Air Products and Chemicals, Inc.

Axel Klauck-Jacobs

Kristen Elaine Minnich

Andrew Francis Nordquist

William Franklin Burgoyne, Jr

Steffen Zahn

Gauri Sankar Lal

Guari Sankar Lal

Kathryn Sue Hayes

Reiner Reinhard Taege

William Casteel

Pentafluorosulfanyl-substituted thienothiophene monomers and conducting polymers

Thienothiophene monomers having an SFgroup and conducting oligomers and polymers formed by the polymerization of such monomers and their use as hole injection materials, charge transport materials, or as semiconductors. The compound may be of the formula: where X and X' are independently H, halogen atoms (e.g., F, Cl, Br, and I), MgCl, MgBr, MgI, Sn(R&#x2032;), where R&#x2032; is Calkyl or &#x2014;OCalkyl, boronic acid, boronic ester, &#x2014;CH&#x2550;CHR&#x2033; (where R&#x2033; is H or Calkyl), &#x2014;OCalkyl, &#x2014;COOCalkyl, &#x2014;S&#x2014;COR&#x2032;&#x2033; and &#x2014;COR&#x2032;&#x2033; (where R&#x2032;&#x2033; is H or Calkyl), &#x2014;C&#x2261;CH, or polymerizable aromatic rings (such as phenyl, naphthalene, pyrrole, dithiophene, thienothiophene, thiophene and so forth.

Thienothiophene monomers having an SFgroup and conducting oligomers and polymers formed by the polymerization of such monomers and their use as hole injection materials, charge transport materials, or as semiconductors. The compound may be of the formula: where X and X' are independently H, halogen atoms (e.g., F, Cl, Br, and I), MgCl, MgBr, Mgl, Sn(R&#x2032;), where R&#x2032; comprises Calkyl or &#x2014;OCalkyl, boronic acid, boronic ester, &#x2014;CH&#x2550;CHR&#x2033; (where R&#x2033; comprises H or Calkyl), &#x2014;OCalkyl, &#x2014;COOCalkyl, &#x2014;S&#x2014;COR&#x2032;&#x2033; and &#x2014;COR&#x2032;&#x2033; (where R&#x2032;&#x2033; comprises H or Calkyl), &#x2014;C&#x2261;CH, or polymerizable aromatic rings (such as phenyl, naphthalene, pyrrole, dithiophene, thienothiophene, thiophene and so forth).

A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds using various bases and a method of preparing intermediates thereof. A method for making a vicinal difluoro halogenated aromatic compound including providing a tetrafluoro derivative of a halogen substituted aromatic compound, wherein the tetrafluoro derivative has two fluorine atoms on each of two adjacent carbons and at least one additional halogen substituent; reacting the tetrafluoro derivative with a reducing agent in presence of a base for a reaction time sufficient to form the vicinal difluoro halogenated aromatic compound containing two vicinal fluorine substituents and the at least one additional halogen substituent, wherein the reducing agent is used in a reducing agent effective amount sufficient to retain the at least one additional halogen substituent.

Synthesis of vicinal difluoro aromatics and intermediates thereof

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Whitehall, PA, United States of America

Axel Klauck-Jacobs