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Novel bifluorene based conjugated systems: synthesis and properties |
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| Authors: | Roberto Grisorio Giuseppe Romanazzi Piero Mastrorilli Domenico Acierno Giuseppe Ciccarella |
| Affiliation: | a Department of Water Engineering and Chemistry (DIAC), Polytechnic of Bari, via Orabona, 4 I-70125 Bari, Italy b Department of Civil and Enviromental Engineering (DICA), Polytechnic of Bari, via Orabona, 4 I-70125 Bari, Italy c Department of Chemistry, University of Bari, via Orabona 4, I-70125 Bari, Italy d Department of Materials and Production Engineering (DIMP), University of Naples Federico II, p.le Tecchio 80, I-80125 Naples, Italy e Institute of Composite and Biomedical Materials (IMCB), Italy's National Research Council, p.le Tecchio 80, I-80125 Naples, Italy f Dipartimento di Ingegneria dell'Innovazione, University of Lecce, Via Monteroni, I-73100 Lecce, Italy |
| Abstract: | A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzuki cross-coupling between 7,7′-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9,9,9′,9′-tetraoctyl-2,2′-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by 1H, 13C NMR, FT-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7′-bis-[5′-carbodecaoxy-2,2′-bithiophen-5-yl]-9,9,9′,9′-tetraoctyl-2,2′-bifluorene (−3.07 eV) is strongly influenced by the presence of the ester functional group. |
| Keywords: | Functionalised oligofluorenes Suzuki coupling Yamamoto coupling Photoluminescence |
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