1 Ocak 2004 Dergi makalesi Açık Erişim

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

DataCite XML

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/94797</identifier>
  <creators>
    <creator>
      <creatorName>Zhao, L</creatorName>
      <givenName>L</givenName>
      <familyName>Zhao</familyName>
    </creator>
    <creator>
      <creatorName>Perepichka, IF</creatorName>
      <givenName>IF</givenName>
      <familyName>Perepichka</familyName>
    </creator>
    <creator>
      <creatorName>Turksoy, F</creatorName>
      <givenName>F</givenName>
      <familyName>Turksoy</familyName>
    </creator>
    <creator>
      <creatorName>Batsanov, AS</creatorName>
      <givenName>AS</givenName>
      <familyName>Batsanov</familyName>
    </creator>
    <creator>
      <creatorName>Beeby, A</creatorName>
      <givenName>A</givenName>
      <familyName>Beeby</familyName>
    </creator>
    <creator>
      <creatorName>Findlay, KS</creatorName>
      <givenName>KS</givenName>
      <familyName>Findlay</familyName>
    </creator>
    <creator>
      <creatorName>Bryce, MR</creatorName>
      <givenName>MR</givenName>
      <familyName>Bryce</familyName>
    </creator>
  </creators>
  <titles>
    <title>2,5-Di(Aryleneethynyl)Pyrazine Derivatives: Synthesis, Structural And Optoelectronic Properties, And Light-Emitting Device</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2004</publicationYear>
  <dates>
    <date dateType="Issued">2004-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/94797</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1039/b401867m</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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.</description>
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