Graphene nanoribbon precursors and monomers suitable for preparation thereof
AssigneesBASF SE, Max-Planck-Gesellschaft Zur Foerderung Der Wissenshaften E.V.
InventorsMatthias Georg Schwab, Klaus Muellen, Xinliang Feng, Lukas Doessel
Life of this patent
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Abstract
Provided are graphene nanoribbon precursors comprising repeated units of the general formula (I) in which R1, R2 are each H, halogen, —OH, —NH2, —CN, —NO2 or a hydrocarbyl radical which has 1 to 40 carbon atoms and may be linear or branched, saturated or unsaturated and mono- or poly-substituted by halogen (F, Cl, Br, I), —OH, —NH2, —CN, and/or —NO2, where one or more CH2 groups may also be replaced by —O—, —S—, —C(O)O—, —O—C(O)—, —C(O)—, —NH— or —NR—, in which R is an optionally substituted C1C40-hydrocarbyl radical, or an optionally substituted aryl, alkylaryl or alkoxyaryl radical.
Claims4
A graphene nanoribbon precursor comprising repeat units of general formula (I)
- in which
- R1, R2 are each H, halogen, —OH, —NH2, —CN, —NO2 or a hydrocarbyl radical which has 1 to 40 carbon atoms and may be linear or branched, saturated or unsaturated and mono- or polysubstituted by halogen (F, Cl, Br, I), —OH, —NH2, —CN and/or —NO2, where one or more CH2 groups may also be replaced by —O—, —S—, —C(O)O—, —O—C(O)—, —C(O)—, —NH— or —NR—, in which R is an optionally substituted C1-C40-hydrocarbyl radical, or an optionally substituted aryl, alkylaryl or alkoxyaryl radical.
A process for preparing graphene nanoribbon precursors, comprising the Yamamoto coupling reaction of monomers of the general formula (II)
- in which
- R1, R2 are each H, halogen, —OH, —NH2, —CN, —NO2 or a hydrocarbyl radical which has 1 to 40 carbon atoms and may be linear or branched, saturated or unsaturated and mono- or polysubstituted by halogen (F, Cl, Br, I), —OH, —NH2, —CN and/or —NO2, where one or more CH2 groups may also be replaced by —O—, —S—, —C(O)O—, —O—C(O)—, —C(O)—, —NH— or —NR—, in which R is an optionally substituted C1-C40-hydrocarbyl radical, or an optionally substituted aryl, alkylaryl or alkoxyaryl radical, and
- X is halogen, trifluoromethylsulfonate or diazonium.
A process for preparing monomers of the gene a formula (II), comprising the steps of
- (i) reacting 1,3-di(biphenyl-3-yl)propan-7-one 7
- with 4,4′-dihalobenzil 9
- by Knoevenagel condensation to give the tetraarylcyclopentadienone 8
- (ii) reacting the tetraarylcyclopentadienone 8 with a tolane 10
- by Diels-Alder reaction to give the monomer of the general formula (II)
- in which
- R2 are each H, halogen, —OH, —NH2, —CN, —NO2 or a hydrocarbyl radical which has 1 to 40 carbon atoms and may be linear or branched, saturated or unsaturated and mono- or polysubstituted by halogen (F, Cl, Br, I), —OH, —NH2, —CN and/or —NO2, where one or more CH2 groups may also be replaced by —O—, —S—, —C(O)O—, —O—C(O)—, —C(O)—, —NH— or —NR—, in which R is an optionally substituted C1-C40-hydrocarbyl radical, or an optionally substituted aryl, alkylaryl or alkoxyaryl radical, and
- X is halogen, trifluoromethylsulfonate or diazonium.
A monomer for preparation of graphene nanoribbon precursors by Yamamoto coupling reaction, of the general formula (II)
- in which
- R1, R2 are each H, halogen, —OH, —NH2, —CN, —NO2 or a hydrocarbyl radical which has 1 to 40 carbon atoms and may be linear or branched, saturated or unsaturated and mono- or polysubstituted by halogen (F, Cl, Br, I), —OH, —NH2, —CN and/or where one or more CH2 groups may also be replaced by —O—, —C(O)O—, —O—C(O)—, —C(O)—, —NH— or —NR—, in which R is an optionally substituted C1-C40-hydrocarbyl radical, or an optionally substituted aryl, alkylaryl or alkoxyaryl radical, and
- X is halogen, trifluoromethylsulfonate or diazonium.
Dependencies are inferred from the claim text.