LAUSR

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 19F 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.