Stereoselective synthesis and higher-order derivatization of planar chiral cyclophanes

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This syntheses of C_2-symmetric enantiomerically pure polyparacyclophane derivatives were achieved by Suzuki-Miyaura coupling method, where the synthesis of these C_2 -symmetrical paracyclophanes was based on the hydrogen-bond controlling strategy by using styryl sulfoxide derivatives. Bistriflates, derived from dihydroquinone derivative of monomeric cyclophanes, were used as building blocks for their oligomer synthesis. Incorporation of phenyl spacer to sustain π-conjugation was successful, giving a heptaphenylene derivative. The structure was confirmed by single crystal X-ray analysis, revealing its linear structure. UV-vis and CD spectra of the compound suggested a helical conformation of thepolyphenylene skeleton in organic solvents, such as chloroform.