学,2008