Electrogenerated chemiluminescence of 9,10-diphenylanthracene, rubrene, and anthracene in fluorinated aromatic solvents

The Journal of Physical Chemistry. a
David J VinyardM M Richter

Abstract

The electrogenerated chemiluminescence (ECL) of 9,10-diphenylanthracene (DPA), rubrene, and anthracene has been studied in fluorinated aromatic solvents. Mixed annihilation ECL between aromatic luminophores and quinones was observed in solvent systems containing acetonitrile and either benzene, benzotrifluoride, 3-fluorobenzotrifluoride, or 1,3-bis(trifluoromethyl)benzene. Increases in ECL efficiency (phi ecl, photons generated per redox event) correlated with decreasing solvent polarity when 1,4-benzoquinone was used as a nonemitting ECL partner. However, opposite results were observed using 1,4-naphthaoquinone (NQ) as a nonemitting partner. phi ecl also correlated with radical anion stability of NQ in these solvent systems, as indicated by reverse/forward current ratios ( I r/ I f), suggesting noncovalent interactions between the solvent and the nonemitting ECL partner. Specifically, the reaction of an aromatic luminophore with 1,4-naphthoquinone in acetonitrile/benzotrifluoride showed a 1.03-1.63-fold increases in ECL efficiency over that of acetonitrile/benzene. Slight blue shifts ( approximately 3 nm) in photoluminescence and ECL emissions were seen as solvent polarity increased. Reaction enthalpies of each system were est...Continue Reading

References

Jun 10, 2004·Chemical Reviews·Mark M Richter
Jul 3, 2007·Analytical Chemistry·David J Vinyard, Mark M Richter

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Citations

Jul 14, 2009·Chemistry : a European Journal·Jean-Hubert OlivierRaymond Ziessel
Jan 28, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Niall S PenningtonBrenden Carlson
Jan 18, 2013·The Journal of Organic Chemistry·Yutaka FujiwaraKenji Kobayashi
Sep 7, 2012·The Journal of Organic Chemistry·Palani Natarajan, Michael Schmittel
Jan 1, 2011·Analytical Methods : Advancing Methods and Applications·Guo GuangmeiXi Chen

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