Luminescence Properties of New Fused Benzothiophene Derivatives and Their Conductive Oligomers Structural and Solvent Effects |
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Authors: | Jean-Jacques Aaron Zouhair Mechbal Alain Adenier Cyril Parkanyi Vaclav Kozmik Jiri Svoboda |
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Institution: | (1) ITODYS (Interfaces, Traitements, Organisation et Dynamique des Systèmes) de l'Université Paris, 7-Denis Diderot, associé au CNRS, 1, rue Guy de la Brosse, 75005 Paris, France;(2) Department of Chemistry and Biochemistry, Florida Atlantic University, Boca Raton, FL 33431-0991, USA;(3) Department of Organic Chemistry, Prague Institute of Chemical Technology, Technicka 5, 16628 Prague 6, Czech Republic |
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Abstract: | The structural and solvent effects on the electronic absorption and fluorescence spectra, and fluorescence quantum yields, of four new fused benzothiophene derivatives, including benzothieno3,2b]-thiophene (BTT), benzothieno3,2-b]benzothiophene (BTBT), 6-methoxy1]benzothieno3,2b]-thiophene (MeOBTT), and benzothieno3,2-b]indole (BTI) were investigated at 295 K. The luminescence properties of the corresponding conductive oligomers, poly(BTT) and poly (MeOBTT), electrosynthesized in acetonitrile, were also studied. Satisfactory McRae, Suppan, and Kawski-Chamma-Viallet solvatochromic correlations were established for the four monomers in most solvents. A weak negative solvatochromic behavior was found for these compounds, indicating that their dipole moments are slightly lower in the excited singlet state than in the ground state. Kamlet-Abboud-Taft multiparametric correlations were also obtained for absorption and fluorescence wave numbers and quantum yields, demonstrating the existence of specific solute-solvent interactions. In the case of the oligomers, important red-shifts of the fluorescence emission maxima (![Delta](/content/gv1q2flwbmrr0bhj/xxlarge916.gif) 90–110 nm) relative to the corresponding monomers were observed, which shows the extent of conjugated segments in the oligomer chains. |
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Keywords: | Fused benzothiophenes conductive oligomers luminescence solvent effects |
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