Discrete stack of an odd number of polarized aromatic compounds revealing the importance of net vs. local dipoles

Proceedings of the National Academy of Sciences of the United States of America

Volumn 106, Issue 26, 2009, Pages 10435-10437

  Yamauchi, Yoshihiro ^a   Yoshizawa, Michito ^b,c   Akita, Munetaka ^b   Fujita, Makoto ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

interactions; Aromatic molecule; Coordination cage; Dipole moment; Self assembly

Indexed keywords

AROMATIC COMPOUND; PYRENE 4,5 DIONE; UNCLASSIFIED DRUG; WATER; AROMATIC HYDROCARBON; POLYMER; PYRENE; PYRENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DIPOLE; MOLECULAR INTERACTION; POLARIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY ANALYSIS; BINDING SITE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BINDING SITES; CRYSTALLOGRAPHY, X-RAY; HYDROCARBONS, AROMATIC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYMERS; PYRENES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 67649831706     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0810319106     Document Type: Article

References (18)

1. Vollmann H, Becker H, Corell M, Streeck H, Langbein G (1937) Pyrene and its derivatives. Justus Liebigs Ann Chem 531:1-159.
2. Young ERR, Funk RL (1998) A practical synthesis of pyrene-4,5-dione. J Org Chem 63:9995-9996. (Pubitemid 29035164)
3. Hu J, Zhang D, Harris FW (2005) Ruthenium(III) chloride catalyzed oxidation of pyrene and 2,7-disubstitued pyrenes: An efficient, one-step synthesis of pyrene-4,5-diones and pyrene-4,5,9,10-tetraones. J Org Chem 70:707-708. (Pubitemid 40129441)
4. Wang Z, Enkelmann V, Negri F, Müllen K (2004) Rational design of helical columnar packing in single crystals. Angew Chem Int Ed 43:1972-1975. (Pubitemid 39257809)
5. Steed J W, Atwood J L (2000) Supramol Chem (John Wiley & Sons, Ltd, England).
6. Leininger S, Olenyuk B, Stang PJ (2000) Self-assembly of discrete cyclic nanostructures mediated by transition metals. Chem Rev 100:853-908.
7. Warmuth R, Yoon J (2001) Recent Highlights in hemicarcerand chemistry. Acc Chem Res 34:95-105. (Pubitemid 32167860)
8. Hof F, Craig SL, Nuckolls C, Rebek J, Jr (2002) Molecular encapsulation. Angew Chem Int Ed 41:1488-1508.
9. Fiedler D, Leung DH, Bergman RG, Raymond KN (2005) Selective molecular recognition, C-H bond activation, and catalysis in nanoscale reaction vessels. Acc Chem Res 38:349-358. (Pubitemid 40792597)
10. Fujita M, Tominaga M, Hori A, Therrien B (2005) Coordination assemblies from a Pd(II)-cornered square complex. Acc Chem Res 38:371-380. (Pubitemid 40792598)
11. Vriezema DM, et al. (2005) Self-Assembled Nanoreactors. Chem Rev 105:1445-1490. (Pubitemid 40596870)
12. Amijs CHM, van Klink GPM, van Koten G (2006) Metallasupramolecular architectures, an overview of functional properties and applications. Dalton Trans 308-327.
13. Yoshizawa M, et al. (2005) Related organic pillared cages: Discrete stacking of large aromatic molecules within organic-pillared coordination cages. Angew Chem Int Ed 44:1810-1813.
14. Kumazawa K, Biradha K, Kusukawa T, Okano T, Fujita M (2003) Multicomponent assembly of a pyrazine-pillared coordination cage that selectively binds planar guests by intercalation. Angew Chem Int Ed 42:3909-3913. (Pubitemid 37064198)
15. +., within a self-assembled cage. J Am Chem Soc 127:13456-13457.
16. Ono K, Yoshizawa M, Kato T, Fujita M (2008) Three-metal-center spin interactions through the intercalation of metal azaporphines and porphines into an organic pillared coordination box. Chem Commun 2328-2330. (Pubitemid 351691990)
17. Yamauchi Y, Yoshizawa M, Fujita M (2008) Engineering stacks of aromatic rings by the interpenetration of self-assembled coordination cages. J Am Chem Soc 130:5832-5833. (Pubitemid 351620810)
18. Hunter CA, Lawson KR, Perkins J, Urch CJ (2001) Aromatic interactions. J Chem Soc Perkin Trans 2:651-669. (Pubitemid 33270787)