Extended Tetrathiafulvalene Multi-Redox Systems Incorporating 4,5-Dihydroazuleno[2,1,8-ija]azulene Cores.

The introduction of 4,5-dihydroazuleno[2,1,8-ija]azulene as a central core between two 1,4-dithiafulvene (DTF) units provides a novel class of extended tetrathiafulvalene (TTF) electron donors. Herein we present the synthesis of such compounds with the azulenoazulene further expanded by annulation to benzene, naphthalene, or thiophene rings. Moreover, unsymmetrical donor-acceptor chromophores with one DTF and one carbonyl at the central core are presented.

Extended tetrathiafulvalene with a pentaleno[1,2-:4,5-']difluorene core - a donor-acceptor multi-redox system.

A novel extended tetrathiafulvalene was prepared by introducing the large pentaleno[1,2-:4,5-']difluorene as a central polycyclic aromatic hydrocarbon moiety. This compound behaved as a multi-redox system that could take reversibly six redox states (-1, 0, +1, +2, +3, +4). The compound exhibited strong absorptions in the visible region with an end-absorption almost reaching to 700 nm.

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units.

Large donor-acceptor scaffolds derived from polycyclic aromatic hydrocarbons (PAHs) with tunable HOMO and LUMO energies are important for several applications, such as organic photovoltaics. Here, we present a large selection of PAHs based on central indenofluorene (IF) or fluorene cores and containing various dithiafulvene (DTF) donor units that gain aromaticity upon oxidation and a variety of acceptor units, such as vinylic diesters, enediynes, and cross-conjugated radiaannulenes (RAs) that gain aromaticity upon reduction. In some cases, the DTF units are expanded by pyrrolo annelation.

Electronic Materials: An Antiaromatic Propeller Made from the Four-Fold Fusion of Tetraoxa[8]circulene and Perylene Diimides.

The synthesis of an antiaromatic tetraoxa[8]circulene annulated with four perylene diimides (PDI), giving a dynamic non-planar π-conjugated system, is described. The molecule contains 32 aromatic rings surrounding one formally antiaromatic planarized cyclooctatetraene (COT). The intense absorption (ϵ=3.

Dianthracenylazatrioxa[8]circulene: Synthesis, Characterization and Application in OLEDs.

A soluble, green-blue fluorescent, π-extended azatrioxa[8]circulene was synthesized by oxidative condensation of a 3,6-dihydroxycarbazole and 1,4-anthraquinone by using benzofuran scaffolding. This is the first circulene to incorporate anthracene within its carbon framework. Solvent-dependent fluorescence and bright green electroluminescence accompanied by excimer emission are the key optical properties of this material.