Dynamic Control of Chiral Recognition in Water-Soluble Naphthotubes Induced by Hydrostatic Pressure.

IF 4.8 Q2 NANOSCIENCE & NANOTECHNOLOGY

ACS Nanoscience Au Pub Date : 2024-10-21 eCollection Date: 2024-12-18 DOI:10.1021/acsnanoscienceau.4c00052

Junnosuke Motoori, Tomokazu Kinoshita, Hongxin Chai, Ming-Shuang Li, Song-Meng Wang, Wei Jiang, Gaku Fukuhara

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Abstract

The dynamic control of chiral (enantiomeric) responses in chiral host-guest complexes through external stimuli is a significant challenge in modern chemistry for developing smart stimuli-responsive materials. Herein, we report the (chir)optical properties and chiral recognition behavior of water-soluble chiral naphthotubes (1) under the influence of hydrostatic pressure as an external stimulus. The hydrostatic pressure spectral profiles compared to those obtained at normal pressure revealed the dynamic behavior of 1 under hydrostatic pressure, owing to the flexible linker. In chiral recognition experiments, hydrophilic amino acids such as phenylalanine (Phe) and tryptophan (Trp) exhibited reaction volume changes (ΔV°) of -0.9 cm³ mol^-1 for d-Phe, -1.2 cm³ mol^-1 for l-Phe, -5.6 cm³ mol^-1 for d-Trp, and -7.0 cm³ mol^-1 for l-Trp, with enantioselectivity ranging from 1.2 to 1.6. In contrast, hydrophobic chiral styrene oxide (2) showed ΔV° values of 1.5 cm³ mol^-1 for R-2 and 3.5 cm³ mol^-1 for S- 2, with a relatively higher enantioselectivity of up to 7.6. These contrasting effects of hydrostatic pressure primarily originate from the dynamics of chiral naphthotubes.

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静水压力诱导水溶性萘管手性识别的动态控制。

通过外部刺激对手性主客体复合物的手性（对映体）反应进行动态控制是现代化学中开发智能刺激响应材料的一个重大挑战。本文报道了在静水压力作用下水溶性手性萘管(1)的光学性质和手性识别行为。与常压下得到的静水压力谱曲线相比，由于柔性接头的存在，静水压力谱显示了1在静水压力下的动态特性。在手性识别实验中，苯基丙氨酸（Phe）和色氨酸（Trp）等亲水性氨基酸的反应体积变化（ΔV°）为：d-Phe为-0.9 cm3 mol-1， l-Phe为-1.2 cm3 mol-1， d-Trp为-5.6 cm3 mol-1， l-Trp为-7.0 cm3 mol-1，对映选择性范围为1.2 ~ 1.6。疏水手性氧化苯乙烯(2)的R-2的ΔV°值为1.5 cm3 mol-1， S- 2的ΔV°值为3.5 cm3 mol-1，对映体选择性相对较高，可达7.6。静水压力的这些对比效应主要来源于手性萘管的动力学。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

ACS Nanoscience Au 材料科学、纳米科学-

CiteScore

4.20

自引率

0.00%

发文量

期刊介绍： ACS Nanoscience Au is an open access journal that publishes original fundamental and applied research on nanoscience and nanotechnology research at the interfaces of chemistry biology medicine materials science physics and engineering.The journal publishes short letters comprehensive articles reviews and perspectives on all aspects of nanoscience and nanotechnology:synthesis assembly characterization theory modeling and simulation of nanostructures nanomaterials and nanoscale devicesdesign fabrication and applications of organic inorganic polymer hybrid and biological nanostructuresexperimental and theoretical studies of nanoscale chemical physical and biological phenomenamethods and tools for nanoscience and nanotechnologyself- and directed-assemblyzero- one- and two-dimensional materialsnanostructures and nano-engineered devices with advanced performancenanobiotechnologynanomedicine and nanotoxicologyACS Nanoscience Au also publishes original experimental and theoretical research of an applied nature that integrates knowledge in the areas of materials engineering physics bioscience and chemistry into important applications of nanomaterials.