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.

中文翻译：

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温和条件下八氟环戊烯的多功能化

摘要 八氟环戊烯 (OFCP) 以逐步的方式与衍生自苯酚的亲核试剂发生多次取代。1 位和 5 位的乙烯基氟原子仅在第一步中发生置换，然后置换两个氟原子，2 位和 4 位各一个，除四取代外不再发生进一步置换。合成了两种带有各种侧基的半氟化线性聚合物。在第一种类型中，聚合物链是通过在 1 位和 5 位用双酚和 2 位和 4 位侧基取代而形成的。在第二种类型中，首先在 1 和 5 位引入侧基，然后在 2 和 4 位用双酚进行亲核取代。偶氮基团 (NN) 是在各种侧基中引入的功能部分之一。小有机化合物和聚合物都通过各种分析技术进行了彻底表征，包括 19F NMR 光谱、电喷雾电离飞行时间质谱分析 (ESI-TOF MS)、基质辅助激光解吸/电离飞行时间质谱（ MALDI-TOF MS)、UV-Vis 分光光度分析等。 OFCP 中发生的逐步多重取代对于制造半氟化功能有机化合物和聚合物非常有用。