Electrochemistry and Electrogenerated Chemiluminescence of n-Pentyl and Phenyl BODIPY Species: Formation of Aggregates from the Radical Ion Annihilation Reaction

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• 作者：Alexander B. Nepomnyashchii ; Martin Brring ; Johannes Ahrens ; Robin Krger ; Allen J. Bard
• 刊名：Journal of Physical Chemistry C
• 出版年：2010
• 出版时间：September 2, 2010
• 年：2010
• 卷：114
• 期：34
• 页码：14453-14460
• 全文大小：275K
• 年卷期：v.114,no.34(September 2, 2010)
• ISSN：1932-7455

文摘

The electrochemistry and the electrogenerated chemiluminescence (ECL) of the BODIPY species (2,6-diethyl-1,3,5,7-tetramethyl-8-n-pentyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, i.e., B⁸-n-pentyl), an aromatic monomer (B⁸-phenyl), and a closely related dimer were examined. The B⁸-n-pentyl species with the n-pentyl donor chain in the meso position shows good electrochemical behavior in MeCN with the formation of stable radical ions. The ECL emission is characterized by long-wavelength emission during consecutive oxidation and reduction steps. This is attributed to aggregate formation on radical ion annihilation, the extent of which increased with increasing concentration of the compound. The B⁸-phenyl electrochemistry also shows stable radical ions. However, B⁸-phenyl with the meso phenyl group ECL emission does not show any long-wavelength emission. The synthesized dimer closely related to this species shows two electrochemical oxidations with peak separations of 0.5 V and two reductions with peak separations 0.2 V, which corresponds to a high degree of intermolecular interactions in the molecule. The growth of additional electrochemical peaks during the oxidation and reduction of B⁸-n-pentyl was not seen, and both radical ions were stable, suggesting that emitting secondary products were not formed.