A double concave hydrocarbon buckycatcher.

A double concave hydrocarbon buckycatcher.
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DOI:
10.1021/ja070616p
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发表时间:
2007-03
影响因子:
15
通讯作者:
A. Sygula;F. Fronczek;R. Sygula;P. W. Rabideau;M. Olmstead
A. Sygula;F. Fronczek;R. Sygula;P. W. Rabideau;M. Olmstead
中科院分区:
化学1区
文献类型:
--
作者:
A. Sygula;F. Fronczek;R. Sygula;P. W. Rabideau;M. Olmstead

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双Diels −桤木加成将异corannulenofurane与二苯并环辛二炔反应,然后脱氧,得到一个分子钳C60 H28,带有两个corannulene钳和一个四苯并环辛四烯链。X射线晶体结构测定其包合物与巴克敏斯特富勒烯C60提供了实验证据的重要性,有吸引力的凹凸π-π相互作用的超分子化学的富勒烯与巴基碗。用NMR滴定法测定了配合物的缔合常数为8600 ± 500 M-1。
Double Diels−Alder addition of isocorannulenofuran to dibenzocyclooctadiyne followed by deoxygenation produces a molecular tweezers C60H28 with two corannulene pincers and a tetrabenzocyclooctatetraene tether. X-ray crystal structure determination of its inclusion complex with buckminsterfullerene C60 provides experimental evidence for the importance of attractive concave−convex π−π interactions in the supramolecular chemistry of fullerenes with buckybowls. An association constant of 8600 ± 500 M-1 was estimated for the complex formation by NMR titration experiment in toluene-d8.