TY - JOUR
T1 - Induced helical chirality of perylenebisimide aggregates allows for enantiopurity determination and differentiation of α-hydroxy carboxylates by using circular dichroism
AU - Wu, X.
AU - Chen, X.-X.
AU - Song, B.-N.
AU - Huang, Y.-J.
AU - Li, Z.
AU - Chen, Z.
AU - James, T.D.
AU - Jiang, Y.-B.
PY - 2014/9/8
Y1 - 2014/9/8
N2 - 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=500nm, 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.
AB - 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=500nm, 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.
UR - http://www.scopus.com/inward/record.url?scp=84905294751&partnerID=8YFLogxK
UR - http://dx.doi.org/10.1002/chem.201402627
U2 - 10.1002/chem.201402627
DO - 10.1002/chem.201402627
M3 - Article
SN - 0947-6539
VL - 20
SP - 11793
EP - 11799
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 37
ER -