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Volumn 5, Issue 2, 1999, Pages 546-556

Self-assembly of Janus cyclodextrins at the air-water interface and in organic solvents

Author keywords

Cyclodextrins; Hydrogen bonds; Monolayers; Self assembly; Structural elucidation

Indexed keywords

CYCLODEXTRIN DERIVATIVE; ORGANIC SOLVENT;

EID: 0033046267     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990201)5:2<546::AID-CHEM546>3.0.CO;2-I     Document Type: Article
Times cited : (24)

References (56)
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    • Electrospray experiments suggest that 1β remains monomeric in a mixture of water and acetonitrile, see: M. Eddaoudi, A. W. Coleman, P. Prognon, P. Lopez-Mahia, J. Chem. Soc. Perkin Trans. 2 1996, 955-959. Nevertheless, the latter result is difficult to analyze for extracting the extrapolated associative behavior in pure water, since specific solvation of 1β by acetonitrile is expected to occur in water-acetonitrile mixtures, even at low acetonitrile molar fractions.
    • (1996) J. Chem. Soc. Perkin Trans. 2 , pp. 955-959
    • Eddaoudi, M.1    Coleman, A.W.2    Prognon, P.3    Lopez-Mahia, P.4
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    • For side-on arrangement see: A. Laschewsky, Adv. Mater. 1989, 1, 392-395.
    • (1989) Adv. Mater. , vol.1 , pp. 392-395
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    • note
    • No splitting of signals that could appear under the assumption of a slow exchange regime has been observed in the course of the present study.
  • 15
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    • note
    • 2 ≈ 6.5 ppm that is in satisfactory agreement in sign and order of magnitude with the expected shielding effect from the benzene ring current.
  • 18
    • 85033965851 scopus 로고    scopus 로고
    • note
    • The corresponding VPO experiments are not reliable at low concentration due to impurities in the solvents. Pure chloroform is unstable and known to contain hydrogen chloride, whereas THF contains water; this would affect the measurements in these solvents.
  • 20
    • 85033959871 scopus 로고    scopus 로고
    • note
    • Slowly is taken here as the timescale of elution: 1-10 min.
  • 21
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    • The group of A. Coleman has already extensively investigated the complexing properties of 1β at the air-water interface. For an example of ion complexation, see: M. Eddaoudi, A. Baszkin, H. Parrot-Lopez, M. M. Boissonade, A. W. Coleman, Langmuir 1995, 11, 13-15; for an example of complexation of neutral organic molecules, see: M. Eddaoudi, A. W. Coleman, A. Baszkin, Supramol. Chem. 1997, 8, 177-180.
    • (1995) Langmuir , vol.11 , pp. 13-15
    • Eddaoudi, M.1    Baszkin, A.2    Parrot-Lopez, H.3    Boissonade, M.M.4    Coleman, A.W.5
  • 22
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    • The group of A. Coleman has already extensively investigated the complexing properties of 1β at the air-water interface. For an example of ion complexation, see: M. Eddaoudi, A. Baszkin, H. Parrot-Lopez, M. M. Boissonade, A. W. Coleman, Langmuir 1995, 11, 13-15; for an example of complexation of neutral organic molecules, see: M. Eddaoudi, A. W. Coleman, A. Baszkin, Supramol. Chem. 1997, 8, 177-180.
    • (1997) Supramol. Chem. , vol.8 , pp. 177-180
    • Eddaoudi, M.1    Coleman, A.W.2    Baszkin, A.3
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    • b) J. Majewski, R. Edgar, R. Popovitz-Biro, K. Kjaer, W. Bouwman, J. Als-Nielsen, M. Lahav, L. Leiserowitz, Angew. Chem. 1995, 107, 707-711; Angew. Chem. Int. Ed. Engl. 1995, 34, 649-652.
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  • 37
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    • note
    • In particular, the agreement suggests that the lifetime of the solvent molecules on cyclodextrin surfaces exceeds several nanoseconds. Otherwise, slip boundary conditions would apply and the friction coefficient for rotation would be zero. See for instance the ref. [4].
  • 38
    • 85033966943 scopus 로고    scopus 로고
    • note
    • If one takes a larger diameter D as a mean to increase the friction at the ends of the cylinder, the equilibrium distance d between 1β interacting units is strongly reduced. For instance with D = 2.2 nm, one obtains a minimum of F at L = 3.3 nm that gives d = 0.7 nm.
  • 39
    • 0026694737 scopus 로고
    • The different behaviour of 3β can be explained by the absence of hydroxyl groups on the secondary face of the cyclodextrin. When they exist, the latter hydroxyl groups form an intramolecular network of hydrogen bonds that gives its rigidity to the cyclodextrin skeleton, see for instance: K. B. Lipkowitz, K. Green, J. Yang, Chirality 1992, 4, 205-215; K. B. Lipkowitz, J. Org. Chem. 1991, 56, 6357-6367. Consequently, 1β and 2β should exhibit similar cyclodextrin backbones and thus close arrangement of 6-glucose substituents whereas the primary face of 3β could be arranged in a different way.
    • (1992) Chirality , vol.4 , pp. 205-215
    • Lipkowitz, K.B.1    Green, K.2    Yang, J.3
  • 40
    • 0026318346 scopus 로고
    • The different behaviour of 3β can be explained by the absence of hydroxyl groups on the secondary face of the cyclodextrin. When they exist, the latter hydroxyl groups form an intramolecular network of hydrogen bonds that gives its rigidity to the cyclodextrin skeleton, see for instance: K. B. Lipkowitz, K. Green, J. Yang, Chirality 1992, 4, 205-215; K. B. Lipkowitz, J. Org. Chem. 1991, 56, 6357-6367. Consequently, 1β and 2β should exhibit similar cyclodextrin backbones and thus close arrangement of 6-glucose substituents whereas the primary face of 3β could be arranged in a different way.
    • (1991) J. Org. Chem. , vol.56 , pp. 6357-6367
    • Lipkowitz, K.B.1
  • 41
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    • note
    • As already underlined, we suppose that the hydroxyl group at the C3 glucose position is engaged in an intramolecular hydrogen bond with the oxygen at the C′2 position of the neighbouring glucose unit. Consequently, we do not take into account the corresponding hydroxyl groups for discussing the dimerization process.
  • 42
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    • This value compares well with other systems with hydrogen bond interactions. See for instance: H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engt. 1991, 30, 1417-1436.
    • (1991) Angew. Chem. , vol.103 , pp. 1419-1439
    • Schneider, H.-J.1
  • 43
    • 0026054712 scopus 로고
    • This value compares well with other systems with hydrogen bond interactions. See for instance: H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439; Angew. Chem. Int. Ed. Engt. 1991, 30, 1417-1436.
    • (1991) Angew. Chem. Int. Ed. Engt. , vol.30 , pp. 1417-1436
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  • 51
    • 85033973580 scopus 로고    scopus 로고
    • note
    • To calculate the simulated NOEF, the average over the seven glucose residues present in the β-cyclodextrin backbone can be performed either by averaging the θ angles, the respective spectral density functions, or the NOEF. Whichever the way which is chosen, the averaging yields essentially the same results at the precision of the present experimental determination.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.