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Volumn 124, Issue 42, 2002, Pages 12453-12462

Acridinylresorcinol as a self-complementary building block of robust hydrogen-bonded 2D nets with coordinative saturation. Preservation of crystal structures upon guest alteration, guest removal, and host modification

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ADDUCTS;

EID: 0037164009     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026704l     Document Type: Article
Times cited : (89)

References (70)
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    • For the thermodynamic and kinetic analysis of lattice inclusion phenomena, also see: (a) Caira, M. R.; Nassimbeni, L. R.; Toda, F.; Vujovic, D. J. Am. Chem. Soc. 2000, 122, 9367-9372. (b) Caira, M. R.; Nassimbeni, L. R. In Comprehensive Supramolecular Chemistry Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 25. (c) Barbour, L. J.; Caira, M. R.; Nassimbeni, L, R. J. Chem. Soc., Perkin Trans. 2 1993, 2321-2322. (d) Barbour, L. J.; Caira, M. R.; Coetzee, A.; Nassimbeni, L. R. J. Chem. Soc., Perkin Trans. 2 1995, 1345-1349. (e) Caira, M. R.; Home, A.; Nassimbeni, L. R.; Toda, F. Supramol. Chem. 1998, 9, 231-237.
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    • For the thermodynamic and kinetic analysis of lattice inclusion phenomena, also see: (a) Caira, M. R.; Nassimbeni, L. R.; Toda, F.; Vujovic, D. J. Am. Chem. Soc. 2000, 122, 9367-9372. (b) Caira, M. R.; Nassimbeni, L. R. In Comprehensive Supramolecular Chemistry Lehn, J.-M., Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Pergamon Press: Oxford, 1996; Vol. 6, Chapter 25. (c) Barbour, L. J.; Caira, M. R.; Nassimbeni, L, R. J. Chem. Soc., Perkin Trans. 2 1993, 2321-2322. (d) Barbour, L. J.; Caira, M. R.; Coetzee, A.; Nassimbeni, L. R. J. Chem. Soc., Perkin Trans. 2 1995, 1345-1349. (e) Caira, M. R.; Home, A.; Nassimbeni, L. R.; Toda, F. Supramol. Chem. 1998, 9, 231-237.
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    • A preliminary account of a part of this work appeared in the following: Tanaka, T.; Endo, K.; Aoyama, Y. Chem. Lett. 2000. 1424-1425.
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    • note
    • The simplest way to obtain adduct 3·(benzene). although not as single crystals, is to reprecipitate host 3 in methanol upon addition of benzene.
  • 40
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    • note
    • It is interesting to note that the chloroform adduct dipped in benzene undergoes partial guest exchange while maintaining the single crystallinity.
  • 41
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    • note
    • The acridinyl OH group in all of the adducts of host 4 is disordered in two positions, appearing as either 4-OH or 5-OH. The R values become lowest when the occupancy ratios of 0.36:0.64, 0.40:0.60, 0.35:0.65, 0.74:0.26, and 0.82:0.18 are given to adducts 4·(benzene), 4·(chloroform), 4·0.5-(toluene)·0.5(water), 4·(methanol)·(water), and 4·(ethyl acetate), respectively.
  • 42
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    • note
    • Simulation (CrystalStructure Analysis Package, Molecular Structure Corp.) based on the crystal structure of benzene full-adduct 3·(benzene) with a hypothetical occupancy of 0.5 for each benzene molecule in the cavity reproduces the observed powder diffractions of half-adduct 3·0.5(benzene) very well. These results suggest that the single benzene molecule in the cavity of 3·0.5(benzene) is disordered in two locations in a similar manner as in toluene adducts 3·0.5(toluene) and 4·0.5(toluene)·0.5(water)
  • 44
    • 2142762802 scopus 로고    scopus 로고
    • note
    • Small polar molecules such as ethyl acetate and acetone are also guests of half-adduct 3·0.5(benzene) and give Langmuir-type isotherms.
  • 45
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    • note
    • Thermogravimetry indicates that all of the benzene molecules are lost at ≤110°C.
  • 46
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    • note
    • When treated with water, adduct 4·(methanol)·(water) readily affords diaquo adduct 4·2(water).
  • 47
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    • note
    • s = 7.40 Å.
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    • Grignard reactions were carried out according to the procedures shown in ref 27a,b.
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    • For the general procedure of Ullmann reactions, see: Fanta, P. E. Chem. Rev. 1964, 64, 613-632.
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    • On standing, adduct 3·(chloroform) gradually loses some of the included guest molecules.


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