C. Amato, P. Calas
Dec 3, 2003
Citations
0
Influential Citations
9
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract The α,ω-diiodoperfluorooctane is added to undecyl-10-en-1-ol through AIBN initiation yielding the monoadduct in good yield (1,2-dichloroethane, 52%). This is added to N -allylphthalimide (AIBN initiation, 1,2-dichloroethane, 81%). The resulting diiodo compound is hydrodeiodinated with Bu 3 SnH (toluene, 70%) and the alcohol function is converted to thioacetate through the Mitsunobu reaction (PPh 3 , DIAD, THF, 75%). The two protecting groups, phthalimide and thioacetate, are removed with hydrazine to give the expected amino terminated semifluorinated long-chain alkanethiol (ethanol, 80%). This compound has been designed in order to form mixed fluorinated self-assembled monolayers (SAMs) with semifluorinated long-chain alkanethiol giving access to a new platform system for biosensors. Similar results are reported starting from the α,ω-diiodoperfluorohexane.