A multifunctionalization of octafluorocyclopentene under mild conditions

Abstract Octafluorocyclopentene (OFCP) undergoes multiple substitutions with nucleophiles derived from phenols in a stepwise manner. The vinylic fluorine atoms at 1 and 5-positions undergoes displacement exclusively in the first step followed by the displacement of two fluorine atoms, one each at 2 and 4-positions and no further substitution occurs beyond the tetrasubstitution. Two types of semi-fluorinated linear polymers bearing various pendant groups were synthesized. In the first type, the polymer chain was formed by substitution at 1 and 5-positions with bisphenols and pendant groups at 2 and 4-positions. In the second type, the pendant groups were introduced at 1 and 5-positions first followed by the nucleophilic substitutions at 2 and 4-positions with bisphenols. Azo group ( N N ) was one of the functional moieties introduced among the various pendant groups. Both small organic compounds as well as polymers were thoroughly characterized by various analytical techniques including 19 F NMR spectroscopy, electrospray ionization time-of-flight mass analysis (ESI-TOF MS), matrix assisted laser desorption/ionization time-of-flight mass spectroscopy (MALDI-TOF MS), UV–Vis spectrophotometric analysis, etc. The stepwise, multiple substitution occurring in OFCP is highly useful for making semi-fluorinated functional organic compounds and polymers.