Topochemical limits for solid-state photoreactivity by fine tuning of the pi-pi interactions.

The limiting topochemical criteria for photodimerization were studied by modulation of the pi-pi stacking interactions between self-templating planar molecules with hydrogen bonding. The product yield and composition can be controlled predominantly by the distance between the reactive bonds.

[1]  H. Uekusa,et al.  Elongated Lifetime of Unstable Colored Species by Intermolecular Hydrogen Bond Formation in Photochromic Crystals , 2009 .

[2]  Giannis S. Papaefstathiou,et al.  Supramolecular control of reactivity in the solid state: from templates to ladderanes to metal-organic frameworks. , 2008, Accounts of chemical research.

[3]  Paul W Ayers,et al.  Understanding the Woodward-Hoffmann rules by using changes in electron density. , 2007, Chemistry.

[4]  P. Naumov,et al.  Direct observation of aminyl radical intermediate during single-crystal to single-crystal photoinduced Orton rearrangement. , 2007, The journal of physical chemistry. B.

[5]  M. Messerschmidt,et al.  Single-crystal-to-single-crystal E --> Z isomerization of tiglic acid in a supramolecular framework. , 2007, Acta crystallographica. Section B, Structural science.

[6]  K. Houk,et al.  The photoarrangement of alpha-santonin is a single-crystal-to-single-crystal reaction: a long kept secret in solid-state organic chemistry revealed. , 2007, Journal of the American Chemical Society.

[7]  L. MacGillivray,et al.  Metal-mediated reactivity in the organic solid state: from self-assembled complexes to metal-organic frameworks. , 2007, Chemical Society reviews.

[8]  K. Ariga,et al.  Structural study of the thermally induced and photoinduced phase transitions of the 1,3,5-trithia-2,4,6-triazapentalenyl (TTTA) radical. , 2007, The journal of physical chemistry. A.

[9]  P. Ayers,et al.  Woodward-Hoffmann rules in density functional theory: initial hardness response. , 2006, The Journal of chemical physics.

[10]  J. Mague,et al.  Volume-demanding cis-trans isomerization of 1,2-diaryl olefins in the solid state. , 2006, The Journal of organic chemistry.

[11]  Peddy Vishweshwar,et al.  The predictably elusive form II of aspirin. , 2005, Journal of the American Chemical Society.

[12]  P. Cozzi.  Metal-Salen Schiff base complexes in catalysis: practical aspects. , 2004, Chemical Society reviews.

[13]  J. L. Gleason,et al.  Two birds with one metallic stone: single-pot catalysis of fundamentally different transformations. , 2004, Angewandte Chemie.

[14]  E. Nesterov,et al.  Development of experimental and theoretical crystal lattice organic photochemistry: the quantitative cavity. Mechanistic and exploratory organic photochemistry. , 2002, Accounts of chemical research.

[15]  M. Zaworotko,et al.  From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. , 2001, Chemical reviews.

[16]  A. Gavezzotti,et al.  Attractions and Repulsions in Molecular Crystals: What Can Be Learned from the Crystal Structures of Condensed Ring Aromatic Hydrocarbons? , 1999 .

[17]  G. Montandon,et al.  Synthesis and luminescence spectroscopy of YNbO4 doped with Eu(III) , 1998 .

[18]  W. Jones.  Organic Molecular Solids: Properties and Applications , 1997 .

[19]  H. L. Carrell,et al.  3-(3',5'-Dinitrophenyl)-4-(2',5'-dimethoxyphenyl)cyclobutane-1,2-dicarboxylic Acid: Engineered Topochemical Synthesis and Molecular and Supramolecular Properties , 1994 .

[20]  T. Mallouk,et al.  Topochemical diacetylene polymerization in layered metal phosphate salts , 1991 .

[21]  G. Desiraju,et al.  Unusual [2 + 2] topochemical cycloadditions of 3-cyano- and 4-cyano-cinnamic acids: temperature dependent solid state photochemical reactions , 1991 .

[22]  Y. Ohashi.  Dynamical structure analysis of crystalline-state racemization , 1988 .

[23]  Vaidhyanathan Ramamurthy,et al.  Photochemical reactions of organic crystals , 1987 .

[24]  V. Ramamurthy,et al.  Topochemical solid state photodimerization of non-ideally oriented monomers: 7-chlorocoumarin and 7-methoxycoumarin , 1984 .

[25]  H. Meier,et al.  A Simple Route to a New Type of Cyclophane , 1981 .

[26]  A. W. Hanson.  Methyl 4-hydroxy-3-nitro-trans-cinnamate , 1975 .

[27]  Roald Hoffmann,et al.  Conservation of orbital symmetry , 1968 .

[28]  Roald Hoffmann,et al.  Stereochemistry of Electrocyclic Reactions (福井謙一とフロンティア軌導理論) -- (参考論文) , 1965 .

[29]  M. D. Cohen,et al.  383. Topochemistry. Part I. A survey , 1964 .