Bulletin of the Korean Chemical Society

  • 제25권11호
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  • Pages.1635-1640
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  • 2004
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Synthesis and Guest Binding Properties of Cyclophanes Containing Two Benzo[b]furan Rings

  • 발행 : 2004.11.20
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초록

The cyclophanes 1a-d containing two benzo[b]furan rings connected by various bridges have been prepared and their binding behaviors with N-benzylphenethylammonium cation 2 were examined by NMR titration method. The successive alkylation reactions of 4-hydroxyl groups and then 2-hydroxyl groups of 2,4-dihydroxybenzophenonse gave macrocycles 5a-c. Photoirradiation of the macrocycles 5a-c with 350 nm mercury lamp followed by dehydration afforded the cyclophanes 1a-c. Hydrolysis of two ester groups pendant on a bridge of 1b produced the carboxyl group-containing cyclophane 1d. The cyclophane 1a having a p-xylene bridge showed 1 : 1 binding with 2 with the binding constant of $36{\pm}6M^{-1}$ in 3 : 1 $CDCl_3$/methanol-$d_4$ solvent, while 1b and 1c which have neutral flexible bridges exhibited no appreciable binding with 2. The disodium salt of 1d showed much higher binding affinity for 2 forming 1 : 1 and 1 : 2 complexes.

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참고문헌

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피인용 문헌

  1. 1,5-And 1,3-Photocyclization Reactions Of 8-Substituted- 1,2,3,4-Tetrahydro-1-Naphthalenones vol.15, pp.5, 2009, https://doi.org/10.1515/HC.2009.15.5.369
  2. Synthesis and Guest Binding Properties of Cyclophanes Containing Two Benzo[b]furan Rings. vol.36, pp.13, 2005, https://doi.org/10.1002/chin.200513063