4.4 Article

Formation of Perfluoroalkyl Fullerene Alkylphosphonic Acid Self-Assembled Monolayers on Aluminum Oxide

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ELECTROCHEMICAL SOC INC
DOI: 10.1149/2.0281706jss

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Funding

  1. DAAD
  2. National Science Foundation [NSF/CHE-1362302, CHE-1012468]
  3. DFG Collaborative Research Center Synthetic Carbon Allotropes [SFB 953]
  4. Direct For Mathematical & Physical Scien
  5. Division Of Chemistry [1362302] Funding Source: National Science Foundation

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The possibility of fabricating self-assembled monolayers (SAMs) from alkylphosphonic acids functionalized with trifluoromethyl derivatives of C-60 on a metal oxide surface has been demonstrated in this work. Using several trifluoromethylfullerenes (TMFs) of different compositions and isomeric structures, we explored their relative reactivities in the Bingel-Hirsch cycloaddition reactions with 11-(diethoxyphosphoryl)undecyl methyl malonate for the first time. Only two isomers of C-60(CF3)(10) showed fairly selective monoadduct formation, whereas compounds with lower CF3 content showed no selectivity. Converting the phosphoric ester into a phosphoric acid moiety enabled the successful formation of self-assembled monolayers of the TMF-alkylphosphonic acid on aluminum oxide surfaces. Comparison with analogous SAMs made with underivatized C-60 showed that TMFs form more hydrophobic surfaces. (C) The Author(s) 2017. Published by ECS.

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