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首页> 外文期刊>Chemistry: A European journal >Assembly of water-soluble, dynamic, covalent container molecules and their application in the room-temperature stabilization of protoadamantene
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Assembly of water-soluble, dynamic, covalent container molecules and their application in the room-temperature stabilization of protoadamantene

机译：水溶性，动态，共价容器分子的组装及其在原金刚烷室温稳定中的应用

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The thermodynamically controlled reactions of water-soluble tetraformylcavitand 2 with two equivalents of H _2N(CH _2) _nNH _2 (n=2-4) in the presence of a suitable templating guest give hemicarceplexes 1 a-c·guest, the yield of which depends on the match between size and shape of the guest and that of the inner phase. These hemicarceplexes are dynamic and dissociate upon addition of acid and reform upon basification. In water, they exchange guests through temporary hydrolysis of imine bonds. To test 1 b as molecular reaction flask, 3-noradamantyldiazirine 6 was encapsulated and photolyzed at 350 nm to produce Bredt olefin protoadamantene 5 and 1-noradamantyldiazomethane 8 in a 4:1 ratio. Encapsulated protoadamantene is stable for days at room temperature in (CD _3) _2SO/CD _3CN (t _(1/2)=5.5 days) and has a lifetime of several minutes in D _2O. Molecular nanoflask! Room-temperature stabilization of protoadamantene was achieved inside a water-soluble, dynamic, covalent, hemicarcerand nanoflask. The nanoflask spontaneously assembles from a cavitand and propylenediamine in water in the presence of 3-noradamantyldiazirine as a template (see scheme). Photolysis of the imprisoned diazirine yields the Bredt olefin, which survives for days at room temperature.
机译：在合适的模板客体存在下，水溶性四甲酰基cavitand 2与两个当量的H _2N（CH _2）_nNH _2（n = 2-4）进行热力学控制的反应得到半拱骨架1 ac·guest，其产率取决于客体和内相的大小和形状之间的匹配。这些半拱状复合物是动态的，在添加酸时会解离，在碱化时会重新形成。在水中，它们通过亚胺键的暂时水解来交换客人。为了测试1b作为分子反应烧瓶，将3-正金刚烷基重氮基6封装并在350nm下光解以产生4：1比例的Bredt烯烃原金刚烷5和1-正金刚烷基重氮甲烷8。封装的金刚烷在室温下在（CD _3）_2SO / CD _3CN中稳定几天（t _（1/2）= 5.5天），在D _2O中的寿命为几分钟。分子纳米瓶！原金刚烷在室温下稳定在水溶性，动态，共价，半焦和纳米烧瓶中。在存在3-去甲金刚烷基重氮作为模板的情况下，纳米烧瓶自空化体和丙二胺在水中自发组装（参见方案）。囚禁的二嗪胺的光解产生了Bredt烯烃，该烯烃在室温下可存活数天。

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