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Induced Helical Chirality of Perylenebisimide Aggregates Allows for Enantiopurity Determination and Differentiation of α‐Hydroxy Carboxylates by Using Circular Dichroism
Author(s) -
Wu Xin,
Chen XuanXuan,
Song BingNan,
Huang YanJun,
Li Zhao,
Chen Zhan,
James Tony D.,
Jiang YunBao
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402627
Subject(s) - analyte , circular dichroism , chirality (physics) , chemistry , enantiomer , enantiomeric excess , absorption (acoustics) , boronic acid , chromatography , analytical chemistry (journal) , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , materials science , catalysis , nambu–jona lasinio model , composite material , chiral symmetry breaking , physics , quantum mechanics , quark
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.