Electrochiroptical systems based on biphenyl-2,2′-diyl-type dicationic dyes: strong chiroptical signals through the transmission of point chirality to axial chirality |
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Authors: | Takanori Suzuki Tomohiro Iwai Eisuke Ohta Hidetoshi Kawai Kenshu Fujiwara |
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Affiliation: | Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | Huge CD amplitude (A = +538) was attained by diastereomeric preference (50% de) for the title dication with two bis[4-(R)-sec-butoxyphenyl]methylium units in benzene at 23 °C. Intramolecular π-π stacking is the origin for effective transmission of point chirality to axial chirality to attain the chiroptical enhancement of 400-times. Thanks to the strong CD signaling, chiroptical changes upon electrolysis could be readily detected, thus realizing a new class of electrochiroptical response systems. Chiroptical properties could also be modified by solvent polarity. |
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Keywords: | Dynamic redox system Hexaphenylethane Chirality Electrochiroptics Chiroptical enhancement |
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