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首页> 外文期刊>Chemistry: A European journal >Triptycene-derived calix [6]arenes: Synthesis, structures, and their complexation with fullerenes C_(60)and C_(70)
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Triptycene-derived calix [6]arenes: Synthesis, structures, and their complexation with fullerenes C_(60)and C_(70)

机译：三萜烯衍生的杯[6]芳烃：合成，结构及其与富勒烯C_（60）和C_（70）的络合

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摘要

Two pairs of novel triptycene-derived calix[6]arenes 4a, b and 5a, b have been efficiently synthesized through both one-pot and two-step fragment-coupling strategies starting from 2,7-bis(hydroxymethyl)-l,8-dimethoxytriptycene 1. Subsequent demethylation of 4a.b and 5a,b with BBr_3 in dry dichloromethane gave the macrocyclic compounds 6a,b and 7a,b. Treatment of either 4a or 6a with AlCl_3 resulted in the same debutylated product 8, while 9 was similarly obtained from either 5 a or 7 a. Structural studies revealed that all of the macrocycles have well-defined structures with fixed conformations both in solution and in the solid state owing to the introduction of the triptycene moiety with a rigid three-dimensional (3D) structure, making them very different from their classical calix [6]arene counterparts. As a consequence, it was found that all of these the triptycene-derived calix [6]arenes could encapsulate small neutral molecules in their cavities in the solid state. Moreover, it was also found that the macrocycles 4 b and 5 b showed highly efficient complexation abilities toward fullerenes C_(60) and C_(70), forming 1:1 complexes with association constants ranging from (5.22 ± 0.20) × 10_4 to(8.68±0.30)×l0 ~4M~(-1).
机译：从2,7-双（羟甲基）-1,8开始，通过一锅法和两步片段偶联策略，已经有效地合成了两对新颖的三萜烯杯[6]芳烃4a，b和5a，b。 -二甲氧基三茂铁1.随后在干燥的二氯甲烷中用BBr_3将4a.b和5a，b脱甲基，得到大环化合物6a，b和7a，b。用AlCl 3处理4a或6a得到相同的脱丁基产物8，而类似地从5a或7a获得9。结构研究表明，由于引入了具有刚性三维（3D）结构的三并茂结构部分，所有大环在溶液和固态中均具有定义明确的结构，具有固定的构象，这使其与经典结构大为不同杯[6]芳烃同行。结果，发现所有这些三萜烯衍生的杯芳烃[6]芳烃都可以在其空腔中将固态的小中性分子包裹起来。此外，还发现大环4b和5b对富勒烯C_（60）和C_（70）表现出高效的络合能力，形成1：1络合物，缔合常数范围为（5.22±0.20）×10_4至（ 8.68±0.30）×l0〜4M〜（-1）。

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