Design, Synthesis and Optical Properties of a New Type of Chiral Molecular Square with Double Helical Structure

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Design, Synthesis and Optical Properties of a New Type of Chiral Molecular Square with Double Helical Structure

AN De-Lie, ZHANG Ying-Jun, CHEN Qiang, ZHANG Zhi-Yang, YAN Hong, MENG Gui-Ying, CHEN Yan-Gui, ZHAO Wen-Ying, YU Zheng-Ying

College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

Received:2005-12-05 Revised:1900-01-01 Online:2006-12-10 Published:2006-12-10
Contact: AN De-Lie

Abstract

Abstract: (R)- and (S)-2,2'-diethynyl-1,1'-binaphthyl with highly stable chiral configurations were used as the structural templates and linking bridges, and a new type of chiral molecular square with helical structure (R,R,R,R)-1 and (S,S,S,S)-1 were synthesized in enantiopure form via four steps including the introduction of protecting-group, intermolecular coupling reaction, removal of protecting group, and intermolecular cross-coupling cyclyzation. Compound 1 was characterized by MS, IR, ¹H and ¹³C NMR as well as elemental analysis. The specific rotations([α]²⁵_D) of the two isomers in CH₂Cl₂ are +887.3° and -889.7°, respectively, and their circular dichroism(CD) spectra represented exactly the mirror images of each other. These results reflected unambiguously enantiomeric relationship between the two isomers.

Key words: Chirality, Binaphthyls template, Linking bridge, Helical structure, Molecular square, Synthesis

CLC Number:

O624

TrendMD:

AN De-Lie, ZHANG Ying-Jun, CHEN Qiang, ZHANG Zhi-Yang, YAN Hong, MENG Gui-Ying, CHEN Yan-Gui, ZHAO Wen-Ying, YU Zheng-Ying. Design, Synthesis and Optical Properties of a New Type of Chiral Molecular Square with Double Helical Structure[J]. Chem. J. Chinese Universities, doi: .

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Design, Synthesis and Optical Properties of a New Type of Chiral Molecular Square with Double Helical Structure

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