Liquid-crystalline mesogens based on cyclo[6]aramides: distinctive phase transitions in response to macrocyclic host-guest interactions

Angewandte Chemie
Xiaowei LiLihua Yuan

Abstract

Producing macrocyclic mesogens that are responsive to guest encapsulation presents a significant challenge. Cyclo[6]aramides, a type of macrocycle with a hydrogen-bond-constrained backbone, exhibit thermotropic lamellar, discotic nematic, hexagonal, and rectangular columnar mesophases over a considerably wide temperature range, including at room temperature. Additionally, cyclo[6]aramides show unusual mesophase transitions from lamellar to hexagonal columnar phase mediated by macrocyclic host-guest (H-G) interactions between the macrocycles and alkylammonium salts. The phase transition, triggered by an organic guest engaging in H-G interactions with a macrocyclic cavity, provides a novel strategy for manipulating the properties of liquid-crystalline materials. The crystal structure of a homologous cyclo[6]aramide reveals a disk-shaped, near-planar molecular backbone that facilitates intermolecular π-π stacking and leads to columnar assembly.

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Citations

Dec 20, 2015·Journal of the American Chemical Society·Hae-Geun JeonKyu-Sung Jeong
Mar 26, 2016·Journal of the American Chemical Society·Yun LiuAmar H Flood
Feb 18, 2018·Chemistry, an Asian Journal·Hongyan WangYulan Chen
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Jul 20, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Xuebin WangLihua Yuan
Mar 12, 2020·Journal of the American Chemical Society·Yi-Xiong HuHai-Bo Yang
Apr 6, 2017·Organic Letters·Huaiqing ZhaoHuaqiang Zeng

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