Induced Helical Chirality of Perylenebisimide Aggregates Allows for Enantiopurity Determination and Differentiation of α‐Hydroxy Carboxylates by Using Circular Dichroism |
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Authors: | Xin Wu Xuan‐Xuan Chen Bing‐Nan Song Dr. Yan‐Jun Huang Prof. Dr. Zhao Li Zhan Chen Prof. Dr. Tony D. James Prof. Dr. Yun‐Bao Jiang |
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Affiliation: | 1. Department of Chemistry, College of Chemistry and Chemical Engineering the MOE Key Laboratory of Spectrochemical Analysis and Instrumentation and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Xiamen University, Xiamen 361005 (P.R. China);2. Department of Chemistry, University of Bath, Bath BA2 7AY (UK) |
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Abstract: | We have developed a working strategy for accurate enantiomeric excess (ee) determination based on induced helical aggregation of achiral perylenebisimide (PBI) dyes. PBI dyes functionalized with boronic acid moieties were shown to be effective chirality sensors for α‐hydroxy carboxylates. Seven α‐hydroxy carboxylates tested showed strong induced Cotton effects in the perylene absorption region around λ=500 nm, which were utilized for enantiomeric excess determination and chemo‐discrimination of the analytes, with an average absolute error of 2 % in ee determination and 100 % correctness in analyte classification. Responses in the absorption spectra, which arise from the guest‐enhanced aggregation, allow the determination of the sample concentration, thus enabling analysis of samples of unknown concentration and ee. The simplicity of the strategy, the ease of sample preparation, and the accuracy demonstrated, can potentially facilitate screening procedures in asymmetric synthesis. |
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Keywords: | chirality circular dichroism dyes/pigments hydroxyl acid polymers supramolecular chemistry |
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