title: Conjugated Thiophene-Fused Isatin Dyes through Intramolecular Direct Arylation.
abstract: We report on the design, synthesis, and properties of innovative, planar, π-conjugated compounds in which a thiophene ring is fused with the skeleton of the naturally occurring dye isatin. The synthesis is achieved in high yields making use of an intramolecular direct arylation reaction as the key step, making the overall process potentially scalable. The synthetic sequence has been demonstrated also for an isatin bearing fluorine substituents on the aromatic ring. NMR and X-ray studies demonstrate the crosstalk occurring between the fused, coplanar, and conjugated moieties, making these novel dyes with a donor-acceptor character. Cyclic voltammetry and UV-vis studies confirm very interesting HOMO-LUMO levels and energy gaps for the new compounds.
authors.affiliation: Department of Chemistry, University of Pavia , Viale Taramelli, 12, 27100 Pavia, Italy.
authors.forename: Andrea
authors.initials: A
authors.lastname: Nitti
authors.affiliation: Department of Chemistry, University of Pavia , Viale Taramelli, 12, 27100 Pavia, Italy.
authors.forename: Marco
authors.initials: M
authors.lastname: Signorile
authors.affiliation: Centro Grandi Strumenti, University of Pavia , Via Bassi 21, 27100 Pavia, Italy.
authors.forename: Massimo
authors.initials: M
authors.lastname: Boiocchi
authors.affiliation: Research Center for Renewable Energies and Environment, Istituto Donegani, Eni Spa , Via Fauser 4, 28100 Novara, Italy.
authors.forename: Gabriele
authors.initials: G
authors.lastname: Bianchi
authors.affiliation: Research Center for Renewable Energies and Environment, Istituto Donegani, Eni Spa , Via Fauser 4, 28100 Novara, Italy.
authors.forename: Riccardo
authors.initials: R
authors.lastname: Po
authors.affiliation: Department of Chemistry, University of Pavia , Viale Taramelli, 12, 27100 Pavia, Italy.|INSTM Research Unit, University of Pavia , Viale Taramelli, 12, 27100 Pavia, Italy.
authors.forename: Dario
authors.initials: D
authors.lastname: Pasini