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Volumn 127, Issue 23, 2005, Pages 8517-8525

Polarizing a hydrophobic cavity for the efficient binding of organic guests: The case of calix[6]tren, a highly efficient and versatile receptor for neutral or cationic species

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; POSITIVE IONS; SUPRAMOLECULAR CHEMISTRY;

EID: 20444491521     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051299u     Document Type: Article
Times cited : (99)

References (67)
  • 3
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    • (c) Reviews on molecular recognition: Chem. Rev. 1997, 97, 1231-1734.
    • (1997) Chem. Rev. , vol.97 , pp. 1231-1734
  • 18
    • 33746312419 scopus 로고
    • (a) Collet, A. Tetrahedron 1987, 43, 5725-5759.
    • (1987) Tetrahedron , vol.43 , pp. 5725-5759
    • Collet, A.1
  • 45
    • 85083152766 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 47
    • 85083140252 scopus 로고    scopus 로고
    • note
    • In this system, the exchange process must be dissociative (see ref 14e). Hence, the stronger bound, the slower the guest exchange.
  • 48
    • 85083139542 scopus 로고    scopus 로고
    • note
    • a, i.e., picric acid, similar endo-complexation results were obtained.
  • 49
    • 85083128135 scopus 로고    scopus 로고
    • note
    • + due to the impossibility to determine with precision the water concentration.
  • 53
    • 85083148536 scopus 로고    scopus 로고
    • note
    • 3).
  • 54
    • 85083124164 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum due to the fast pyramidal inversion of the coordinated nitrogen atoms, see ref 26.
  • 55
    • 85083143525 scopus 로고    scopus 로고
    • note
    • CH2 = -1.45, -1.38, -1.25, -0.82, -0.38, +0.46; +0.86 ppm.
  • 56
    • 85083119380 scopus 로고    scopus 로고
    • note
    • CH2 = -1.48, -1.04, -0.58, +1.77 ppm.
  • 57
    • 85083128290 scopus 로고    scopus 로고
    • note
    • 4OH (0.1 M solution in toluene/methanol), up to 125 and 5 equiv. respectively.
  • 58
    • 85083131998 scopus 로고    scopus 로고
    • note
    • The broadness of the NMR signature of the calixarene host is due to the coalescence phenomena described above. When recorded either at lower or at higher T, it was superimposable to those shown in Figure 3, thereby demonstrating unambiguously that the species depicted by spectrum c in Figure 5 indeed corresponds to the per-protonated receptor.
  • 59
    • 85083128062 scopus 로고    scopus 로고
    • note
    • The experimental XRPD pattern was recorded on a BROKER D5005 diffractometer with Cu Kα radiation (λ = 1.54178 Å).
  • 63
    • 85083139420 scopus 로고    scopus 로고
    • note
    • With a simple tren ligand (i.e. not linked to a hydrophobic cavity), we have not found any report on guest selectivity. Indeed, in the absence of a hydrophobic cavity, the guest binding is very weak and just relies on acid/ base and/or donor/acceptor properties.
  • 64
    • 85083124186 scopus 로고    scopus 로고
    • note
    • 415 However, complexation of a guest with a lipophilic moiety has not been reported. This is obviously due to the smallness of the calix[4]arene cavity that cannot accommodate an organic guest through its narrow rim.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.