Journal
INORGANIC CHEMISTRY
Volume 59, Issue 24, Pages 17992-17998Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.inorgchem.0c02330
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Funding
- U.S. National Science Foundation [CHE-1855443]
- Sichuan Science and Technology Program [2019JDTD0016]
- State Scholarship Fund from China Scholarship Council [201708510004]
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A pyridine containing BINOL-based aldehyde (S)- or (R)-4 is found to show highly enantioselective fluorescent response toward phenylglycinol in the presence of Zn2+. A chirality matched dimeric BINOL-imine-Zn(II) complex is isolated from the reaction of (S)-4 with L-phenylglycinol and Zn2+ whose structure is established by X-ray analysis. Comparison of the structure of this SS-complex with a molecular modeling structure of the chirality mismatched SR-complex generated from the reaction of (S)-4 with D-phenylglycinol has provided important insight into the origin of the observed highly enantioselective fluorescent response. It is found that the solvent-accessible surface area of the chirality-matched SS-complex is much smaller than that of the chirality mismatched SR-complex, which gives the more tightly packed and structurally rigid SS-complex with greatly enhanced fluorescence.
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