Inclusion complex formation of tetra(p-halophenyl)ethylenes with halogenated guest compounds through halogen–halogen interaction

Author:

Tanaka Koichi,Fujimoto Daisuke,Toda Fumio

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference9 articles.

1. Solid-State Supramolecular Chemistry: Crystal Engineering in Comprehensive Supramolecular Chemistry; MacNicol, D. D.; Toda, F.; Bishop, R., Eds.; Pergamon: Oxford, 1996; Vol. 6.

2. Johnson, L. V.; Smith, F.; Stacey, M.; Tatlow, J. C. J. Chem. Soc. 1952, 4710.

3. Bethell, D.; Callister, J. D. J. Chem. Soc. 1963, 3801.

4. Tanaka, K.; Fujimoto, D.; Oeser, T.; Irngartinger, H.; Toda, F. Chem. Commun. 2000, 413.

5. Host compound 1e was prepared as follows: A suspension of tertraphenylethylene (1a, 8.3 g, 25 mmol), iodine (12.7 g, 50.0 mmol) and bis[trifluoroacetoxy]phenyliodine (26.2 g, 60 mmol) in CHCl3 (30 ml) was stirred at room temperature. After the iodine color disappeared, the reaction mixture was filtered, washed with a little hexane, dried and recrystallized from toluene to give 1e as colorless prisms (20.9 g, 76% yield). Mp: 284–287°C; UV(CHCl3): λ nm (ε) 270 (162000), 320 (23800); 1H NMR (CDCl3): δ 7.46 (8H, d, J=8.4 Hz, Ar), 6.70 (8H, d, J=8.4 Hz, Ar); anal. found: C, 37.66%; H, 2.08%. Calcd. for C26H16I4: C, 37.35%; H, 1.93%

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