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

2022; Wiley; Volume: 28; Issue: 59 Linguagem: Inglês

10.1002/chem.202202218

1521-3765

Masashi Hasegawa, Chika Hasegawa, Yuki Nagaya, Kazunori Tsubaki, Yasuhiro Mazaki,

Axial and Atropisomeric Chirality Synthesis

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 - dimers, trimers, and tetramers - adopt figure-of-eight, Möbius triangle, and concave rectangle structures, respectively. These homologues have large ϵ values in their UV-vis absorption spectra because of the π-conjugation of the naphthalene-phenylene-naphthalene frameworks. Owing to the shape-persistent ring structure and tethering with -OCH2 CH2 O-, high fluorescence quantum yields and a relatively high dissymmetry factor gCPL in circularly polarized luminescence (CPL) spectra were achieved. This results in CPL brightness (BCPL ) of over 100, which is greater than that of the conventional organic CPL dye.