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Multiply Twisted Chiral Macrocycles Clamped by Tethered Binaphthyls Leading to High Circularly Polarized Luminescence Brightness

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Chiral macrocyclic dimers, trimers, and tetramers composed of paraphenylene and tethered binaphthyl were synthesized, and their molecular structures and chiroptical properties were investigated. X-ray analysis and theoretical calculations revealed that multiple twisted molecular structures—dimer, trimer, and tetramer—adopt figure-eight, Möbius triangle, and concave rectangle, respectively. These homologues provide large e values in their absorption spectra because of the π-conjugation of the naphthalene-phenylene-naphthalene frameworks. Owing to the shape-persistent ring structure and tethering with -OCH 2 CH 2 O-, high fluorescence quantum yields and a relatively high dissymmetry factor g CPL in circularly polarized luminescence (CPL) spectra were achieved. This results in CPL brightness ( B CPL ) over 100, which is greater than that of the conventional organic CPL-dye.

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