Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 11, Pages 5019-5027Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5005789
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Funding
- Spanish Government [CTQ2009-07469, CTQ2011-22649, CSD2007-00006]
- Generalitat de Catalunya [2009 SGR 1441, 2009 SGR 1084]
- UAB
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An efficient and environmentally friendly photoreaction between phenyl isocyanate or pentafluorophenyl isocyanate and polyfluorinated alcohols and diols is described for the first time. New highly fluorinated urethanes and diurethanes, derived from aromatic isocyanates, are produced in good yields in a photoreaction that is apparently governed by the acidic properties of the polyfluoro alcohols and diols. The wettability properties of the new polyfluorinated diurethanes have been tested, some of them showing significantly high values of hydrophobicity and oleophobicity. This new photoreaction has also been tested in the production of a model polyfluorinated polyurethane, establishing the influence of the irradiation power in the outcome of the process, and directly achieving a molecular weight distribution corresponding to a number-average DPn = 12 and a highest DPn = 20 after 4 h of irradiation (DPn: number-average degree of polymerization).
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