The 4,4'-bipyridinium-based cyclophane cyclo(paraquat-2,3,5,6-tetrafluoro-p-phenylene- paraquat) was prepared by the template-directed synthesis in a 21% yield, of which the starting material 1,4-bis(bromomethyl)-2,3,5,6-tetrafluorobenzene was prepared by the esterification of 2,3,5,6-tetrafluoro-p- phthalic acid with methanol, reduction with LiAlH₄ to give 1,4-bis(hydroxymethyl)-2,3,5,6-tetrafluorobenzene, and then bromination with toluene and 48% HBr. The free cyclophane was characterized by MS, ¹H NMR and ¹³C NMR spectra. The influence of fluorine on the cyclophane in solution was studied by dynamic ¹H NMR spectroscopy.

Key words: 1,4-bis(bromomethyl)-2,3,5,6-tetrafluorobenzene, template, cyclophane, black hole, dynamic ¹H NMR spectroscopy, 2,3,5,6-tetrafluoro-p-phthalic acid