Larger Groups, Smaller Enantioselectivity? Two Anthracene-Containing, Pyridino-Crown Ether-Based Fluorescent Sensor Molecules

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2022-08-15 DOI:10.3311/ppch.20468

Balázs Szemenyei, Marianna Firisz, P. Baranyai, Péter Bagi, L. Drahos, Ildikó Móczár, P. Huszthy

引用次数: 1

Abstract

(R,R)- and (S,S)-enantiomers of anthracene-containing pyridino-18-crown-6 ether having tert-butyl groups at the stereogenic centers were prepared with the aim of achieving higher enantioselectivity than for the reported (S,S)-analogue having isobutyl groups. The enantiomeric recognition abilities of the new sensor molecules toward chiral protonated primary amines and amino acid esters were studied in acetonitrile by UV–vis and fluorescence spectroscopies. The pKa values of these pyridino-crown ethers and their reported (S,S)-analogues having methyl or isobutyl groups have also been determined in acetonitrile.

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基团越大，对映体选择性越小?两种含蒽、吡啶冠醚基荧光传感器分子

制备了在立体中心具有叔丁基的含蒽吡啶-18-冠-6醚的(R,R)-和(S,S)-对映体，目的是获得比报道的具有异丁基的(S,S)-类似物更高的对映选择性。用紫外-可见和荧光光谱在乙腈中研究了新型传感器分子对手性质子化伯胺和氨基酸酯的对映体识别能力。这些吡啶冠醚及其报道的具有甲基或异丁基的(S,S)-类似物的pKa值也在乙腈中测定。

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

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.