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Volumn 72, Issue 3, 2007, Pages 938-944

Intramolecular π-stacking interaction in a rigid molecular hinge substituted with 1-(pyrenylethynyl) units

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; FLUORESCENCE; GROUND STATE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONS; SYNTHESIS (CHEMICAL);

EID: 33846904541     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062173y     Document Type: Article
Times cited : (95)

References (60)
  • 28
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    • For anion-mediated π stacking, see
    • (c) For anion-mediated π stacking, see: Suzuki, I.; Ui, M.; Yamauchi, A. J. Am. Chem. Soc. 2006, 128, 4498-4499.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 4498-4499
    • Suzuki, I.1    Ui, M.2    Yamauchi, A.3
  • 37
    • 33846903476 scopus 로고    scopus 로고
    • Ref 6b
    • (a) Ref 6b.
  • 40
    • 0027788075 scopus 로고
    • For an NMR study of π-π stacking of pheophytin, see
    • (d) For an NMR study of π-π stacking of pheophytin, see: Hynninen, P. H.; Lötjönen, S. Biochem. Biophys. Acta 1993, 1083, 374-380.
    • (1993) Biochem. Biophys. Acta , vol.1083 , pp. 374-380
    • Hynninen, P.H.1    Lötjönen, S.2
  • 41
    • 0002828104 scopus 로고    scopus 로고
    • For the spectral data of [2,2]-2,7-pyrenophane, see: Umemoto, T.; Satani, S.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1975, 3159-3162.
    • For the spectral data of [2,2]-2,7-pyrenophane, see: Umemoto, T.; Satani, S.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1975, 3159-3162.
  • 42
    • 33846915605 scopus 로고    scopus 로고
    • Intermolecular π-π interactions in benzene and naphthalene can occur through a T-shaped geometry. Calculations show that the minimum energy configuration is a T-shape. However, in polycyclic aromatic hydrocarbons such as pyrene and coronene and porphyrins, it is the displaced parallel stacking that is observed in the solid state. In such systems, the T-shaped geometry does not contribute to the π-stacking interactions. See refs 3a and 9c. See also: Desiraju, G. R. Crystal Engineering. The Design of Organic Solids; Elsevier: Amsterdam, 1989; pp 92-96.
    • Intermolecular π-π interactions in benzene and naphthalene can occur through a T-shaped geometry. Calculations show that the minimum energy configuration is a T-shape. However, in polycyclic aromatic hydrocarbons such as pyrene and coronene and porphyrins, it is the displaced parallel stacking that is observed in the solid state. In such systems, the T-shaped geometry does not contribute to the π-stacking interactions. See refs 3a and 9c. See also: Desiraju, G. R. Crystal Engineering. The Design of Organic Solids; Elsevier: Amsterdam, 1989; pp 92-96.
  • 43
  • 46
    • 25144457993 scopus 로고    scopus 로고
    • The binding energy of the homo π dimers for benzene and naphthalene is calculated to be 3-10 kcal/mol depending upon the geometry of the dimers; see: Sato, T.; Tsuneda, T.; Hirao, K. J. Chem. Phys. 2005, 123, 104307-1-104307-10.
    • The binding energy of the homo π dimers for benzene and naphthalene is calculated to be 3-10 kcal/mol depending upon the geometry of the dimers; see: Sato, T.; Tsuneda, T.; Hirao, K. J. Chem. Phys. 2005, 123, 104307-1-104307-10.
  • 47
    • 0035938286 scopus 로고    scopus 로고
    • For hindered rotation of a triple bond, see: a
    • For hindered rotation of a triple bond, see: (a) Toyota, S.; Yamamori, T.; Makino, T. Tetrahedron 2001, 57, 3521-3528.
    • (2001) Tetrahedron , vol.57 , pp. 3521-3528
    • Toyota, S.1    Yamamori, T.2    Makino, T.3
  • 53
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    • See also ref 10b
    • (b) See also ref 10b.
  • 56
    • 0001579122 scopus 로고    scopus 로고
    • A similar blue shift of the pyrene excimer emission with increasing temperature has been reported earlier; see: (a) Lou, J, Hatton, T. A, Laibinis, P. E. Anal. Chem. 1997, 69, 1262-1264
    • A similar blue shift of the pyrene excimer emission with increasing temperature has been reported earlier; see: (a) Lou, J.; Hatton, T. A.; Laibinis, P. E. Anal. Chem. 1997, 69, 1262-1264.
  • 57
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    • See also ref 8b
    • (b) See also ref 8b.
  • 60
    • 33846925796 scopus 로고    scopus 로고
    • In spite of repeated purification by recrystallization, elemental analysis of compounds 6 and 1 always gave lower values for the carbon content, presumably due to incomplete combustion of these carbon-rich molecules. Formation of black soot during the violent decomposition of 6 was evident during its melting point determination.
    • In spite of repeated purification by recrystallization, elemental analysis of compounds 6 and 1 always gave lower values for the carbon content, presumably due to incomplete combustion of these carbon-rich molecules. Formation of black soot during the violent decomposition of 6 was evident during its melting point determination.


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