摘要
第一章卤键是发生在卤素原子(路易斯酸)与中型或阴离子路易斯碱之间的一种非共价弱相互作用力,本章主要对卤键发展的历史与现状及主要特征进行了综述,并突出其与氢键的相似性,介绍了基于卤键晶体工程发展中的一些启示性原理,焦点集中于卤碳的卤键超分子体系,显示了卤键在合成化学、材料科学、化学传感与分子识别及生物有机化学领域的应用潜力。
第二章在HF/6-31(d)水平上对气相中的CBr4/甲醇、乙醇、乙醚、四氢呋喃、二氧六环的单体和配合物的构型进行优化得到了配合物的键长、键角、相互作用能等参数,键长位于范得华半径之内表明Br…O间的卤键弱相互作用力的存在。对四溴化碳溶于甲醇、乙醇、丙酮、四氢呋喃等含氧孤电子对有机溶剂的光电性能的研究表明:当浓度超过7.8×10~(-3)M~1.6×10~(-2)M的临界浓度范围时,高浓度依赖性的卤键特殊溶剂效应与最高浓度的一般溶剂效应共存,相反地,当浓度低于此临界浓度范围时,溶液中仅存在一般溶剂效应。卤键供/受体间的电荷转移(CT)相互作用如同氢键一样导致了光谱的红移,其中,电荷转移配合物的紫外-可见吸收光谱在丙酮溶剂中易于辨认,而其它五个溶剂的光谱则必须通过特殊溶剂效应曲线减去最高浓度的一般溶剂效应曲线才能得到。适合二组分体系的Benesi-Hildebrand方程证实了四溴化碳与各种溶剂间形成丁1:1的配合物。四溴化碳溶解在甲醇、乙醇、丙酮、四氢呋喃中的氧化电位与相应的吸收能量的线性关系建立了CBr4/溶剂的高浓度依赖性的电荷转移性能间的关系。试验过程中发现:环境光辐射使四溴化碳脱溴从而导致了350~390nm范围内的光谱拖尾。
第三章得到了DPY/5-Isal和Py/DIF_4B分子间自组装晶体,单晶衍射结果表明:前者以5-碘水杨酸分子间的C-I...O(羰基)卤键作为两侧“梯柱”,两侧“梯柱”羧酸上的羟基与4,4-二吡啶以氢键结合形成“梯梁”的“梯”状晶体;后者是由两个Py分子中包含两个碘反向的DIF_4B分子的“夹心”柱状无限链结构,Py及DIF_4B间以π-π堆积为驱动力,柱状链间则通过I…I作用连接。研究表明卤键与氢键及π-π堆积等弱作用间的协同作用对人类生命起源的认识、药物设计及生物体内分子间识别具有重大的意义。
第四章本文报道了1,2-2(4-吡啶)乙烯(BPE)随pH变化的光谱特性。当pH值从7.20减少到-1.0时,紫外-可见吸收以及荧光光谱在四个不同的连续的pH区间8.45~7.20,7.20~5.62,5.62~2.60,2.60~-1.0呈现相同的变化趋势。即不变,减弱,增强,再减弱。其中,在7.20~5.62的范围内,紫外-可见吸收波长由298nm红移到313nm,荧光发射由418nm蓝移到359nm;当pH2.60低到-1.0左右,阳离子-π作用降低了π电子云密度使荧光强度减弱直至猝灭。通过拟合得到两级解离常数pKa_1=4.30±0.01和pKa_2=5.65±0.04,光谱变化显示:该化合物按pH值由高到低显示了“关-开-关”的荧光发射性能,可应用于荧光分子开关,同时又是一个较好的pH探针。α-,β-环糊精的存在对光谱几乎无影响。
Chapter 1 Halogen bonding is the noncovalent interaction between halogen atoms(Lewis acids) and neutral or anionic Lewis bases.History,current situation and main features of the interaction were given,and the close similarity with the hydrogen bonding became apparent.Some heuristic principles are presented to develop a rational crystal engineering based on halogen bonding.The focus was on halogen-bonded supramolecular architect- tures given by halocarbons.The potential of the interaction was shown by useful applications in the field of synthetic chemistry,material science,chemical sensing and molecular recognition,bioorganic chemistry.
Chapter 2 The data about geometries and interaction energies for the carbon tetrabromide complexes with methanol,ethanol,dioxane,dietyl ether, tetrahydrofuran using ab initio methods were obtained.C-Br…O distances are within the van der Waals radius sum,which revealed the existence of the weak halogen bonding interaction between Bromine and Oxygen atoms.The photoelectrical characters of carbon tetrabromide(CBr_4) dissolved in methanol,ethanol,acetone,dioxane,dietyl ether,tetrahydrofuran were investigated.High concentration-dependent halogen bonding(XB) specific solvent effect co-existed with the highest concentration general solvent effect when concentration of CBr_4 was over 7.8×10~(-3)M~1.6×10~(-2)M critical concentration range,in contrary,below this concentration range only did general solvent effect occur.Charge-transfer(CT) interaction between halogen bonding donor-acceptor resulted in spectral red-shift as hydrogen bonding (HB).Among these,UV-Vis spectrum of specific solvent effect was resolved easily in acetone,as for other five solvents,only could by spectral digital subtractions of the critical concentration absorption of CBr_4 from the spectra of solutions containing both reagents obtain the distinct spectra of specific solvent effect due to the spectra overlaping between the highest concentration general solvent effect and specific one.1:1 complexes formed were testified by modified Benesi - Hildebrand equation.The linear correlation of anodic potentials with the spectral energies of four organic solvents complexes established the high concentration-dependent charge-transfer character of the CBr_4/solvent associations.Ambient light made CBr_4 disassociate bromine which lead to spectral tail in the range of 350~390nm.
Chapter 3 In this chapter the intermolecular crystals self-aggregated by DPY/5-Isal and Py /DIF_4B were obtained,respectively.The results from single crystal diffraction indicated:The former was ladder-like crystal with the feature of both bilateral "ladder columns" constructed by the C-I…O (carbonyl) halogen-bonding from 5-Isal molecules and "ladder girder" did by hydroxide from carboxylic group and nitrogen from 4,4-Bipyridyl.The latter was "sandwiched column-like" infinite chain containing two DIF_4B molecules with reverse iodine between two Py molecules,π-πstacking drove the self-aggregation of Py and DIF_4B molecules,but the two neighboring columns were connected by I…I interaction.Synergetically interaction by halogen-bonding with hydrogen-bonding,π-πstacking and other weak interactions had great meaning for the understanding for life initiation, medical design and intermolecular recognition in biological bodies.
Chapter 4 With decrease ofpH from 7.20 to-1.0,the UV-Vis absorption and fluorescent spectra of the 1,2-bis(4-pyridyl) ethylene(BPE) took on same changing trends at four different successive pH stages:8.45~7.20,7.20~5.62, 5.62~2.60,2.60~-1.0,namely corresponding to no change,decrease,increase, decrease again.Among these,at the range of 7.20~5.62,the wavelength of fluorescence blueshifted from 418nm to 359nm,but that of UV-Vis,in contrast,redshifted from 285nm to 298nm.Fluorescence had a drop even to quench upon pH from 2.60 to -1.0 due to its cation-πinteraction to reduceπelectron cloud density of BPE Two dissociation constants,pKa_1 4.30±0.01 and pKa2 5.65±0.04,were obtained based on fluorescence data.The changes of spectra indicated that BPE had "off-on-off' fluorescence emission behavior.The spectra of BPE were nearly independent on the presence ofαandβ-cyclodextrins.
引文
[1]Guo W.Z.,Galoppini E.,Gilardi R.,Weak Intermolecular Interactions in the Crystal Structures of Molecules with Tetrahedral Symmetry:Diamondoid Nets and Other Motifs.Cryst.Growth.Des.,2001,1,231-237.
[2]Mons M.,Dimicoli I.,Tardivel B.,Piuzzi F.,Brenner V.,Millie P.,Site Dependence of the Binding Energy of Water to Indole:Microscopic Approach to the Side Chain Hydration of Tryptophan.J.Phys.Chem.A,1999,103,9958-9965.
[3]Kui,S.C.F.,Chui S.S.Y.,Che C.M.,Zhu N.Y.,Structures,Photoluminescence.and Reversible Vapoluminescence Properties of Neutral Platinum(Ⅱ) Complexes Containing Extended(?)-Conjugated Cyclometalated Ligands.J.Am.Chem.Soc.,2006,128,8297-8309.
[4]Bent H A.,Structural chemistry of donor-acceptor interactions.Chem.Rev.,1968,68,587-648.
[5]Lommerse J.P.M.,Stone A.J.,Taylor R.,Allen,F.H.,The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen,J.Am.Chem.Soc.,1996,118,3108-3116.
[6]Desiraju G.R.,Harlow R.,Cyano-halogen interactions and their role in the crystal structures of the 4-halobenzonitriles.J.Am.Chem.Soc.,1989,111,6757- 6764.
[7]Caronna T.,Liantonio R.,Logothetis T.A.,Metrangolo E,Halogen Bonding and π…π.Stacking Control Reactivity in the Solid State.J.Am.Chem.Soc.,2004,126,4500-4501.
[8]Amico V.,Meille S.V.,Corradi E.,Messina M.T.,Resnati G.,Perfluorocarbon-Hydrocarbon Self-Assembling.1D Infinite Chain Formation Driven by Nitrogen…Iodine Interactions.J.Am.Chem.Soc.1998,120,8261- 8262.
[9]Manfredi A.,Messina M.T.,Metrangolo P.,Pilati T.,Quici S.,Resnati G.,Design and Synthesis of New Tectons for Halogen Bonding-driven Crystal Engineering.Supramol.Chem.,2000,12,405-410.
[10]Ouvrard C.,Le Questel J.Y.,Berthetot M.,Laurence C.,Halogen-bond geometry:a crystallographic database investigation of dihalogen complexes.Acta,Crystallogr.,B,2003,B59,512-526.
[11]Cheetham N.F.,Pullin A.D.E.,A gas-phase donor-acceptor complex.Chem.Commun.,1967,233-234.
[12]Legon A.C.,π-Electron "Donor-Acceptor" Complexes B…ClF and the Existence of the "Chlorine Bond".Chem.Eur.J.,1998,4,1890-1897.
[13]Legon A.C.,Prereactive Complexes of Dihalogens XY with Lewis Bases B in the Gas Phase:A Systematic Case for the Halogen Analogue B…XY of the Hydrogen Bond B…HX.Angew.Chem.Int.Ed.,1999,38,2686-2714.
[14]Wash P.L.,Ma S.,Obst U.,Rebek J.Nitrogen-Halogen Intermolecular Forces in Solution.J.Am.,Chem.Soc.,1999,121,7973-7974.
[15] Chu . L., Wang Z.M., Huang Q. C., Yan C. H., Zhu S. Z., Fluorine-Containing Donor-Acceptor Complex: Infinite Chain Formed by Oxygen-Iodine Interaction. J. Am. Chem. Soc, 2001. 123, 11069-11070.
[16] Zou J. W., Jiang Y. J., Guo M., Hu G. X., Zhang B., Liu H. C., Yu Q S. Ab Initio Study of the Complexes of Halogen-Containing Molecules RX (X=Cl, Br, and I) and NH_3: Towards Understanding the Nature of Halogen Bonding and the Electron-Accepting Propensities of Covalently Bonded Halogen Atoms. Chem. Eur. J, 2005, 11, 740-745.
[17] Auffinger P., Hays F. A., Westhof E., Ho P. S., Halogen bonds in biological molecules. PNAS, 2004, 101, 16789-16794.
[18] Metrangolo P., Neukirch H., Pilati T., Resnati G., Halogen Bonding Based Recognition Processes: A World Parallel to Hydrogen Bonding. Acc. Chem. Res., 2005, 38, 386-395.
[19] Wang Y. H., Zou J. W., Lu Y. X., Yu H. Y., Theoretical investigation on charge-assisted halogen bonding interactions in the complexes of bromocarbons with some anions. Int. J. Quan. Chem., 2007, 107, 501-506.
[20] Wei H. Q., Jin W. J., Halogen bonding: a new non-covalent interaction for driving intermolecular recognition processes. Chinese J. Anal. Chem., 2007,35, 1381-1386.
[21] Metrangolo P., Resnati G., Palati T., Liantonio R., Meyer F., Engineering functional materials by halogen bonding. J. Polym. Sci. A, 2007, 45, 1-15.
[22] Benesi H. A., Hildebrand J. H., ULTRAVIOLET ABSORPTION BANDS OF IODINE IN AROMATIC HYDROCARBONS. J. Am. Chem. Soc, 1948, 70, 2832-2833.
[23] Hassel O., Hvoslef J., Structure of compound between 1.4-dioxane and inorganic substances. Acta. Chem. Scand., 1954, 8, 873-873.
[24] Hassel O., Romming C., Direct structural evidence for weak charge-transfer bonds containing chemically saturated molecules. Quart. Rev. Chem. Soc, 1962, 16, 1-18.
[25] Hassel O., Structural aspects of interatomic charge-transfer bonding. Science, 1970, 170,497-502.
[26] Dumas J. M., Gomel M., Guerin M., Molecular Interaction Involving Organic Halides, New York, 1983, Chapter 21, PP985-2714.
[27] Legon A. C, Waclawik E. R., Real-time vibrational mode-coupling associated with ultrafast geometrical relaxation in polydiacetylene induced by sub-5-fs pulses. Chem. Phys. Lett, 1999,321,385-393.
[28]Metrangolo P.,Resnati G.,Halogen Bonding:A Paradigm in Supramolecular Chemistry.Chem.Eur.J.,2001,7,2511-2519.
[29]Sakurai T.,Sundaralinga M.,Jeffrey G.A.,A nuclear quadrupole resonance and X-ray study of the crystal structure of 2,5-dichloroaniline.Acta Crystallogr.,1963,16.354-363.
[30]Stone A.J.,Lucas J.,Rowland R.S.,Thomley A.E.,The Nature of-Cl.cntdot.,cntdot..cntdot,el-Intermolecular Interactions.J.Am.Chem.Soc.,1994,116,4910-4918.
[31]Corradi E.,Meille S.V.,Messina M.T.,Metrangolo P.,Resnati G.,Perfluorocarbon-hydrocarbon self-assembly.Part 6:~1,ω-Diiodoperfluoro- alkanes as pseudohalogens in supramolecular synthesis.Tetrahedron Lett.,1999,40(42):7519-7523.
[32]Awwadi F.F.,Willett R.D.,Peterson K.A.,Twamley B.,The Nature of Halogen…Halogen Synthons:Crystallographic and Theoretical Studies.Chem.Eur.J.,2006,12,8952-8956.
[33]Metrangolo P.,Pilatib T.,Resnati G.,Halogen bonding and other noncovalent interactions involving halogens:a terminology issue.CrystEngComm,2006,8,946-947.
[34]Desiraju G.R.,Parthasarathy R.,The nature of halogen.cntdot..cntdot..cntdot.halogen interactions:are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms?.J.Am.Chem.Soc.,1989,111,8725-8726.
[35]Politzer P.,Lane P.,Concha M.C.,Ma Y.G.,Murray J.S.,Theoretical investigation on charge-assisted halogen bonding interactions in the complexes of bromocarbons with some anions.J.Mol.Model.,2007,13,305-311.
[36]Clark T.,Hennemann M.,Murray J.S.,Politzer P.,Halogen bonding:the -hole.J.Mol.Model.,2007,13,291-296.
[37]Ramasubbu N.,Parthasarathy R.,Murray-Rust P.,Angular preferences of intermolecular forces around halogen centers:preferred directions of approach of electrophiles and nucleophiles around carbon-halogen bond.J.Am.Chem.Soc.,1986,108,4308-4314.
[38]Saha B.K.,Nangia A.,Nicoud J.F.,Using Halogen…Halogen Interactions to Direct Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules.Cryst.Growth.Des.,2006,6,1278-1281.
[39]Bosch E.,Barnes C.L.,Triangular Halogen-Halogen-Halogen Interactions as a Cohesive Force in the Structures of Trihalomesitylenes.Cryst.Growth.Des.,2002,2,299-302.
[40] Corradi E., Meille S. V., Messina M. T., Metrangolo P., Resnati G., Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes. Angew. Chem. Int. Ed., 2000,39,1782-1786.
[41] Metrangolo P., Resnati G., Halogen bonding, in: Encyclopedia of Supramolecular Chemistry, Marcel Dekker, 2004, 628-635.
[42] Santis A. D., Forni A., Liantoni R., Metrangolo P., Pilati T., Resnati G., N…Br Halogen Bonding: One-Dimensional Infinite Chains through the Self-Assembly of Dibromotetrafluorobenzenes with Dipyridyl Derivatives. Chem. Eur. J., 2003, 9, 3974.3974.
[43] Pilati T., Metrangolo P., Proserpio D., Resnati G., A nuclear quadrupole resonance and X-ray study of the crystal structure of 2,5-dichloroaniline. Acta Crystallogr., 2005, A61, C363-372.
[44] Liang W. J., Wang Y., Feng F., Jin W. J., Novel self-protective phosphorescence from crystalline nanoparticles assembled by 3-bromo- and 3-iodo-carbazoles based on halogen-halogen interaction in suspension solutions. Anal. Chim. Acta, 2006, 572. 295-302.
[45] Grineva O. V., Zorkii P. M., Isostructural and nonisostructural compounds in series organic crystal substances: Structure of hal-aggregates. J. Struc. Chem., 2001, 42, 16-23.
[46] Pople J. A., Head-Gordon M., Raghavachari K., et al., Quadratic Configuration Interaction, A General Technique for Determining Electron Correlation Energies. J. Chem. Phys. 1987, 87, 5968-5975.
[47] Moller C., Plesset M. S., Note on an Approximation Treatment for Many-Electron Systems. Phys. Rev,. 1934, 46, 618-622.
[48] Pople J. A., Binkley R., Seeger R., Theoretical Models Incorporating Electron Correlation. Int. J. Quant. Chem. Symp., 1976, 10, 1-19.
[49] Krishnan R., Pople J. A., Appoximate Forth-Order Perturbation Theory of the Electron Correlation Energy. Int. J. Quantum. Chem., 1978, 14, 91-100.
[50] Hohenberg P., Kohn W., Inhomogeneous Electron Gas. Phys. Rev., 1964, 136, B864-B871.
[51] Kohn W., Sham L. J., Self-Consistent Equations Including Exchange and Correlation Effects. Phys. Rev., 1965, 140, A1133-A1138.
[52] Slater J. C., Quantum Theory of Molecular and Solids. Vol. 4: The Self-Consistent Field for Molecular and Solids McGraw-Hill: New York, 1974.
[53] Salahub D. R., Zerner M. C., The Challenge of d and f Electrons ACS: Washington. D.C., 1989.
[54] Parr R. G., Yang W., Density-Functional Theory of Atoms and Molecules. Oxford Univ. Press: Oxford, 1989.
[55] Lommerse J. P. M., Stone A. J., Taylor R., Allen F. H., The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen. J. Am. Chem. Soc, 1996, 118,3108-3116.
[56] Glaser R., Chen N. J., Wu H., Knotts N., Kaupp M.,~(13)C NMR Study of Halogen Bonding of Haloarenes: Measurements of Solvent Effects and Theoretical Analysis. J. Am. Chem. Soc, 2004. 126,4412-4419.
[57] Riley K. E., Merz K. M., Jr., Insights into the Strength and Origin of Halogen Bonding: The Halobenzene-Formaldehyde Dimer. J. Phys. Chem. A, 2007, 111, 1688-1694.
[58] Valerio G., Raos G., Meille S. V., Metrangolo P., Reanati G., Halogen Bonding in Fluoroalkylhalides: A Quantum Chemical Study of Increasing Fluorine Substitution. J. Phys. Chem., A, 2000, 104,1617-1620.
[59] Reley K. E., Hobza P., Investigations into the Nature of Halogen Bonding Including Symmetry Adapted Perturbation Theory Analyses. J. Chem. Theory Comput., 2008,4,232-242.
[60] Grabowski S. J., Bilewicz E., Cooperativity halogen bonding effect - Ab initio calculations on H_2CO...(ClF)_n complexes. Chem. Phys. Lett., 2006, 427, 51-55.
[61] Wu J. Y., Zhang J. C., Cao W. L., Theoretical study on intermolecular interactions in BrF/H_nX adducts. Chem. Phys., 2007, 338, 69-74.
[62] Cheng W. D., Shen J., Wu D. S., Li X. D., Lan Y. Z., Li F. F., Huang S. P., Zhang H., Gong Y. J., Electronic Origin for Enhanced Nonlinear Optical Response of Complexes from Tetraalkylammonium Halide and Carbon Tetrabromide: Electrostatic Potentials of Intermolecular Donor-Acceptor Dyads. Chem. Eur. J., 2002, 12, 6880-6887.
[63] Wang W. Z., Wong N. B., Zheng W. X., Tian A., Matrix-Isolation in Cryogenic Water-Ices: Facile Generation, Storage, and Optical Spectroscopy of Aromatic Radical Cations. J. Phys. Chem., A, 2004, 108, 4412-4419.
[64] Lu Y. X., Zou J. W., Wang Y. H., Yu Q. S., Theoretical investigations of the C-X/π interactions between benzene and some model halocarbons. Chem. Phys., 2007, 334, 1-7.
[65] Shi Q. C, Lu Y. X., Fan J. C., Zou J. W., Wang Y. H., Understanding the magnitude and origin of bidentate charge-assisted halogen bonds of halo-perfluorocarbons and halo-hydrocarbons with halide anions. J. Mol. Struct., THEOCHEM., 2008, 853, 39-44.
[66] Tawarada R., Seio K., Sekine M., Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons: Investigation of Possible Halogen Bonding Base Pairs. J. Org. Chem., 2008, 73, 383-390.
[67] Corradi E., Meile S. V., Messina M. T., Metrangolo P., Resnati G., Perfluorocarbon- hydrocarbon self-assembly. Part 6:~1 *,ω-Diiodoperfluoro- alkanes as pseudohalogens in supramolecular synthesis. Tetrahedron Lett., 1999, 40, 7519-7523.
[68] Walsh R. B., Padgett C. W., Metrangolo P., esnatiG. R, Hanks T. W., Pennington W. T., Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides. Cryst. Growth. Des., 2001, 1, 165-175.
[69] Santis A. D., Forni A., Liantonio R., Metrangolo P., Pilati T., Resnati G., N…Br Halogen Bonding: One-Dimensional Infinite Chains through the Self-Assembly of Dibromotetrafluorobenzenes with Dipyridyl Derivatives. Chem. Eur. J., 2003, 9, 3974-3983.
[70] Bailey R. D., Hook L. L., Watson R. P., Hanks T. W., Pennington W. T., Tetraiodoethylene: a supramolecular host for Lewis base donors. Cryst. Engineering, 2000, 3,155-171.
[71] Corradi E., Meille S. V., Messina M. T., Metrangolo P., Resnati G., Halogen Bonding versus Hydrogen Bonding in Driving Self-Assembly Processes. Angew. Chem. Int. Ed., 2000,39,1782-1786.
[72] Messina M. T., Metrangolo P., Pappalardo S., Parisi M. F., Pilati T., Resnati G., Perfluorocarbon-Hydrocarbon Self-Assembly: Part X Interactions at the Outside Faces of Calix[4]arenes: Two-Dimensional Infinite Network Formation with Perfluoroarenes. Chem. Eur. J., 2000, 6, 3495-3500.
[73] Crihfield A., Hartwell J., Phelps D., Walsh R. B., Harris J. L., Payn e J. F., Pennington W. T., Hanks T. W., Crystal Engineering through Halogen Bonding. 2. Complexes of Diacetylene- Linked Heterocycles with Organic Iodides. Cryst. Growth. Des., 2003, 3, 313-320.
[74] Liantonio R., Metrangolo P., Pilati T., Resnati G., Sternazzi A., Perfluorocarbon- Hydrocarbon Self-Assembly:First Crystalline Halogen-Bonded Complex Involving Bromoperfluoroalkanes.Cryst.Growth.Des.,2003,3,799-803.
[75]Lunghi A.,Cardillo P.,Messina T.,Metrangolo P.,Panzeri W.,Resnati G.,Perfluorocarbon-hydrocarbon self assembling.Thermal and vibrational analyses of one-dimensional networks formed by *,ω-diiodoperfluoroalkanes with K.2.2.and K.2.2.2.J.Fluo.Chem.,1998,91,191-194.
[76]Liantonio R.,Metrangolo P.,PilatT.i,Resnati G.,Fluorous Interpenetrated Layers in a Three-Component Crystal Matrix.Cryst.Growth.Des.,2003,3,355-361.
[77]Walsikwska A.,Gdaniec M.,Polonski T.,Co-crystals of iodopentafluorobenzene with nitrogen donors:2-Dmolecular assemblies through halogen bonding and arylperfluoroaryl interactions.CryEngComm,2007,9,203-206.
[78]Zhu S.Z.,Xing C.X.,Xu W.,Jin G.F.,Li Z.T.,Halogen Bonding and Hydrogen Bonding Coexist in Driving Self-Assembly Process.Cryst.Growth.Des.,2004,4,53-56.
[79]GoroffN.S.,Curtis S.M.,Webb J.A.,Fowler F.W.,Lauher J.W.,Designed Cocrystals Based on the Pyridine-Iodoalkyne Halogen Bond.Org.Lett.,2005,7,1891-1893.
[80]Bouchmella K.,Boury B.,Dutremez S.G.,A.van der Lee,Molecular Assemblies from Imidazolyl-Containing Haloalkenes and Haloalkynes:Competition between Halogen and Hydrogen Bonding.Chem.Eur.J.,2007,13,6130-6138.
[81]Pigge F.C.,Vangala V.R.,Swenson D.C.,Relative importance of X...OLC vs.X...X halogen bonding as structural determinants in 4-halotriaroylbenzenes.Chem.Commun.,2006,2123-2125.
[82]Kubicki M.,Crystal packing modes of 1-(4'-aryl)-4-nitro-5-methylimidazoles:π-stacking,weak hydrogen bonds and C-Cl...O halogen bonds.J.Mol.Struct.,2004,698.67-73.
[83]Li W.,Rasmussen S.C.,Synthesis and structural characterization of 2,5-dihalo-3,4-dinitrothiophenes.J.Chem.Crastallogr.,2007,37,387-398.
[84]Adams C.J.,Bowen L.E.,I.π halogen-bonding in the structures of platinumalkynyl compounds:an overlooked supramolecular interaction.J Chem.Soc.Dalton Trans.,2005,2239-2240.
[85]Zordan F.,Brammer L.,Sherwood P.,Supramolecular Chemistry of Halogens:Complementary Features of Inorganic(M-X) and Organic(C-X') Halogens Applied to M-X...X'-C Halogen Bond Formation.J.Am.Chem.Soc.,2005,127,5979-5989.
[86]Zordan F.,Brammer L.,M-X...X'-C Halogen-Bonded Network Formation in MX2(4-halopyridine)_2 Complexes(M = Pd,Pt;X = C1,2;X' = C1,Br,I).Cryst.Growth.Des.,2006,6,1374-1379.
[87]Brammer L.,Espallargas G.M.,Adams H.,Involving metals in halogen-halogen interactions:second-sphere Lewis acid ligands for perhalometallate ions(M-X...X'-C).CrystEngComm,2003,343-345.
[88]Britton D.,4,4'-Diiodobiphenyl.Acta Cryst.E61,2005,O187-O188.
[89]Freytag M.,Jones R G.,Ahrens B.,Fischer A.K.,Hydrogen bonding and halogen -halogen interactions in 4-halopyridinium halides.New.J.Chem.,1999,1137-1139.
[90]Bosch E.,Barnes C.L.,Triangular Halogen-Halogen-Halogen Interactions as a Cohesive Force in the Structures of Trihalomesitylenes.Cryst.Growth Des.,2002,2,299-302.
[91]Reddy C.M.,Kirchner M.T.,Gundakaram R.C.,Padmanabhan K.A.,Desiraju G.R.,Isostructurality,Polymorphism and Mechanical Properties of Some Hexahalogenated Benzenes:The Nature of Halogen...Halogen Interactions.Chem.Eur.J.,2006,12,2222-2234.
[92]LiebermaH.F.n,Davey R.J.,Newsham D.M.,Br...Br and Br...H Interactions in Action:Polymorphism,Hopping,and Twinning in 1,2,4,5-Tetrabromobenzene.Chem.Mater,2000,12,490-494.
[93]Lucassen A.C.B.,Karton A.,Leitus G.,Shimon L.J.W.,Martin J.M.L.,M.E.van der Boom,Co-Crystallization of Sym-Triiodo-Trifluorobenzene with Bipyridyl Donors:Consistent Formation of Two Instead of Anticipated Three N...I Halogen Bonds.Cryst.Growth Des.,2007,7,386-392.
[94]Bertani R.,Metrangolo P.,Moiana A.,Perez E.,Pilati T.,Resnati G.,Rico-Lattes I.,Sassi A.,Supramolecular Route to Fluorinated Coatings:Self-Assembly Between Poly(4-vinylpyridines) and Haloperfluorocarbons.Adv.Mater,2002,14,1197-1201.
[95]Ngugen H.L.,Horton P.N.,Hursthouse M.B.,Legon A.C.,Bruce D.W.,Halogen Bonding:A New Interaction for Liquid Crystal Formation.J.Am.Chem.Soc.,2004,126,16-17.
[96]Metrangolo P.,Prasan C.g,Resnati G.,Liantonio R.,Withwood A.C.,Bruce D.W.,Fluorinated liquid crystals formed by halogen bonding.Chem.Commun.,2006, 3290-3292.
[97]Xu J.W.,Liu X.M.,J.Kok-Peng Ng,Lin Y.T.,He C.B.,Trimeric supramolecular liquid crystals induced by halogen bonds.J.Mater.Chem.,2006,3540-3545.
[98]Xu J.W.,Liu X.M.,Lin T.T.,Huang J.C.,He C.B.,Synthesis and Self-Assembly of Difunctional Halogen-Bonding Molecules:A New Family of Supramolecular Liquid-Crystalline Polymers.Macromolecules,2005,38,3554-3557.
[99]Forni A.,Metrangolo P.,Pilati T.,Resnati G.,Halogen Bond Distance as a Function of Temperature.Cryst.Growth Des.,2004,4,291-295.
[100]Jean-Laurent Syssa-Magale,Boubekeur K.,Palvadeau P.,Meerschaut A.,Schollhorn B.,Self-assembly via(N...I) non-covalent bonds between 1,4- diiodo-tetrafluoro-benzene and a tetra-imino ferrocenophane.J.Mol.Struct.,2004,691,79-84.
[101]Cariati E.,Forni A.,Biella S.,Metrangolo R,Meyer F.,Resnati G.,Righetto S.,Tordin E.,Ugo R.,Tuning second-order NLO responses through halogen bonding.Chem.Commun.,2007,2590-2592.
[102]Wang F.,Ma N.,Chen Q.X.,Wang W.B.,Wang L.Y.,Halogen Bonding as a New Driving Force for Layer-by-Layer Assembly.Langmuir,2007,23,9540-9542.
[103]Tanaka K.,Fujimoto D.,Altreuther A.,Oeser T.,Irngartinger H.,Toda F.,Chiral inclusion crystallization of achiral tetrakis(p-halophenyl)- ethylenes with achiral guest compounds.J.Chem.Soc.,Perkin Trans.2,2000,2115-2120.
[104]Tanaka K.,Fujimoto D.,Oeser T.,Irngartinger H.,Toda F.,Chiral inclusion crystallization of tetra(p-bromophenyl)ethylene by exposure to the vapor of achiral guest molecules:a novel racemic-to-chiral transformation through gas-solid reaction.Chem.Commun.,2000,413-414.
[105]Farina A.,Meille S.V.,Messina M.T.,Metrangolo P.,Resnati G.,Vecchio G.,Resolution of Racemic 1,2-Dibromohexafluoropropane through Halogen-Bonded Supramolecular Helices.Angew.Chem.Int.Ed.,1999,38,2433-2436.
[106]Farina A.,Meille S.V.,Messina M.T.,Metrangolo P.,Resnati G.,(-)-Sparteinium bromide.Acta Crystallogr.,1999,C55,1710-1711.
[107]Neukirch H.,Guido E.,Liantonio R.,Metrangolo P.,Pilati T.,Resnati G.,Spontaneous resolution in a halogen bonded supramolecular architecture.Chem.Commun.,2005,1534-1536.
[108] Boubekeur K., Syssa-Magal J. L., Palvadeau P., Schllhorn B., Self-assembly of nitroxide radicals via halogen bonding—directional NO~·…I interactions. Tetrahedron Lett., 2006, 47, 1249-1252.
[109] Metrangolo P., Panzeri W., Recupero F., Resnati G., Perfluorocarbon- hydrocarbon self-assembly Part 16. ~(19)F NMR study of the halogen bonding between halo-perfluoro- carbons and heteroatom containing hydrocarbons. J. Fluo. Chem., 2002, 114, 27-33.
[110] Takeuchi T., Minato Y. J., Takase M., Shinmori H., Molecularly imprinted polymers with halogen bonding-based molecular recognition sites. Tetrahedron Lett., 2005, 46, 9025-9027.
[111] Mele A., Metrangolo P., Neukirch H., Pilati T., Resnati G., A Halogen-Bonding-Based Heteroditopic Receptor for Alkali Metal Halides. J. Am. Chem. Soc, 2005, 127, 14972-14973.
[112] Gattuso G., Liantonio R., Metrangolo P., Meyer F., Resnati G., Pappalardo A., Parisi M. F., Pilati T., PisagattI. i, Hybrid calixarene/inorganic salt/diiodoperfluorocarbon supramolecular assemblies. Supramol. Chem., 2006, 18, 235-243.
[113] Casnati A., Liantonio R., Metrangolo P., Rasnati G., Ungaro R., Ugozzoli F.. Molecular and Supramolecular Homochirality: Enantiopure Perfluorocarbon Rotamers and Halogen-Bonded Fluorous Double Helices. Angew. Chem. Int. Ed., 2006, 45, 1915-1918.
[114] Caronna T., Liantonio R., Logothetis T. A., Metrangolo P., Pilati T., Resnati G., Halogen Bonding and π…π Stacking Control Reactivity in the Solid State. J. Am. Chem. Soc, 2004, 126,4500-4501.
[115] Marras G., Metrangolo P., Meyer F., Pilati T., Resnati G., Vij A., Solid state synthesis under supramolecular control of a 2D heterotetratopic self-complementary tecton tailored to halogen bonding. New J. Chem., 2006, 1397-1402.
[116] Wojtczak A., Cody V., Luft J. R., Pangborn W., Structure of rat transthyretin (rTTR) complex with thyroxine at 2.5AE resolution: first non-biased insight into thyroxine binding reveals different hormone orientation in two binding sites. Acta Crystallogr, D, 2001,57, 1061-1070.
[117] Steinrauf L. K., Hamilton J. L., Braden B. C, X-ray Crystal Structure of the Ala-109 I) Thr Variant of Human Transthyretin Which Produces Euthyroid Hyperthyroxinem. J. Biol.Chem.,1993,268,2425-2430.
[118]Van Pee K.H.,Unversucht S.,Biological dehalogenation and halogenation reactic,ns.Chemosphere,2003,52,299-312.
[119]Buss I.H.,Senthilmohan R.,Darlow B.A.,3-Chlorotyrosine as a marker of protein damage by myeloperoxidase in tracheal aspirates from preterm infants:association with adverse respiratory outcome.Pediatr.Res.,2003,53,455-462.
[120]Wu W.J.,Samoszuk M.K.,Comhair S.A.,Eosinophils generate brominating oxidants in allergen-induced asthma.J.Clin.Invest.,2000,105,1455-1463.
[121]Shen Z.,Mitra S.N.,Wu W.,Chen Y.,Yang Y.,Qin J.,Hazen S.L.,Eosinophil Peroxidase Catalyzes Bromination of Free Nucleosides and Double-Stranded DNA.Biochem.,2001,40,2041-2051.
[122]Vargason J.M.,Eichman B.F.,Ho R S.,The extended and eccentric E-DNA structure induced by cytosine methylation or bromination.Nat.&ruct.Biol.,2000,7,758-761.
[123]Voth A.R.,Hays F.A.,Ho P.S.,Directing macromolecular conformation through halogen bonds.PNAS,2007,104,6188-6193.
[124]Jiang Y.,Alcaraz A.A.,Chen J.M.,Kobayshi H.,Lu Y.J.,Snyder J.R,Diastereomers of Dibromo-7-epi-10-deacetylcephalomannine:Crowded and Cytotoxic Taxanes Exhibit Halogen Bonds.J.Med.Chem.,2006,49,1891-1899.
[125]Gopalakrishana B.,Aparna V.,Jeevan J.,A Virtual Screening Approach for Thymidine Monophosphate Kinase Inhibitors as Antitubercular Agents Based on Docking and Pharmacophore Models.J.Chem.Inf.Model,2005,45,1101-1108.
[1]Legon A.C.,π-Electron "Donor-Acceptor" Complexes B-ClF and the Existence of the "Chlorine Bond".Chem.Eur.J.,1998,4,1890-1897.
[2]Legon A.C.,Prereactive Complexes of Dihalogens XY with Lewis Bases B in the Gas Phase:A Systematic Case for the Halogen Analogue B...XY of the Hydrogen Bond B.--HX.Angew.Chem.Int.Ed.,1999,38,2686-2714.
[3]Metrangolo P.,Neukirch H.,Pilati T.,Resnati G.,Halogen Bonding Based Recognition Processes:A World Parallel to Hydrogen Bonding.Acc.Chem.Res.,2005,38,386-395.
[4]Wei H.Q.,Jin W.Application of halogen bonding in chemical sensing and molecular recognition.Chinese J.Anal.Chem.,2007,35,1381-1386.
[5]Metrangolo P.,Resnati G.,Palati T.,Liantonio R.,Meyer F.,Engineering functional materials by halogen bonding.J.Polym.Sci.A,2007,45,1-15.
[6]Lucassen A.C.B.,Vartanian M.,LeituG.S.,M.E.Van der Boom,4'-Bromo-2',3',5',6'-tetrafluorostilbazole:Donor and Acceptor Site for Halogen Bonding and π-Stacking in One Rigid-Rod-Type Molecule.Cryst.Growth.Des.,2005,5,1671-1673.
[7]Metrangolo R,Meyer E,Pilati T.,Proserpio D.M.,Resnati G,Highly Interpenetrated Supramolecular Networks Supported by N...I Halogen Bonding.Chem.Eur J.,2007,13,5765-5772.
[8]Walsikwska A.,Gdaniec M.,Polonski T.,Co-crystals of iodopentafluorobenzene with nitrogen donors:2-D molecular assemblies through halogen bonding and aryl-perfluoroaryl interactions.CryEngComm,2007,203-206.
[9]GoroffN.S.,Curtis S.M.,Webb J.A.,Fowler F.W.,Lauher J.W.,Designed Cocrystals Based on the Pyridine-Iodoalkyne Halogen Bond.Org.Lett.,2005,7,1891-1893.
[10]Chu Q.L.,Wang Z.M.,Huang Q.C.,Yan C.H.,Zhu S.Z.,Fluorine-Containing Donor-Acceptor Complex:Infinite Chain Formed by Oxygen...Iodine Interaction.J.Am.Chem.Soc.,2001,123,11069-11070.
[11]Saha B.K.,Nangia A.,Halogen bonding and isostructurality in 2,4,6-tris-(2-halophenoxy)-1,3,5-triazines.Heteroatom Chem.,2007,18,185-194.
[12]Zordan F.,Brammer L.,Sherwood R,Supramolecular Chemistry of Halogens:Complementary Features of Inorganic(M-X) and Organic(C-X') Halogens Applied to M-X...X'-C Halogen Bond Formation.J.Am.Chem.Soc.,2005,127,5979-5989.
[13]Zordan F.,Purver S.L.,Adams H.,Brammer L.,Halometallate and halide ions:nucleophiles in competition for hydrogen bond and halogen bond formation in halopyridinium salts of mixed halide-halometallate anions.CrystEngComm,2005,350-354.
[14]LiebermaH.F.n,Davey R.J.,Newsham D.M.,Br...Br and Br."H Interactions in Action:Polymorphism,Hopping,and Twinning in 1,2,4,5-Tetrabromobenzene.Chem.Mater.,2000.12.490-494.
[15]Chowdhury M.,Kariuki B.M.,Supramolecular Assembly in Cinnamate Structures:The Influence of the Ammonium Ion and Halogen Interactions.Cryst.Growth Des.,2006,6,774-780.
[16]Metrangolo P.,Resnati G.,Halogen Bonding:A Paradigm in Supramolecular Chemistry.Chem.Eur.J.,2001,7,2511-2519.
[17]Casnati A.,Liantonio R.,Metrangolo R,Rasnati(3.,Ungaro R.,Ugozzoli F.,Molecular and Supramolecular Homochirality:Enantiopure Perfluorocarbon Rotamers and Halogen-Bonded Fluorous Double Helices.Angew.Chem.Int.Ed.,2006,45,1915-1918.
[18]Nicoson J.S.,Porrone T.F.,Hartz K.E.H.,Wang L.,Margerum D.W.,Kinetics and Mechanisms of the Reactions of Hypochlorous Acid,Chlorine,and Chlorine Monoxide with Bromite Ion.Inorg.Chem.,2003,42,5818-5824.
[19]Caronna T.,Liantonio R.,Logothetis T.A.,Metrangolo P.,Pilati T.,Resnati G.,Halogen Bonding and π...π Stacking Control Reactivity in the Solid State.J.Am.Chem.Soc.,2004,126.4500-4501.
[20]Wang F.,Ma N.,Chen Q.X.,Wang W.B.,Wang L.Y.,Halogen Bonding as a New Driving Force for Layer-by-Layer Assembly.Langmuir,2007,23,9540-9542.
[21]Bertani R.,Metrangolo R,Moiana A.,Perez E.,Pilati T.,Resnati G.,Rico-Lattes I.,Sassi A.,Supramolecular Route to Fluorinated Coatings:Self-Assembly Between Poly(4-vinylpyridines) and Haloperfluorocarbons.Adv.Mater,2002,14,1197-1201.
[22]Ngugen H.L.,Horton R N.,Hursthouse M.B.,Legon A.C.,Bruce D.W.,Halogen Bonding:ANew Interaction for Liquid Crystal Formation.J.Am.Chem.Soc.,2004,126,16-17.
[23]Xu J.W.,Liu X.M.,Lin T.T.,Huang J.C.,He C.B.,Synthesis and Self-Assembly of Difunctional Halogen-Bonding Molecules:A New Family of Supramolecular Liquid-Crystalline Polymers.Macromolecules,2005,38,3554-3557.
[24]Ferraris J.P.,Cowan D.D.,Walatka V.,Perlstein J.H.,Electron transfer in a new highly conducting donor-acceptor complex.J.Am.Chem.Soc.,1973,95,948-951.
[25]Gompper R.,Hock J.,Polbom K.,Dormann E.,Winter H.,The radical cation iodide of the new electron donor tetraiodotetrathiafulvalene:Magnetic properties and crystal structure.Adv.Mater.,1995,7,41-43.
[26] Imakubo T., Sawa H., Kato R., Synthesis and crystal structure of the molecular metal based on iodine-bonded π-donor. J. Chem. Soc. Chem. Commun. 1995, 1097-1098.
[27] Fourmigue M., Batail P., Activation of Hydrogen- and Halogen-Bonding Interactions in Tetrathiafulvalene-Based Crystalline Molecular Conductors. Chem. Rev., 2004, 104, 5379-5418.
[28] Ueda K., Sugimoto T., Faulmann C., Cassoux P., Synthesis, Crystal Structure, and Electrical Properties of Novel Radical Cation Salts of Iodine-Substituted TTF-Derived Donors with the Nitroprusside Anion Exhibiting Strong -I…NC- Interactions. Eur. J. Inorg. Chem., 2003, 12, 2333-2338.
[29] Takeuchi T., Minato Y. J., Takase M., Shinmori H., Molecularly imprinted polymers with halogen bonding-based molecular recognition sites. Tetrahedron Lett., 2005, 46, 9025-9027.
[30] Tanaka K., Fujimoto D., Oeser T., Irngartinger H., Toda F., Chiral inclusion crystallization of tetra(p-bromophenyl)ethylene by exposure to the vapor of achiral guest molecules: a novel racemic-to-chiral transformation through gas-solid reaction. Chem. Commun., 2000, 413-414.
[31] Mele A., Metrangolo P., Neukirch H., Pilati T., Resnati G., A Halogen-Bonding-Based Heteroditopic Receptor for Alkali Metal Halides. J. Am. Chem. Soc, 2005, 127, 14972-14973.
[32] Casnati A., Liantonio R., Metrangolo P., Rasnati G, Ungaro R., Ugozzoli F., Molecular and Supramolecular Homochirality: Enantiopure Perfluorocarbon Rotamers and Halogen-Bonded Fluorous Double Helices. Angew. Chem. Int. Ed, 2006,45, 1915-1918.
[33] Caronna T., Liantonio R., Logothetis T. A., Metrangolo P., Pilati T., Resnati G., Halogen Bonding and π…π Stacking Control Reactivity in the Solid State. J. Am. Chem. Soc, 2004, 126, 4500-4501.
[34] Manas G., Metrangolo P., Meyer F., Pilati T., Resnati G., Vij A., Solid state synthesis under supramolecular control of a 2D heterotetratopic self-complementary tecton tailored to halogen bonding. New J. Chem., 2006, 1397-1402.
[35] Steinrauf L. K., Hamilton J. L., Braden B. C., X-ray Crystal Structure of the Ala-109 I) Thr Variant of Human Transthyretin Which Produces Euthyroid Hyperthyroxinem. J. Biol. Chem., 1993,268,2425-2430.
[36] Shen Z., Mitra S. N., Wu W., Chen Y., Yang Y., Qin J., Hazen S. L., Eosinophil Peroxidase Catalyzes Bromination of Free Nucleosides and Double-Stranded DNA. Biochem., 2001, 40,2041-2051.
[37] Voth A. R., Hays F. A., Ho P. S., Directing macromolecular conformation through halogen bonds. PNAS, 2007, 104, 6188-6193.
[38] Jiang Y, Alcaraz A. A., Chen J. M., Kobayshi H., Lu Y. J., Snyder J. P., Diastereomers of Dibromo-7-epi-10-deacetylcephalomannine: Crowded and Cytotoxic Taxanes Exhibit Halogen Bonds. J. Med. Chem., 2006,49, 1891-1899.
[39] Bent H. A., Structural chemistry of donor-acceptor interactions. Chem. Rev., 1968, 68, 587-648.
[40] Lommerse J. P. M., Stone A. J., Taylor R., Allen F. H., The Nature and Geometry of Intermolecular Interactions between Halogens and Oxygen or Nitrogen. J. Am. Chem. Soc, 1996, 118,3108-3116.
[41] Desiraju G. R., Harlow R. L., Cyano-halogen interactions and their role in the crystal structures of the 4-halobenzonitriles. J. Am. Chem. Soc, 1989, 111, 6757-6764.
[42] Xu K., Ho D. M., Azaaromatic chlorides: a prescription for crystal structures with extensive nitrogen-chlorine donor-acceptor interactions. J. Am. Chem. Soc, 1994, 116, 105-110.
[43] Xu K., Ho D. M., Pascal R. A., Molecular Association Mediated by Nitrogen-Chlorine Donor-Acceptor Interactions. J. Org. Chem., 1995,60,7186-7191.
[44] Blackstock S. C., Lorand J. P., Kochi J.K., Charge-transfer interactions of amines with tetrahalomethanes. X-ray crystal structures of the donor-acceptor complexes of quinuclidine and diazabicyclo [2.2.2]octane with carbon tetrabromide. J. Org. Chem., 1987, 52, 1451-1460.
[45] Lindeman S. V., Hecht J., Kochi J.K., The Charge-Transfer Motif in Crystal Engineering. Self-Assembly of Acentric (Diamondoid) Networks from Halide Salts and Carbon Tetrabromide as Electron-Donor/Acceptor Synthons. J. Am. Chem. Soc, 2003, 125, 11597-11606.
[46] Rosokha S. V., Neretin I. S., Rosokha T. Y., Kochi J.K., Charge-transfer character of halogen bonding: molecular structures and electronic spectroscopy of CBr4 and CHBr3 complexes with organic σ- and π-donors. Heteroatom Chem., 2006, 17, 449-459.
[47] Benesi H. A., Hildebrand J. H., The Charge-Transfer Motif in Crystal Engineering. Self-Assembly of Acentric (Diamondoid) Networks from Halide Salts and Carbon Tetrabromide as Electron-Donor/Acceptor Synthons. J. Am. Chem. Soc, 1949, 71, 2703-2707.
[48] Mulliken R. S., Molecular Compounds and their Spectra. II. J. Am. Chem. Soc, 1952, 74, 811-824.
[1]Auffinger P.,Hays F.A.,Westhof E.,Ho R S.,Halogen bonds in biological molecules.PNAS,2004,101,16789-16794.
[2]Metrangolo P.,Neukirch H.,Pilati T.,Resnati G.,Halogen Bonding Based Recognition Processes:A World Parallel to Hydrogen Bonding.Acc.Chem.Res.,2005,38,386-395.
[3]Wang Y.H.,Zou J.W.,Lu Y.X.,Yu H.Y.,Theoretical investigation on charge-assisted halogen bonding interactions in the complexes of bromocarbons with.some anions.Int.J.Quan.Chem.2007,107,501-506.
[4] Wei H. Q., Jin W. J., Halogen bonding: a new non-covalent interaction for driving intermolecular recognition processes. Chinese J. Anal. Chem., 2007,35, 1381-1386.
[5] Benesi H. A., Hildebrand J. H., ULTRAVIOLET ABSORPTION BANDS OF IODINE IN AROMATIC HYDROCARBONS. J. Am. Chem. Soc, 1948, 70, 2832-2833.
[6] Hassel O., Structural aspects of interatomic charge-transfer bonding. Science, 1970, 170,497-502.
[7] Metrangolo P., Resnati G., Halogen Bonding: A Paradigm in Supramolecular Chemistry. Chem. Eur. J., 2001, 7, 2511-2519.
[8] Sakurai T., Sundaralinga M., Jeffrey G. A., A nuclear quadrupole resonance and X-ray study of the crystal structure of 2,5-dichloroaniline. Acta Crystallogr., 1963, 16, 354-363.
[9] Stone A. J., Lucas J., Rowland R. S., Thornley A. E., The Nature of-Cl.cntdot.. cntdot.. cntdot. Cl- Intermolecular Interactions. J. Am. Chem. Soc, 1994,116, 4910-4918.
[10] Awwadi F. F., Willett R.D., Peterson K. A., Twamley B., The Nature of Halogen… Halogen Synthons: Crystallographic and Theoretical Studies. Chem. Eur. J. 2006, 12, 8952-8956.
[11] Metrangolo P., Pilatib T., Resnati G., Halogen bonding and other noncovalent interactions involving halogens: a terminology issue. CrystEngComm, 2006, 946-947.
[12] Ramasubbu N., Parthasarathy R., Murray-Rust P., Angular preferences of intermolecular forces around halogen centers: preferred directions of approach of electrophiles and nucleophiles around carbon-halogen bond. J. Am. Chem. Soc, 1986, 108, 4308-4314.
[13] Saha B. K., Nangia A., Nicoud J. F., Using Halogen…Halogen Interactions to Direct Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules. Cryst. Growth. Des., 2006,6,1278-1281.
[14] Lucassen A. C. B., Vartanian M., Leitus G., Van der Boom M. E. 4-Bromo-2,3,5,6-tetrafluorostilbazole: Donor and Acceptor Site for Halogen Bonding and π-Stacking in One Rigid-Rod-Type Molecule. Cryst. Growth. Des., 2005, 5, 1671-1673.
[15] Lucassen A. C. B., Zubkov T., Shimon L. J. W., Van der Boom M.E. Design, synthesis and crystal structure of a multiple donor-acceptor halogen bonded stilbazole: assembly of unimolecular interconnected helices. CrystEngComm, 2007, 538-540.
[16] Cariati E., Forni A., Biella S., Metrangolo P., Meyer F.,Resnati G., Righetto S., Tordin E.,Ugo R.,Tuning second-order NLO responses through halogen bonding.Chem.Commun.,2007,2590-25920.
[17]Aakero"y C.B.,Schultheiss N.,Desper J.,Moore C.,Attempted assembly of discrete coordination complexes into 1-D chains using halogen bonding or halogen...halogen interactions.CrystEngComm,2007,421-426.
[18]Lee B.,Guillermo M.E.,Harry A.Involving metals in halogen-halogen interactions:second-sphere Lewis acid ligands for perhalometallate ions(M-X...X'-C).CrystEngComm,2003,343-345.
[19]Fiorenzo Z.,Stephen L.P.,Harry A.,Lee B.CrystEngComm,2005,350-354.
[20]Willett R.D.,Awwadi F.,Butcher R.,The Aryl Bromine-Halide Ion Synthon and Its Role in the Control of the Crystal Structures of Tetrahalocuprate(Ⅱ) Ions.Cryst.Growth.Des.,2003,3,301-311.
[21]Awwadi F.F.,Willett R.D.,Twamley B.,The Aryl Chlorine-Halide Ion Synthon and Its Role in the Control of the Crystal Structures of Tetrahalocuprate(Ⅱ) Ions.,Cryst.Growth.Des.,2007,7,624-632.
[22]Zhu S.Z.,Xing C.H.,Xu W.,Jin G.F,Li Z.T.,Halogen Bonding and Hydrogen Bonding Coexist in Driving Self-Assembly Process.Cryst.Growth.Des.,2004,4,53-56.
[23]Pigge F.C.,Vangala V.R.,Swenson D.C.,Relative importance of X...OLC vs.X...X halogen bonding as structural determinants in 4-halotriaroylbenzenes.Chem.Commun.,2006,2123-2125.
[24]Saha B.K.,Nangia A.,Halogen Bonding and Isostructurality in 2,4,6-Tris (2-halophenoxy)-1,3,5-triazines.Heteroatom Chem.,2006,18,185-194.
[25]Skabara P.J.,Kanibolotsky A.,Render S.,Berridge R.,Crouch D.J.,Bricklebank N.,Coles S.J.,Gelbrich T.,Hursthouse M.B.The Role of Functional Nitro and Cyano Groups in the Self-Assembly of 1,3-Dithiole-2-thione-Halogen Adducts.Heteroatom Chem.,2007,18,176-184.
[26]Gonnade R.G.,Bhadbhade M.M.,Shashidhar M.S.Crystal-to-crystal transformation amongst dimorphs of racemic 2,6-di-O-(p-halo benzoyl)-myo-inositol 1,3,5-orthoformates that achieves halogen bonding contacts.CrystEngComm,2008,288-296.
[27]Gonnade R.G.,Bhadbhade M.M.,Shashidhar M.S.,Sanki A.K.Concomitant dimorphs of tri-O-[p-halobenzoyl]-myo-inositol 1,3,5-orthoformates with different halogen bonding contacts:first order crystal-to-crystal thermal phase transition of kinetic form to the thermodynamic form.Chem.commun.,2005,5870-5872.
[28]Matsumoto A.,Tanaka T.,Tsubouchi T.,Tashiro K.,Saragai S.,Nakamoto S.,Crystal Engineering for Topochemical Polymerization of Muconic Esters Using Halogen-Halogen and CH/π Interactions as Weak Intermolecular Interactions.J.Am.Chem.Soc.,2002,124,8891-8902.
[29]Lieberman H.F.,Davey R.J.,Newsham D.M.T.,BraaaBr and BraaaH Interactions in Action:Polymorphism,Hopping,and Twinning in 1,2,4,5-Tetrabromobenzene.Chem.Mater.,200,12,490-494.
[30]Bosch E.,Triangular Halogen-Halogen-Halogen Interactions as a Cohesive Force in the Structures of Trihalomesitylenes.Cryst.Growth.Des.,2002,2,299-302.
[31]Reddy C.M.,Kirchner M.T.,Gundakaram R.C.,Padmanabhan K.A.,Desiraju G.R.,Isostructurality,Polymorphism and Mechanical Properties of Some Hexahalogenated Benzenes:The Nature of Halogen...Halogen Interactions.Chem.Eur.J.,2006,12.2222-2234.
[32]Zaman M.B.,Udachin K.A.,Ripmeester J.A.Supramolecular Grid and Layer Architectures.Hydrogen Bonds and Halogen-Halogen Interactions Influenced by Bromo-,Chloro-,and Cyano-Substituted Anilic Acids.Cryst.Growth.Des.,2004,4,585-589.
[33]Desiraju G.R.,Parthasarathy R.,The nature ofhalogen.cntdot..cntdot..cntdot.halogen interactions:are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms?.J.Am.Chem.Soc.,1989,111,8725-8726.
[34]Wasilewska A.,Gdaniec M.,Pol/on'ski T.,Co-crystals of iodopentafluorobenzene with nitrogen donors:2-D molecular assemblies through halogen bonding and arylperfluoroaryl interactions.CrystEngComm.,2007,203-206.
[35]Vartanian M.,Lucassen A.C.B.,Shimon L.J.W.,Van der Boom M.E.,Cocrystallization of a Tripyridyl Donor with Perfluorinated Iodobenzene Derivatives:Formation of Different N...I Halogen Bonds Determining Network vs Plain Packing Crystals.Cryst.Growth.Des.,2008,8,786-790.
[36]Corradi E.,Meille S.V.,Messina M.T.,Metrangolo P.,Resnati G.,Perfluorocarbon-hydrocarbon self-assembly.Part 6:α,ω-Diiodoperfluoroalkanes as pseudohalogens in supramolecular synthesis. Tetrahedron Lett., 1999, 40, 7519-7523.
[37] Santis A. D., Forni A., Liantonio R., Metrangolo P., Pilati T., Resnati G., N Br Halogen Bonding: One-Dimensional Infinite Chains through the Self-Assembly of Dibromotetrafluorobenzenes with Dipyridyl Derivatives. Chem. Eur. J., 2003, 9, 3974- 3983.
[38] Burton D. D., Fontana F., Metrangolo P., Pilatid T., Resnati G., Halogen bonding driven self-assembly of (E)-1,2-diiodo-1,2-difluoroethene with nitrogen substituted hydrocarbons. Tetrahedron Lett., 2003, 44, 645-648.
[39] Lucassen A. C. B., Karton A., Leitus G., Shimon L. J. W., Martin J.M. L., Van der Boom M. E., Co-Crystallization of Sym-Triiodo-Trifluorobenzene with Bipyridyl Donors: Consistent Formation of Two Instead of Anticipated Three N I Halogen Bonds. Cryst. Growth. Des., 2007, 7, 386-392.
[40] Walsh R. B., Padgett C. W., Metrangolo P., Resnati G., Hanks T. W., Pennington W. T. Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides. Cryst. Growth. Des., 2001, 1, 165-175.
[41] Guo W. Z., Galoppini E., Gilardi R., Rydja G. I., Chen Y. H., Weak Intermolecular Interactions in the Crystal Structures of Molecules with Tetrahedral Symmetry: Diamondoid Nets and Other Motifs. Cryst. Growth. Des., 2001, 1, 231-237.
[42] Amatia M., Lelja F., Liantoniob R., Metrangolo P., Luzzatic S., Pilatid T., Resnati G., J. Fluor. Chem., 2004, 125, 629-640.
[43] Adams C. J., Bowen L. E., I…π halogen-bonding in the structures of platinum- alkynyl compounds: an overlooked supramolecular interaction. J. Chem. Soc, Dalton Trans., 2005, 2239-2240.
[44] Rosokha S. V., Neretin I. S., Rosokha T. Y., Hecht J., Kochi J. K., Charge-Transfer Character of Halogen Bonding: Molecular Structures and Electronic Spectroscopy of Carbon Tetrabromide and Bromoform Complexes with Organic σ- and π-Donors. Heteroatom Chem., 2006, 17, 449-459.
[45] Meyer E. A., Castellano R. K., Diederich F., Interactions with Aromatic Rings in Chemical and Biological Recognition. Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
[46] Hunter C. A., Sanders J. K. M., The Nature of π-π Interactions. J. Am. Chem. Soc. 1990,112,5525-5534.
[1]Itokazu M.K.,Polo A.S.,Faria D.A.,Bignozzi C.A.,Syntheses and spectroscopic characterization of fac-[Re(CO)_3(phen)(L)]PF_6,L=trans- and cis-1,2-bis(4-pyridyl)ethylene.Inorg.Chim.Acta,2001,313,149-155.
[2]Li X..H.,Yang S.Z.,Xiao H.R,Synthesis and Crystal Structure of Two Interpenetrated Open Frameworks with Different Structural Motifs.Cryst.Growth Des.,2006,6,2392-2397.
[3]Lavallee D.K.,Fleischer E.B.,Charge delocalization in pentaammineruthenium(Ⅱ)complexes.Ⅱ.Dipentaammineruthenium(Ⅱ) complexes of pyrazine,4,4'-bipyridine,and 1,2-bis(4-pyridyl) ethylene.J.Am.Chem.Soc.,1972,94,2599-2601.
[4]Pizzotti M.,Ugo R.,Roberto D.,Bruni S.,Organometallic Counterparts of Push-Pull Aromatic Chromophores for Nonlinear Optics:Push-Pull Heteronuclear Bimetallic Complexes with Pyrazine and trans-l,2-Bis(4-pyridyl)ethylene as Linkers.Organometallics,2002,21,5830-5840.
[5]Sun S.S.,Auspach J.A.,Lees A.J.,Self-Assembly of Transition-Metal-Based Macrocycles Linked by Photoisomerizable Ligands:Examples of Photoinduced Conversion of Tetranuclear- Dinuclear Squares.Inorg.Chem.,2002,41,1862-1869.
[6]Argazzi R.,Bertolasi E.,Chiorboli C.,Bignozzi C.A.,Itokazu M.K.,Iha N.Y.M.,Intramolecular Energy Transfer Processes in Binuclear Re-Os Complexes.Inorg.Chem.,2001,40,6885-6891.
[7]Jude H.,Bauer J.A.K.,Connick W.B.,Luminescent Platinum(II) Dimers with a Cyclometallating Aryldiamine Ligand.Inorg.Chem.,2005,44,I211-1220.
[8]Toma H.E.,Nikolaou S.,Eberlin M.N.,Tomazela D.M.,Synthesis,properties and gas phase collision-induced dissociation of the heptanuclear doubly bridged complex [Ru(bpy)_2(BPE)_2{Ru_3O(CH_3COO)_6(py)_2}_2](PF_6)_4.Polyhedron,2005,24,731-738.
[9]Li X..J.,Cao R.,Sun D..F.,Bi W.H.,Wang Y.Q.,Li X..,Hong M.C.,Syntheses and Characterizations of Zinc(Ⅱ) Compounds Containing Three-Dimensional Interpenetrating Diamondoid Networks Constructed by Mixed Ligands.Cryst.Growth Des.,2004,4,775-780.
[10]Slone R.V.,Hupp J.T.,Stern C.L.,Alrvecht-Schmitt T.E.,Self-Assembly of Luminescent Molecular Squares Featuring Octahedral Rhenium Comers.Inorg.Chem.,1996,35,4096-4097
[11] Forni A., Metrangolo P., Pilati T., Resnati G., Halogen Bond Distance as a Function of Temperature. Cryst. Growth Des., 2004, 4, 291-295.
[12] A. D.Santis, A. Forni, R. Liantonio, P. Metrangolo, T. Pilat G. Resnati, N…Br Halogen Bonding: One-Dimensional Infinite Chains through the Self-Assembly of Dibromo-tetrafluorobenzenes with Dipyridyl Derivatives. Chem. Eur. J., 2003, 99, 3974-3983.
[13] Walsh R. B., Padgett C. D., Metrangolo P., Resnati G., Hanks T. W., Pennington W. T., Crystal Engineering through Halogen Bonding: Complexes of Nitrogen Heterocycles with Organic Iodides. Cryst. Growth Des., 2001, 1, 165-175.
[14] Guido E., Metrangolo P., Panzeri W., Pilati T., Resnati G., Ursini M., Logothetis T. A., Pentaerythritol tetrakis(4-iodo-2,3,5,6-tetrafluorophenyl) ether: a tecton for the self-assembly of double strand 1D infinite chains. J. Fluo. Chem., 2005, 126, 197-207.
[15] Lucassen A. C. B., Karton A., Leitus G., Shimon L. J. W., Martin J. M. L., Van Der Boom M. E., Co-Crystallization of Sym-Triiodo-Trifluorobenzene with Bipyridyl Donors: Consistent Formation of Two Instead of Anticipated Three N…I Halogen Bonds. Cryst. Growrh Des., 2007, 7, 386-392.
[16] Baer A. J., Macartney D. H., α-and β-Cyclodextrin Rotaxanes of μ-Bis(4-pyridyl) bis[pentacyanoferrate(II)] Complexes. Inorg. Chem., 2000, 39, 1410-1417.
[17] Wylie R. S., Macartney D. H., Effects of cyclodextrin inclusion on the kinetics of the ligand substitution reactions of aquapentacyanoferrate(II) and pentacyano (N-heterocycle) ferrate(II) complexes in aqueous media. Inorg. Chem., 1993, 32, 1830-1837.
[18] Muraka T., Kinbara K., Aida T., A Self-Locking Molecule Operative with a Photoresponsive Key. J. Am. Chem. Soc, 2006, 128, 11600-11605.
[19] Polo A. S., Itokazu M. K., Frin K. M., Patrocinio A. O. de T., Iha N. Y. M., Light driven trans-to-cis isomerization of stilbene-like ligands in fac-[Re(CO)_3(NN) (trans-L)] + and luminescence of their photoproducts. Coord. Chem. Rev., 2006,250, 1669-1680.
[20] Kanust J. M., Keller S. W., A Mixed-Ligand Coordination Polymer from the in Situ, Cu(I)-Mediated Isomerization of Bis(4-pyridyl)ethylene. Inorg. Chem., 2002, 41, 5650-5652.
[21] Alvaro M., Ferrer B., Garcia H., Rey F., Photochemical modification of the surface area and tortuosity of a trans-1,2-bis(4-pyridyl)ethylene periodic mesoporous MCM organosilica. Chem. Commun., 2002, 2012-2013.
[22]Itokazu M.K.,Polo A.S.,Iha N.Y.M.,Luminescent rigidochromism offac-[Re(CO)3(phen)(cis-bpe)]+ and its binuclear complex as photosensors.J.Photochem.photobio.A,2003,160,27-32.
[23]Qu D.H.,Ji F.Y.,Wang Q.C.,Tian H.,A Double INHIBIT Logic Gate Employing Configuration and Fluorescence Changes.Adv.Mater.,2006,18,2035-2038.
[24]Qu D.H.,Wang Q.C.,Tian H.,A Half Adder Based on a Photochemically Driven
[2]Rotaxane.Angew.Chem.Int.Ed.,2005,44,5296-5299.
[25]Grabowski Z.R.,Rotkiewicz K.,Rettig W.,Structural Changes Accompanying Intramolecular Electron Transfer:Focus on Twisted Intramolecular Charge-Transfer States and Structures.Chem.Rev.,2003,103,3899-4032.
[26]Wang Z.X.,Zheng G.R.,P.Lu,9-(Cycloheptatrienylidene)-fluorene Derivative:Remarkable Ratiometric pH Sensor and Computing Switch with NOR Logic Gate.Org.Lett.,2005,7,3669-3672.
[27]Hong S.W.,Kim K.H.,Transfer J.H.,Design and Synthesis of a New pH Sensitive Polymeric Sensor Using Fluorescence Resonance Energy Transfer.Chem.Mater.,2005,17,6213-6215.
[28]Tanaka K.,Kumagai T.,Aoki H.,Application of 2-(3,5,6-Trifluoro-2-hydroxy-4-methoxyphenyl)benzoxazole and -benzothiazole to Fluorescent Probes Sensing pH and Metal Cations.J.Org.Chem.,2001,66,7328 -7333.
[29]Cui D.W.,Qian X.H.,Liu F.Y.,Zhang R.,Novel Fluorescent pH Sensors Based on Intramolecular Hydrogen Bonding Ability of Naphthalimide.Org.Lett.,2004,6,2757-2760.
[30]Letard J.F.,Lapouyade R.,Rettig W.,Relaxation pathways in photoexcited electron-rich stilbenes(D---D stilbenes) as compared to D---A stilbenes.Chem.Phy Lett.,1994,222,209-216.
[31]Lavallee D.K.,Fleischer E.B.,Charge delocalization in pentaammineruthenium(Ⅱ)complexes.Ⅰ,spectral properties basicities and charge densities by NMR.J.Am.Chem.Soc.,1972,94,2583-2599.
[32]Beggiato G.,Favaro G.,Mazzucato U.,Acid-base equilibria of dipyridylethylene studies by absorption and fluorescence spectrometry.J.Heterocyclic Chem.,1970,7(3):583-587.