Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 12518-12522 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 41 |
| DOIs | |
| Publication status | Published - Jan 1 2017 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
Cite this
A Chiral Recognition System Orchestrated by Self-Assembly : Molecular Chirality, Self-Assembly Morphology, and Fluorescence Response. / Noguchi, Takao; Roy, Bappaditya; Yoshihara, Daisuke; Sakamoto, Junji; Yamamoto, Tatsuhiro; Shinkai, Seiji.
In: Angewandte Chemie - International Edition, Vol. 56, No. 41, 01.01.2017, p. 12518-12522.Research output: Contribution to journal › Article
}
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
PY - 2017/1/1
Y1 - 2017/1/1
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.
UR - http://www.scopus.com/inward/record.url?scp=85028547633&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85028547633&partnerID=8YFLogxK
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 -