Hydrogen bond-induced rigid oligoanthranilamide ribbons that are planar and straight.

[structure: see text] A new series of oligoanthranilamides has been synthesized starting from suitably modified p-phenylenediamine and p-phthalic acid derivatives. Due to strong intramolecular three-center hydrogen bonds, the new oligomers self-assemble into highly stable straight and planar molecular ribbons, which have been characterized by X-ray crystallography and 1H NMR, IR, and UV-vis spectroscopy.

[1]  B. Gong,et al.  Evolution of Helical Foldamers , 2003 .

[2]  Jeffrey S. Moore,et al.  Shape-persistent arylene ethynylene macrocycles: syntheses and supramolecular chemistry. , 2003, Chemical communications.

[3]  Jeffrey S. Moore,et al.  Hydrogen bond-stabilized helix formation of a m-phenylene ethynylene oligomer. , 2002, Organic letters.

[4]  Keiji Hirose,et al.  m-Diethynylbenzene macrocycles: syntheses and self-association behavior in solution. , 2002, Journal of the American Chemical Society.

[5]  Matthew J. Mio,et al.  A field guide to foldamers. , 2001, Chemical reviews.

[6]  B. Iverson,et al.  Models of higher-order structure: foldamers and beyond. , 2001, Current opinion in chemical biology.

[7]  W. DeGrado,et al.  beta-Peptides: from structure to function. , 2001, Chemical reviews.

[8]  Joseph T. Hupp,et al.  Supramolecular Coordination Chemistry and Functional Microporous Molecular Materials , 2001 .

[9]  P. Stang,et al.  Self-assembly of discrete cyclic nanostructures mediated by transition metals. , 2000, Chemical reviews.

[10]  Rainer E. Martin,et al.  Linear Monodisperse π-Conjugated Oligomers: Model Compounds for Polymers and More. , 1999, Angewandte Chemie.

[11]  James S. Nowick,et al.  Chemical Models of Protein β-Sheets , 1999 .

[12]  J. Bäckvall,et al.  CHIRAL BENZOQUINONES AS A NEW CLASS OF LIGANDS FOR ASYMMETRIC CATALYSIS : SYNTHESIS AND APPLICATION TO THE PALLADIUM(II)-CATALYZED 1,4-DIALKOXYLATION OF 1,3-DIENES , 1998 .

[13]  Samuel H. Gellman,et al.  Foldamers: A Manifesto , 1998 .

[14]  M. Fujita,et al.  Metal-directed self-assembly of two- and three-dimensional synthetic receptors , 1998 .

[15]  J. Fraser Stoddart,et al.  SYNTHETIC SUPRAMOLECULAR CHEMISTRY , 1997 .

[16]  Dario M. Bassani,et al.  Designed Self‐Generation of an Extended Helical Structure From an Achiral Polyheterocylic Strand , 1997 .

[17]  D. Seebach,et al.  β-Peptides: a surprise at every turn , 1997 .

[18]  E. W. Meijer,et al.  pi-Conjugated oligomers and polymers with a self-assembled ladder-like structure , 1996 .

[19]  Y. Hamuro,et al.  Oligoanthranilamides. Non-Peptide Subunits That Show Formation of Specific Secondary Structure , 1996 .

[20]  Ashok S. Shetty,et al.  Aromatic π-Stacking in Solution as Revealed through the Aggregation of Phenylacetylene Macrocycles , 1996 .

[21]  S. Gellman,et al.  Intramolecular Hydrogen Bonding in Derivatives of .beta.-Alanine and .gamma.-Amino Butyric Acid; Model Studies for the Folding of Unnatural Polypeptide Backbones , 1994 .

[22]  J. Nowick,et al.  Molecular scaffolds. I. Intramolecular hydrogen bonding in a family of di- and triureas , 1992 .

[23]  M. C. Etter.  Encoding and decoding hydrogen-bond patterns of organic compounds , 1990 .

[24]  A. Legon.  Tilden Lecture. The properties of hydrogen-bonded dimers from rotational spectroscopy , 1990 .

[25]  J. Stoddart,et al.  The evolution of molecular belts and collars , 1989 .

[26]  N. Mikami,et al.  Electronic spectra of tolane in a supersonic free jet: Large-amplitude torsional motion , 1984 .

[27]  Horst Kessler,et al.  Conformation and Biological Activity of Cyclic Peptides , 1982 .

[28]  C. Marvel,et al.  POLYTHIOLESTERS. II. PREPARATION IN EMULSIONS , 1953 .