Cyclization of an Achiral Flipping Panel to Homochiral Tubes Exhibiting Circularly Polarized Luminescence

Macrocyclization of the bendable 2,7-dimethoxythianthrene with methylene linkages afforded a pair of homochiral macrocycles featuring a hex-nut-like geometry. Their structures were fully characterized by NMR spectroscopy, mass spectrometry, and single-crystal X-ray diffraction analysis. Their stable planar chirality facilitates efficient resolution of the pair of enantiomers which could be readily derivatized. Installing phenylethynyl groups on their rims leads to luminescent tubular macrocycles exhibiting circularly polarized luminescence with a large dissymmetry value |g_lum | of 5×10^-3 . Supramolecular binding of electron-deficient guests by the tube results in fluorescence quenching, which proved its potential for the future development of switchable chiroptical systems.