Benzofuran-fused Phosphole: Synthesis, Electronic, and Electroluminescence Properties

International audienceA synthetic route to novel benzofuran-fused phosphole derivatives 3-5 is described. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Preliminary results show that 4 can be used as an emitter in OLEDs, illustrating the potential of these new compounds for opto-electronic applications

Structural Conformers of (1,3-Dithiol-2-ylidene)ethanethioamides: The Balance Between Thioamide Rotation and Preservation of Classical Sulfur-Sulfur Hypervalent Bonds

The reaction of N-(2-phthalimidoethyl)-N-alkylisopropylamines and S2Cl2 gave 4-N-(2-phthalimidoethyl)-N-alkylamino-5-chloro-1,2-dithiol-3-thiones that quantitatively cycloadded to dimethyl or diethyl acetylenedicarboxylate to give stable thioacid chlorides, which in turn reacted with one equivalent of aniline or a thiole to give thioanilides or a dithioester. Several compounds of this series showed atropisomers that were studied by a combination of dynamic NMR, simulation of the signals, conformational analysis by DFT methods, and single crystal X-ray diffraction, showing a good correlation between the theoretical calculations, the experimental values of energies, and the preferred conformations in the solid state. The steric hindering of the crowded substitution at the central amine group was found to be the reason for the presence of permanent atropisomers in this series of compounds and the cause of a unique disposition of the thioxo group at close-to-right angles with respect to the plane defined by the 1,3-dithiole ring in the dithiafulvene derivatives, thus breaking the sulfur–sulfur hypervalent bond that is always found in this kind of compounds.Ministerio de Economıá y Competitividad, Spain (Project CTQ2012- 31611), Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo (Project BU246A12-1), and the European Commission, Seventh Framework Programme (Project SNIFFER FP7-SEC-2012-312411

Organophosphorus derivatives for electronic devices

International audienceThis review presents the main class of organophosphorus compounds (triaryl phosphines, phosphazenes, phospholes, phosphetes and diphosphacyclobutanes), which have been used in electronic devices (organic light-emitting diodes (OLEDs), organic photovoltaic cells (OPV cells), dye-sensitized solar cells (DSSCs), organic field-effect transistors (OFETs), and electrochromic cells)

NIR-absorbing Heptamethine dyes with tailor-made counterions for application in light to energy conversion

A method to exchange the counterion of cyanine dyes to Δ-TRISPHAT– and PF6– is presented. The influence of these counterions on the photophysical and electrochemical properties of the cyanine dye in solution is discussed, and tendencies in the solid packing are highlighted by X-ray crystal structures. The compounds were applied in semitransparent bilayer organic solar cells together with C60, and a power conversion efficiency of 2.2% was achieved while maintaining a high transparency level in the visible region of 66%