@article{Januszewski2011-11-04Unsym-39249,
  year={2011},
  doi={10.1002/chem.201101701},
  title={Unsymmetrically Substituted 9,10-Dihydro-9,10-diboraanthracenes as Versatile Building Blocks for Boron-Doped π-Conjugated Systems},
  number={45},
  volume={17},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={12696--12705},
  author={Januszewski, Estera and Lorbach, Andreas and Grewal, Rekha and Bolte, Michael and Bats, Jan W. and Lerner, Hans-Wolfram and Wagner, Matthias}
}

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    <dcterms:title>Unsymmetrically Substituted 9,10-Dihydro-9,10-diboraanthracenes as Versatile Building Blocks for Boron-Doped π-Conjugated Systems</dcterms:title>
    <dc:creator>Januszewski, Estera</dc:creator>
    <dc:creator>Bats, Jan W.</dc:creator>
    <dcterms:abstract xml:lang="eng">The targeted hydrolysis of the 9,10-dihydro-9,10-diboraanthracene adduct (Me&lt;sub&gt;2&lt;/sub&gt;S)HB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BH(SMe&lt;sub&gt;2&lt;/sub&gt;) (1) with 0.5 equiv of H&lt;sub&gt;2&lt;/sub&gt;O leads to formation of the borinic acid anhydride [(Me&lt;sub&gt;2&lt;/sub&gt;S)HB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;B]&lt;sub&gt;2&lt;/sub&gt;O (2) and thereby provides access to the field of unsymmetrically substituted 9,10-dihydro-9,10-diboraanthracenes. Compound 2 reacts with tBuC≡CH to give the corresponding vinyl derivative in an essentially quantitative conversion. Subsequent cleavage of the B-O-B bridge by LiAlH&lt;sub&gt;4&lt;/sub&gt; with formation of hydridoborate functionalities is possible but is accompanied by partial B-C(vinyl) bond degradation. This situation changes when the related mesityl derivative [MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;B]&lt;sub&gt;2&lt;/sub&gt;O (7) is employed, which can be synthesized from BrB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BBr (6) by treatment with 1 equiv of MesMgBr and subsequent hydrolysis. The reaction of 7 with LiAlH&lt;sub&gt;4&lt;/sub&gt; in tetrahydrofuran (THF) furnishes Li[MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BH&lt;sub&gt;2&lt;/sub&gt;] (8); hydride elimination with Me&lt;sub&gt;3&lt;/sub&gt;SiCl leads to formation of the THF adduct MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BH(THF) (9·THF). Alternatively, 7 can be transformed into the bromoborane MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BBr (10) by treatment with BBr&lt;sub&gt;3&lt;/sub&gt;. A Br/H-exchange reaction between 10 and Et&lt;sub&gt;3&lt;/sub&gt;SiH yields the donor-free borane MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BH (9), which forms B-H-B bridged dimers (9)&lt;sub&gt;2&lt;/sub&gt; in the solid state. The vinyl borane MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;BC(H)=C(H)Mes (14) is accessible from MesC≡CH and either 9·THF or 9. Compared with the related compound Mes&lt;sub&gt;2&lt;/sub&gt;BC(H)=C(H)Mes, the electronic absorption and emission spectra of 14 reveal bathochromic shifts of Δλ(abs)=17 nm and Δλ(em)=74 nm, which can be attributed to the rigid, fully delocalized π framework of the [MesB(C&lt;sub&gt;6&lt;/sub&gt;H&lt;sub&gt;4&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt;B] chromophore.</dcterms:abstract>
    <dc:contributor>Grewal, Rekha</dc:contributor>
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    <dc:creator>Grewal, Rekha</dc:creator>
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    <dc:creator>Bolte, Michael</dc:creator>
    <dc:contributor>Bolte, Michael</dc:contributor>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2017-06-13T09:30:07Z</dc:date>
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    <dc:creator>Lerner, Hans-Wolfram</dc:creator>
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    <dc:contributor>Lerner, Hans-Wolfram</dc:contributor>
    <dc:contributor>Bats, Jan W.</dc:contributor>
    <dcterms:issued>2011-11-04</dcterms:issued>
    <dc:contributor>Januszewski, Estera</dc:contributor>
    <dc:creator>Wagner, Matthias</dc:creator>
    <dc:contributor>Lorbach, Andreas</dc:contributor>
    <dc:creator>Lorbach, Andreas</dc:creator>
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