Water soluble heterocyclophane as a novel class of inclusion host

Water soluble heterocyclophane as a novel class of inclusion host
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水溶性杂环芳作为一类新型包合主体

DOI:
10.1021/ja00434a069
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发表时间:
1976
影响因子:
15
通讯作者:
Y. Kuroda
Y. Kuroda
中科院分区:
化学1区
文献类型:
--
作者:
I. Tabushi;H. Sasaki;Y. Kuroda

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During the past decade the cyclodextrins have attracted extensive attention as (almost) the sole class of inclusion hosts that form 1: 1 complexes with a variety of hydrophobic guest molecules. 1 Recently, another class of inclusion hosts, the crown family, has been added tothe list, some of whose members exhibit chiral recognition in complexation of both ground and transition states2 and givepromise of interesting and versatile applications to organic chemistry. To further develop and generalize “host-guest” chemistry it is important that still other novel classes of inclusion hosts be studied, and it is to this goal that we are currently investigating polypara-cyclophanes3 and we wish to report here a water soluble het-erocyclophane that strongly binds hydrophobic guests in aqueous solution.The tetrasulfide II was synthesized from xylylene bromide and xylylene dithiol in benzene-ethanol solution and obtained as colorless crystals, mp 199-200 C. II possessed these properties: ir (KBr), 3050, 2950, 1510, 1420, 1230, 1010, 850, 760, 720 cm-1; mass m/e (relativeintensity), 544 (M+, 21), 512 (4), 440 (6), 272 (18), 240 (26), 137 (52), 136 (52), 105 (85), 104 (100). Anal. Found: C, 70.51; H, 5.79. Caled: C, 70.54; H, 5.92. NMR (CDC13), 5 3.55 (singlet, methylene protons 16), 7.18 (singlet, aromatic protons 16 H).