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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

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Volume 84, Issue 4


Synthesis of benzobisoxazole-based D-π-A-π-D organic chromophores with variable optical and electronic properties

James S. Klimavicz / Jared F. Mike / Achala Bhuwalka / Aimeé L. Tomlinson
  • Corresponding author
  • Department of Chemistry, North Georgia College & State University, Dahlonega, GA 30597, USA
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Malika Jeffries-EL
Published Online: 2012-03-13 | DOI: https://doi.org/10.1351/PAC-CON-11-10-23

A series of symmetrical D-π-A-π-D molecules comprised of benzo[1,2-d;4,5-d']bisoxazole (BBO) and various arylenevinylenes was synthesized via a Knoevenagel condensation of 2,6-dimethyl BBO and the corresponding aryl aldehydes. The resulting compounds had energy levels that were easily modulated and broad absorptions in the visible spectrum. They also demonstrated high fluorescence quantum yields in solution. The solvatochromism of several derivatives was examined in a number of solvents, and it was found that the emission of the triphenylamine derivative varied by almost 100 nm, depending on the polarity of the solvent. Collectively, these results indicate that the optical and electronic properties of benzobisoxazoles are readily tuned through the choice of aryl co-monomer.

Keywords: organic semiconductors; photovoltaics; polymer chemistry; synthesis; UV–vis spectroscopy


International Symposium on Novel Aromatic Compounds (ISNA-14), International Symposium on Novel Aromatic Compounds, ISNA, Novel Aromatic Compounds, 14th, Eugene, USA, 2011-07-24–2011-07-29


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About the article

Published Online: 2012-03-13

Published in Print: 2012-03-13

Citation Information: Pure and Applied Chemistry, Volume 84, Issue 4, Pages 991–1004, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-11-10-23.

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