TY - JOUR
T1 - A Chiral Recognition System Orchestrated by Self-Assembly
T2 - Molecular Chirality, Self-Assembly Morphology, and Fluorescence Response
AU - Noguchi, Takao
AU - Roy, Bappaditya
AU - Yoshihara, Daisuke
AU - Sakamoto, Junji
AU - Yamamoto, Tatsuhiro
AU - Shinkai, Seiji
N1 - Funding Information:
We are grateful for one Reviewer who raised a few constructive comments on the further applicability of this system. This work was supported by JSPS KAKENHI Grant Number JP16K17937 (Grant-in-Aid for Young Scientists (B)). The measurement of 1H and 13C NMR spectroscopy and MALDI-TOF MS was made at the Analytical Center in Fukuoka Industry-academia Symphonicity. The measurement of HRMS was performed using JEOL JMS700 at the Evaluation Center of Materials Properties and Function, Institute for Materials Chemistry and Engineering, Kyushu University.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/10/2
Y1 - 2017/10/2
N2 - The newly developed oligophenylenevinylene (OPV)-based fluorescent (FL) chiral chemosensor (OPV-Me) for the representative enantiomeric guest, 1,2-cyclohexanedicarboxylic acid (1,2-CHDA: RR- and SS-form) showed the high chiral discrimination ability, resulting in the different aggregation modes of OPV-Me self-assembly: RR-CHDA directed the fibrous supramolecular aggregate, whereas SS-CHDA directed the finite aggregate. The consequent FL intensity toward RR-CHDA was up to 30 times larger than that toward SS-CHDA. Accordingly, highly enantioselective recognition was achieved. Application to the chirality sensing was also possible: OPV-Me exhibited a linear relationship between the FL intensity and the enantiomeric excess through the morphological development of stereocomplex aggregates. These results clearly show that the chiral recognition ability is manifested by the amplification cascade of the chirality difference through self-assembly.
AB - The newly developed oligophenylenevinylene (OPV)-based fluorescent (FL) chiral chemosensor (OPV-Me) for the representative enantiomeric guest, 1,2-cyclohexanedicarboxylic acid (1,2-CHDA: RR- and SS-form) showed the high chiral discrimination ability, resulting in the different aggregation modes of OPV-Me self-assembly: RR-CHDA directed the fibrous supramolecular aggregate, whereas SS-CHDA directed the finite aggregate. The consequent FL intensity toward RR-CHDA was up to 30 times larger than that toward SS-CHDA. Accordingly, highly enantioselective recognition was achieved. Application to the chirality sensing was also possible: OPV-Me exhibited a linear relationship between the FL intensity and the enantiomeric excess through the morphological development of stereocomplex aggregates. These results clearly show that the chiral recognition ability is manifested by the amplification cascade of the chirality difference through self-assembly.
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U2 - 10.1002/anie.201706142
DO - 10.1002/anie.201706142
M3 - Article
C2 - 28749601
AN - SCOPUS:85028547633
VL - 56
SP - 12518
EP - 12522
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 41
ER -