Thinking Outside the Blue Box: Induced Fit Within a Unique Self-assembled Polycationic Cyclophane,Journal of the American Chemical Society

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Thinking Outside the Blue Box: Induced Fit Within a Unique Self-assembled Polycationic Cyclophane
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2019-02-07 , DOI: 10.1021/jacs.8b12599
Arturo Blanco-Gómez ₁ , Ángel Fernández-Blanco ₁ , Víctor Blanco ₂ , Jaime Rodríguez ₁ , Carlos Peinador ₁ , Marcos D García ₁

Affiliation

We present herein the development of a new polycationic molecular receptor, inspired by the ubiquitous cyclobis(paraquat- p-phenylene)cyclophane ("blue box"). Our analogue, the "white box", has been easily self-assembled on a preparative scale in water, using a template-assisted process by acyl hydrazone bonding of complementary bis(pyridinium)xylylene tweezers, followed by kinetic trapping of the empty receptor. The obtained macrocycle was found to display a marked pH responsiveness in water, because of an abnormal acidity of the amide protons within its structure. Consequently, and because of the concurrence of rotational isomerism under acidic conditions (fixed at higher pH values), the compound was found to display a dual behavior as a conformationally locked/flexible molecular host, being able to recognize appropriate aromatic substrates, in a lock and key or induced fit fashion, by a conjunction of π-π, C-H···π, and, crucially, the hydrophobic effect.

中文翻译：

跳出蓝框思考：在独特的自组装聚阳离子环磷中诱导契合

我们在此介绍了一种新的聚阳离子分子受体的开发，其灵感来自无处不在的环双（百草枯-对亚苯基）环烷（“蓝盒”）。我们的类似物“白盒”已经很容易在水中以制备规模自组装，使用模板辅助过程通过互补双（吡啶鎓）二甲苯镊子的酰基腙键合，然后是空受体的动力学捕获。发现获得的大环在水中表现出显着的 pH 响应性，因为其结构内的酰胺质子具有异常酸度。因此，由于在酸性条件下（固定在较高的 pH 值）下同时发生旋转异构现象，发现该化合物作为构象锁定/柔性分子宿主表现出双重行为，

更新日期：2019-02-07

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