Structure of a Dimeric BINOL-Imine-Zn(II) Complex and Its Role in Enantioselective Fluorescent Recognition
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 st...
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| Veröffentlicht in: | Inorganic chemistry 2020-12, Vol.59 (24), p.17992-17998 |
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| container_issue | 24 |
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| container_title | Inorganic chemistry |
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| creator | Guo, Kai Wang, Ping Tan, Wanli Li, Yan Gao, Xiaowei Wang, Qin Pu, Lin |
| description | 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. |
| doi_str_mv | 10.1021/acs.inorgchem.0c02330 |
| format | Article |
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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. 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Chem</addtitle><date>2020-12-21</date><risdate>2020</risdate><volume>59</volume><issue>24</issue><spage>17992</spage><epage>17998</epage><pages>17992-17998</pages><issn>0020-1669</issn><eissn>1520-510X</eissn><abstract>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. 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| title | Structure of a Dimeric BINOL-Imine-Zn(II) Complex and Its Role in Enantioselective Fluorescent Recognition |
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