Synthesis of amino terminated semifluorinated long-chain alkanethiols

被引：8

作者：

Amato, C ^{[1
]}

Calas, P ^{[1
]}

机构：

[1] Univ Montpellier 2, Lab Org Mol Evolut & Mat Fluores, UMR 5073, F-34095 Montpellier 05, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 124卷 / 02期

关键词：

alpha; omega-diiodoperfluoroalkane; monoadduct; amino-terminated semifluorinated long-chain alkanethiols; mixed SAMs; biosensors;

D O I：

10.1016/j.jfluchem.2003.08.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The alpha,omega-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 Bu3SnH (toluene, 70%) and the alcohol function is converted to thioacetate through the Mitsunobu reaction (PPh3, 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 alpha,omega-diiodoperfluorohexane. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：169 / 175

页数：7

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