Helic[1]triptycene[3]arene: Synthesis, Complexation, and Formation of [2]Rotaxane Shuttle.,The Journal of Organic Chemistry

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Helic[1]triptycene[3]arene: Synthesis, Complexation, and Formation of [2]Rotaxane Shuttle.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-08-14 , DOI: 10.1021/acs.joc.0c01558
Jing Li _{1,

2} , Xiao-Ni Han _{1,

2} , He-Ye Zhou _{1,

2} , Ying Han ₁ , Chuan-Feng Chen _{1,

2}

Affiliation

A new macrocyclic arene, helic[1]triptycene[3]arene H, was conveniently synthesized in 37% yield by a one-pot reaction starting from 2,6-dimethoxyl-3,7-dihydroxymethyltriptycene. Macrocycle H showed fixed conformation in solution and could form 1:1 complexes with a series of neutral guests, secondary ammonium salts, and tertiary ammonium salts in both solution and solid states. The association constants between H and the neutral guests were between (1.23 ± 0.10) × 10² and (4.70 ± 0.47) × 10³ M^–1, while the association constants between H and the ammonium guests were between (1.35 ± 0.12) × 10³ and (1.59 ± 0.14) × 10⁵ M^–1. Moreover, H showed bigger association constants with secondary ammonium salts than those with tertiary ammonium salts possibly because of the steric hindrance effect and multiple intermolecular interactions. The stimuli-responsive complexation between H and the ammonium salts could be controlled by the addition and removal of acids and bases as well. Based on the host–guest complexation between H and the secondary ammonium salt, [2]rotaxane was further synthesized, and its shuttling motion could be efficiently controlled by an acid and base.

中文翻译：

螺旋[1]三茂[3]芳烃：[2]轮烷的穿梭反应的合成，络合和形成。

通过从2，6-二甲氧基-1，3，7-二羟基甲基三茂苯开始的一锅反应，以37％的收率方便地合成了一种新的大环芳烃，螺旋[1]三茂[3]芳烃H。大环H在溶液中显示出固定的构象，并可以与一系列中性客体，仲铵盐和叔铵盐在溶液和固态下形成1：1的络合物。H和中性客体之间的缔合常数在（1.23±0.10）×10 ²和（4.70±0.47）×10 ³ M ^–1之间，而H和铵客体之间的缔合常数在（1.35±0.12）× 10 ³和（1.59±0.14）×10 ⁵M ^–1。此外，H显示出与仲铵盐相比具有比叔铵盐更大的缔合常数，这可能是由于空间位阻效应和多种分子间相互作用。H和铵盐之间的刺激响应络合物也可以通过添加和去除酸和碱来控制。基于H和仲铵盐之间的主客体络合作用，进一步合成了[2]轮烷，其穿梭运动可以通过酸和碱有效控制。

更新日期：2020-09-05

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