Undecylenic Acid → 1-Undecene, 11-fluoro-

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Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use.

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