Discrete stacking of large aromatic molecules within organic-pillared coordination cages.

Introduction Aromatic stacking of π-conjugated planar molecules leads to the exhibition of unique chemical and physical properties. Discotic liquid crystals are, for example, columnar assembly of aromatic compounds with long alkyl chains. Organic electroconductive materials involve alternative charge-transfer stacking of electron-donating and -accepting π-conjugated compounds. Whereas such infinite assemblies have been thoroughly studied, precisely controlled discrete assemblies composed of more than two π-conjugated molecules are much less explored. Here we report the self-assembly of a metalhinged organic-pillared cage 1 with a large cavity which can accommodate two large π-conjugated molecules. The cage consists of two large organic panels 2, three rod-like pillars 3, and six metal-hinges 4 (Figure1a). The large box-shaped cavity accommodates π-conjugated molecules in limited numbers.

[1]  K. Nakabayashi,et al.  Cavity-induced spin-spin interaction between organic radicals within a self-assembled coordination cage. , 2004, Journal of the American Chemical Society.

[2]  M. Fujita,et al.  A palladium(II)-clipped aromatic sandwich. , 2004, Angewandte Chemie.

[3]  M. Fujita,et al.  Alkane oxidation via photochemical excitation of a self-assembled molecular cage. , 2004, Journal of the American Chemical Society.

[4]  M. Tamura,et al.  AND/OR bimolecular recognition. , 2004, Journal of the American Chemical Society.

[5]  Michael B Hursthouse,et al.  Halogen bonding: a new interaction for liquid crystal formation. , 2004, Journal of the American Chemical Society.

[6]  A. Spek,et al.  Regulatory strategies in the complexation and release of a noncovalent guest trimer by a self-assembled molecular cage. , 2003, Angewandte Chemie.

[7]  A. J. Goshe,et al.  Molecular recognition. Self-assembly of molecular trigonal prisms and their host-guest adducts. , 2003, Chemical communications.

[8]  K. Biradha,et al.  Multicomponent assembly of a pyrazine-pillared coordination cage that selectively binds planar guests by intercalation. , 2003, Angewandte Chemie.

[9]  K. Biradha,et al.  Side chain-directed assembly of triangular molecular panels into a tetrahedron vs. open cone. , 2003, Chemical communications.

[10]  K. Yamaguchi Cold-spray ionization mass spectrometry: principle and applications. , 2003, Journal of mass spectrometry : JMS.

[11]  R. Purrello,et al.  Non-covalent synthesis in aqueous solution of discrete multi-porphyrin aggregates with programmable stoichiometry and sequence. , 2002, Journal of the American Chemical Society.

[12]  Owen R. Lozman,et al.  Discotic liquid crystals 25 years on , 2002 .

[13]  U. Wille Self-terminating, oxidative radical cyclizations: a novel reaction of acyloxyl radicals. , 2002, Journal of the American Chemical Society.

[14]  R. Purrello,et al.  Calixarene-Porphyrin Supramolecular Complexes: pH-Tuning of the Complex Stoichiometry. , 2001, Angewandte Chemie.

[15]  A. Lees,et al.  One-step self-assembly organometallic molecular cages from 11 components , 2001 .

[16]  M. Fujita,et al.  Spontaneous assembly of ten components into two interlocked, identical coordination cages , 1999, Nature.

[17]  M. Fujita,et al.  Self-assembly of ten molecules into nanometre-sized organic host frameworks , 1995, Nature.

[18]  Alan J. Heeger,et al.  Superconducting fluctuations and the Peierls instability in an organic solid , 1993 .

[19]  John P. Ferraris,et al.  Electron transfer in a new highly conducting donor-acceptor complex , 1973 .