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
Novel bifluorene based conjugated systems: synthesis and properties / Grisorio, R.; Dell'Aquila, A.; Romanazzi, Giuseppe; Suranna, Gian Paolo; Mastrorilli, Pietro; Cosma, P.; Acierno, D.; Amendola, E.; Ciccarella, G.; Nobile, C. F.. - In: TETRAHEDRON. - ISSN 0040-4020. - 62:4(2006), pp. 627-634. [10.1016/j.tet.2005.10.010]
Novel bifluorene based conjugated systems: synthesis and properties
Grisorio, R.;ROMANAZZI, Giuseppe;SURANNA, Gian Paolo;MASTRORILLI, Pietro;
2006-01-01
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 groupI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
