1 Ocak 2004 Dergi makalesi Açık Erişim

Zhao, L; Perepichka, IF; Turksoy, F; Batsanov, AS; Beeby, A; Findlay, KS; Bryce, MR

MARC21 XML

<?xml version='1.0' encoding='UTF-8'?>
<record xmlns="http://www.loc.gov/MARC21/slim">
  <leader>00000nam##2200000uu#4500</leader>
  <datafield tag="245" ind1=" " ind2=" ">
    <subfield code="a">2,5-di(aryleneethynyl)pyrazine derivatives: synthesis, structural and optoelectronic properties, and light-emitting device</subfield>
  </datafield>
  <datafield tag="909" ind1="C" ind2="4">
    <subfield code="p">NEW JOURNAL OF CHEMISTRY</subfield>
    <subfield code="v">28</subfield>
    <subfield code="n">8</subfield>
    <subfield code="c">912-918</subfield>
  </datafield>
  <controlfield tag="001">94797</controlfield>
  <datafield tag="980" ind1=" " ind2=" ">
    <subfield code="a">user-tubitak-adresli-yayinlar</subfield>
  </datafield>
  <datafield tag="520" ind1=" " ind2=" ">
    <subfield code="a">A series of 2,5-di(aryleneethynyl) pyrazine derivatives has been synthesised in 23-41% yields by two-fold reaction of 2,5-dibromo-3,6-dimethylpyrazine 3 with ethynylarenes (arene=phenyl, 2-pyridyl, 4-ethylphenyl, 4-chlorophenyl, 4-biphenyl) under standard Sonogashira conditions [CuI, Pd(PPh3)(2)C(l)2, NEt3, THF]. Compound 3 has been converted into 2,5-diethynyl-3,6-dimethylpyrazine, which reacts with 2-iodothiophene to yield 2,5-bis(thien-2-ylethynyl)-3,6-dimethylpyrazine. In the X-ray crystal structure of 2,5-di(phenylethynyl)-3,6-dimethylpyrazine 4 the two phenyl rings are parallel and the pyrazine ring is inclined to their planes by 14.2degrees. Quantum chemical calculations establish that the HOMO-LUMO gap for 4 (3.56 eV) is lower than that of di(phenylethynyl) benzene 12 (3.72 eV). The nitrogen atoms of 4 serve to localise the HOMO on the central ring's carbon atoms, resulting in a quinoidal-type population, in contrast to 12. Cyclic voltammetric studies establish that 4 undergoes a reduction to the radical anion at ca. -1.9 V (vs. Ag/Ag+ in MeCN), which is almost reversible at high scan rates (500 mV s(-1)). The UV-vis absorption and photoluminescence profiles of 4 in cyclohexane are similar to those of 12; the emission for 4 (lambda(max) 379 and 395 nm) is red-shifted compared to 12. Single-layer OLEDs using MEH-PPV as the emissive polymer show significantly enhanced external quantum efficiencies (up to 0.07%) when 20% by weight of 2,5-di(biphenyl-4-ethynyl)-3,6-dimethylpyrazine 8 is added as a dopant: this is ascribed to the enhanced electron-transporting properties of the pyrazine system.</subfield>
  </datafield>
  <datafield tag="650" ind1="1" ind2="7">
    <subfield code="2">opendefinition.org</subfield>
    <subfield code="a">cc-by</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Perepichka, IF</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Turksoy, F</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Batsanov, AS</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Beeby, A</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Findlay, KS</subfield>
  </datafield>
  <datafield tag="700" ind1=" " ind2=" ">
    <subfield code="a">Bryce, MR</subfield>
  </datafield>
  <datafield tag="980" ind1=" " ind2=" ">
    <subfield code="b">article</subfield>
    <subfield code="a">publication</subfield>
  </datafield>
  <datafield tag="542" ind1=" " ind2=" ">
    <subfield code="l">open</subfield>
  </datafield>
  <datafield tag="100" ind1=" " ind2=" ">
    <subfield code="a">Zhao, L</subfield>
  </datafield>
  <datafield tag="260" ind1=" " ind2=" ">
    <subfield code="c">2004-01-01</subfield>
  </datafield>
  <controlfield tag="005">20210316130704.0</controlfield>
  <datafield tag="909" ind1="C" ind2="O">
    <subfield code="o">oai:zenodo.org:94797</subfield>
    <subfield code="p">user-tubitak-adresli-yayinlar</subfield>
  </datafield>
  <datafield tag="856" ind1="4" ind2=" ">
    <subfield code="z">md5:23af72f7c9438794b9bdb89b1c8ea2ee</subfield>
    <subfield code="s">261</subfield>
    <subfield code="u">https://aperta.ulakbim.gov.trrecord/94797/files/bib-68fc4603-0933-4256-81c1-cff412221e09.txt</subfield>
  </datafield>
  <datafield tag="540" ind1=" " ind2=" ">
    <subfield code="u">http://www.opendefinition.org/licenses/cc-by</subfield>
    <subfield code="a">Creative Commons Attribution</subfield>
  </datafield>
  <datafield tag="024" ind1=" " ind2=" ">
    <subfield code="a">10.1039/b401867m</subfield>
    <subfield code="2">doi</subfield>
  </datafield>
</record>