Tribenzotriquinacene-Based Crown Ethers: Synthesis and Selective Complexation with Ammonium Salts
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https://figshare.com/articles/dataset/Tribenzotriquinacene-Based_Crown_Ethers_Synthesis_and_Selective_Complexation_with_Ammonium_Salts/4300184
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资源简介：
Two tribenzotriquinacene-based
crown ethers, TBTQ-dibenzo-24-crown-8 5 and TBTQ-benzo-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 multigram scale.
The host–guest complexation properties of the TBTQ-based crown
ethers 5 and 6 with a paraquat derivative, 16, and two secondary ammonium salts, 17 and 18, were studied by 1H 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 of Ka = (9.2 ± 1.8) × 102 M–1, whereas no complexation was found for 17 and 18. In contrast, the TBTQ-crown ether 6 assembles
selectively with dibutylammonium hexafluorophosphate 18 as a 1:1 complex in CDCl3/CD3COCD3 [Ka = (5.0 ± 1.4) × 102 M–1], for which a threaded [2]pseudorotaxane
structure is assumed.
创建时间：
2016-12-09
