Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts

Zhang Y-F, Cao X-P, Chow H-F, Kuck D (2017)
JOURNAL OF ORGANIC CHEMISTRY 82(1): 179-187.

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Two tribenzotriquinacene-based crown ethers, TBTQdibenio-24-crown-8 5 and-TBTQbenzo-21-crOwn-7 6, were prepared from the key TBTQ intermediate, 2,3-dihydroxy-4b,8b,12b,12d-tetramethyltribenzotriquinacene (13), which in turn was synthesized in six steps using two variants of our cyclodehydration method on a multigrarri scale. The host-guest complexation properties of the TBTQbased crown ethers 5 and 6 With a pataquat derivative, 16, and two secondary ammonium salts, 17 and 18, were studied by H-1 NMR spectroscopy and mass spectrometry. It was found that host 5 binds to the paraquat deriVative 16 as a 1:1 complex in CDCl3/CD3CN solution with an association constant K-a = (9.2 +/- 1.8) X 10(2) M-1, whereas no complexation was found for 17 and 18. In contrast, the TBTQcrown ether 6 assembles selectively with dibutylammonium hexafluorophosphate 18 as a 1:1 complex in CDCl3/CD3COCD3 [K-a = (5.0 +/- 1.4) X 10(2) M-1]; for which a threaded [2]pseudorotaxane structure is assumed.
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Zhang Y-F, Cao X-P, Chow H-F, Kuck D. Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts. JOURNAL OF ORGANIC CHEMISTRY. 2017;82(1):179-187.
Zhang, Y. - F., Cao, X. - P., Chow, H. - F., & Kuck, D. (2017). Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts. JOURNAL OF ORGANIC CHEMISTRY, 82(1), 179-187. doi:10.1021/acs.joc.6b02326
Zhang, Y. - F., Cao, X. - P., Chow, H. - F., and Kuck, D. (2017). Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts. JOURNAL OF ORGANIC CHEMISTRY 82, 179-187.
Zhang, Y.-F., et al., 2017. Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts. JOURNAL OF ORGANIC CHEMISTRY, 82(1), p 179-187.
Y.-F. Zhang, et al., “Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts”, JOURNAL OF ORGANIC CHEMISTRY, vol. 82, 2017, pp. 179-187.
Zhang, Y.-F., Cao, X.-P., Chow, H.-F., Kuck, D.: Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts. JOURNAL OF ORGANIC CHEMISTRY. 82, 179-187 (2017).
Zhang, Yu-Fei, Cao, Xiao-Ping, Chow, Hak-Fun, and Kuck, Dietmar. “Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts”. JOURNAL OF ORGANIC CHEMISTRY 82.1 (2017): 179-187.
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