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Colorimetric Sensing of Chirality Based on Synergistic Effect of Multiple Chiral Amide Receptors Consecutively Organized along Poly(phenylacetylene) Backbone
Macromolecules ( IF 5.1 ) Pub Date : 2024-12-10 , DOI: 10.1021/acs.macromol.4c01800
Ryosuke Sakai, Yoshinobu Mato, Hokuto Ishimaru, Keisuke Ogata, Shota Kurose, Shun Ozawa, Satoshi Umeda, Katsuyuki Tsuda, Toshifumi Satoh, Toyoji Kakuchi

Despite the increasing demand for simple, rapid, and convenient chirality-sensing methods, the development of reliable and practical colorimetric sensors for chirality assays remains challenging. In this study, we investigated the applicability of poly(phenylacetylene) with chiral amide receptors derived from l-phenylalanine (PPAPhe) to such chiral sensors. The various advantages of PPAPhe as a chiral sensor, including its immediate colorimetric response upon the addition of chiral amino acids and the large chirality-selective color difference between the d- and l-enantiomers, validate its potential as a colorimetric probe for both qualitative and quantitative analyses of chirality. To elucidate the excellent enantioselective color-differentiating ability of PPAPhe, its colorimetric response was compared with that of several model compounds: the monomer containing a single chiral receptor, statistical copolymers with almost randomly distributed chiral receptor units, and block copolymers bearing a segment composed of consecutive receptor units. A detailed examination revealed that a contiguous sequence of multiple chiral receptor units is indispensable for the chirality-selective colorimetric response of PPAPhe. In addition, the findings of this study further indicate the possibility that the organization of multiple receptor units along a polymer backbone could impart highly enhanced and improved chiral recognition ability, even though the receptor itself possesses insufficient and minute chiral recognition ability. As an example of further applications, PPAPhe was verified to be capable of colorimetric chiral sensing of chiral drugs.

中文翻译:


基于沿聚(苯乙炔)骨架连续组织的多个手性酰胺受体的协同作用的手性比色传感



尽管对简单、快速和方便的手性传感方法的需求不断增长,但用于手性测定的可靠且实用的比色传感器的开发仍然具有挑战性。在这项研究中,我们调查了聚苯乙炔与源自 l-苯丙氨酸 (PPAPhe) 的手性酰胺受体对此类手性传感器的适用性。PPAPhe 作为手性传感器的各种优点,包括添加手性氨基酸后的即时比色响应以及 d-和 l-对映异构体之间的大手性选择性色差,验证了其作为比色探针用于手性定性和定量分析的潜力。为了阐明 PPAPhe 优异的对映选择性颜色区分能力,将其比色响应与几种模型化合物的比色响应进行了比较:包含单个手性受体的单体、具有几乎随机分布的手性受体单元的统计共聚物以及带有由连续受体单元组成的片段的嵌段共聚物。详细检查表明,多个手性受体单元的连续序列对于 PPAPhe 的手性选择性比色反应是必不可少的。此外,本研究的结果进一步表明,即使受体本身具有不足和微小的手性识别能力,沿聚合物骨架组织多个受体单元的组织也可以赋予高度增强和改进的手性识别能力。作为进一步应用的一个例子,PPAPhe 被验证能够对手性药物进行比色手性传感。
更新日期:2024-12-10
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