Molecular Recognition at Crystal Interfaces

Nucleation, growth, and dissolution of crystals have been studied by stereochemical approach involving molecular recognition at interfaces. A methodology is described for using ``tailor-made'' additives designed to interact stereospecifically with crystal surfaces during growth and dissolution. This procedure was instrumental in controlling crystal morphology and in revising the concept of the structure and symmetry of solid solutions. Consequently, it was applied to the transformation of centrosymmetric single crystals into solid solutions with polar arrangement displaying second-harmonic generation and to the performance of asymmetric synthesis of guest molecules inside centrosymmetric host crystals. The method has led to a discovery of a new ``relay'' mechanism explaining the effect of solvent on crystal growth. Finally, it allowed for the design of auxiliary molecules that act as promoters or inhibitors of crystal nucleation that can be used to resolve enantiomers and crystallize desired polymorphs.

[1]  J. Mayer,et al.  An electron microscopy study of defect structures in recrystallized amorphous layers of self-ion-irradiated 〈111〉 silicon , 1978 .

[2]  G. Meredith,et al.  Centrosymmetric crystals as host matrices for second-order optical nonlinear effects , 1989 .

[3]  T. Koetzle,et al.  Precision neutron diffraction structure determination of protein and nucleic acid components. VI. The crystal and molecular structure of the amino acid l‐asparagine monohydrate , 1972 .

[4]  E. Landau,et al.  Stereochemical studies in crystal nucleation. Oriented crystal growth of glycine at interfaces covered with Langmuir and Langmuir-Blodgett films of resolved .alpha.-amino acids , 1989 .

[5]  L. Addadi,et al.  Absolute asymmetric photochemistry using centrosymmetric single crystals: the host/guest system (E)-cinnamamide/(E)-cinnamic acid , 1989 .

[6]  A. Kvick,et al.  Deformation electron density of α-glycine at 120 K , 1980 .

[7]  K. Kjaer,et al.  Elucidation of the two-dimensional structure of an α-amino acid surfactant monolayer on water using synchrotron X-ray diffraction , 1987, Nature.

[8]  E. Landau,et al.  Langmuir Monolayers Designed for the Oriented Growth of Glycine and Sodium Chloride Crystals at Air/Water Interfaces , 1986 .

[9]  L. Addadi,et al.  Assignment of Absolute Structure of Polar Crystals Using Tailor-Made Additives. Solvent Surface Interactions on the Polar Crystals of α-Resorcinol, (R, S) Alanine and Y-Glycine , 1986 .

[10]  E. Landau,et al.  A Synchrotron X-ray Study of a Solid-Solid Phase Transition in a Two-Dimensional Crystal , 1988, Science.

[11]  Bm Smythe Sucrose crystal growth. III. The relative growth rates of faces and their effect on sucrose crystal shape , 1967 .

[12]  L. Addadi,et al.  Oriented crystallization as a tool for detecting ordered aggregates of water-soluble hydrophobic .alpha.-amino acids at the air-solution interface , 1990 .

[13]  J. McBride,et al.  Using Crystal Birefringence to Study Molecular Recognition , 1989 .

[14]  C. Borrmann Neuere Arbeitsmethoden zum Waschen und Destillieren von Flüssigkeiten , 1915 .

[15]  L. Addadi,et al.  Resolution of conglomerates with the assistance of tailor-made impurities. Generality and mechanistic aspects of the "rule of reversal". A new method for assignment of absolute configuration , 1982 .

[16]  E. Landau,et al.  Synchrotron X-ray study of the structure of a Langmuir monolayer and the attached solute molecular layer , 1988 .

[17]  L. Addadi,et al.  Centrosymmetric crystals for the direct assignment of the absolute configuration of chiral molecules. Application to the .alpha.-amino acids by their effect on glycine crystals , 1983 .

[18]  S. Weiner,et al.  Intercalation of sea urchin proteins in calcite: study of a crystalline composite material. , 1990, Science.

[19]  J. Bourne,et al.  The role of solvent-solute interactions in determining crystal growth mechanisms from solution: I. The surface entropy factor , 1976 .

[20]  S. Mann,et al.  Interfacial control of nucleation of calcium carbonate under organized stearic acid monolayers , 1989, Proceedings of the Royal Society of London. A. Mathematical and Physical Sciences.

[21]  L. Addadi,et al.  Molecular recognition at the solid-solution interface: a relay mechanism for the effect of solvent on crystal growth and dissolution , 1990 .

[22]  P. Hartman,et al.  Crystal growth : an introduction , 1973 .

[23]  Stephen Mann,et al.  Controlled crystallization of CaCO3 under stearic acid monolayers , 1988, Nature.

[24]  T. Koetzle,et al.  Reduction in crystal symmetry of a solid solution: a neutron diffraction study at 15 K of the host/guest system asparagine/aspartic acid , 1989 .

[25]  L. Addadi,et al.  Design of polymeric inhibitors for the control of crystal polymorphism. Induced enantiomeric resolution at racemic histidine by crystallization at 25.degree.C , 1987 .

[26]  R. Popovitz‐Biro,et al.  Ice Nucleation by Alcohols Arranged in Monolayers at the Surface of Water Drops , 1990, Science.

[27]  L. Addadi,et al.  Growth and Dissolution of Organic Crystals with “Tailor‐Made” Inhibitors—Implications in Stereochemistry and Materials Science , 1985 .

[28]  M. Idelson,et al.  Crystal morphology engineering by "tailor-made" inhibitors; a new probe to fine intermolecular interactions , 1985 .

[29]  P. Bennema,et al.  Orientational order in naphthalene crystal-solution interfaces , 1987 .

[30]  L. Addadi,et al.  Total asymmetric transformations at interfaces with centrosymmetric crystals: role of hydrophobic and kinetic effects in the crystallization of the system glycine/.alpha.-amino acids , 1988 .

[31]  R. Davey,et al.  Experimental and Theoretical Morphology of p-Nitro p'-Methyl Benzilidine Aniline, A Non-Linear Optic Material , 1988 .

[32]  K. Kjaer,et al.  Dynamics of two-dimensional self-aggregation: pressure and pH-induced structural changes in a fluorocarbon amphiphile at liquid-air interfaces. An x-ray synchrotron study , 1990 .

[33]  L. Addadi,et al.  Resolution of conglomerates by stereoselective habit modifications , 1982, Nature.

[34]  L. Shimon,et al.  The Structure and Symmetry of Crystalline Solid Solutions: A General Revision , 1988, Science.

[35]  E. Landau,et al.  Design and surface synchrotron X-ray structure analysis of Langmuir films for crystal nucleation , 1989 .