4-Methyl-9-[(4-methyl­phen­yl)sulfon­yl]thio­pyrano[3,4-b]indole-3(9H)-thione

The title compound, C19H15NO2S3, is the first example of a dithia analogue of pyrano[3,4-b]indolone. The almost planar thio­pyrano­indole­thione ring system (r.m.s. deviation for all non-H atoms = 0.030 Å) makes a dihedral angle of 80.70 (8)° with the p-tolyl ring. In the crystal, mol­ecules are connected via C—H⋯O hydrogen bonds into two chains along the b axis. These chains are connected via π–π inter­actions between symmetry-related thio­pyrano­indole­thione ring systems [centroid–centroid distance = 3.588 (1) Å]

Functionalized Alkynes in Action - From Synthesis of Natural Products to Applications in Energy Materials and OLEDs

International audienc

Functionalized Alkynes in Action - From Synthesis of Natural Products to Applications in Energy Materials and OLEDs

International audienc

Functionalized Alkynes in Action - From Synthesis of Natural Products to Applications in Energy Materials and OLEDs

International audienc

Methods and Applications of Cycloaddition Reactions in Organic Synthesis. Edited by Nagatoshi Nishiwaki

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Rhodium-Catalyzed Crossed [2+2+2] Cycloaddition with Ynamides: Key-Strategy for the Concise Total Synthesis of 3-Oxygenated Carbazole Alkaloids

International audienceTotal syntheses of a set of naturally occurring 3-oxygenated carbazole alkaloids - 6-chlorohyellazole, carazostatin, carbazomycins A and B - are described. The key-strategy underlines a highly chemo- and regioselective rhodium-catalyzed [2+2+2] cyclotrimerization between appropriately tailored yne-ynamides and 1-methoxypropyne that is stirred by the interplay of stereoelectronic and steric effects allowing the introduction of four ring substituents of the natural carbazoles within a single step and making the overall syntheses short and efficient

Straightforward synthesis of substituted indolocarbazoles for potential applications in optoelectronic devices

Le design et la synthèse de nouveaux hétéroacènes de type ladder sont d une grande importance pour le développement de matériaux innovants ayant des applications potentielles dans le domaine de l optoélectronique. Un grand intérêt est porté sur ces molécules électro- et photo-actives de par leur utilisation dans les matériels électroniques comme les diodes électroluminescentes organiques (OLEDs), les transistors organiques à effet de champ (OFETs) et les cellules photovoltaïques. Un grand intérêt est porté sur les acènes contenant des hétéroatomes, car l interaction orbitalaire des hétéroatomes joue un rôle dans la structure p-conjuguée en changeant les gaps HOMO-LUMO par rapport à la molécule de type acène correspondant. De plus, les interactions hétéroatome-hétéroatome peuvent induire un p-stacking essentiel pour obtenir une mobilité de charge élevée. Le travail effectué au laboratoire s est donc orienté sur la synthèse d hétéroacènes possédant des atomes d azote : les indolo[3,2-b]carbazoles. Cette synthèse nécessite peu d étapes, et passe par un double couplage de Suzuki et une double réaction de Cadogan. La disposition spatiale des molécules à l état solide ainsi que les propriétés physiques ont été étudiées. Le motif idéal, qui est un empilement rapproché face-face , est aussi le plus difficile à obtenir. Il faut donc jouer sur la longueur des chaines alkyles des substituants pour modifier cet empilement. Changer les substituants sur les cotés permet de jouer sur la largeur du gap HOMO-LUMO, ce qui conduit à des propriétés de fluorescence différentes. Cette synthèse est ensuite étendue à d autres composés.The design and the synthesis of new ladder type heteroacenes are of a big interest for the development of innovative materials having potential applications in the optoelectronic field. Current research focuses on electro and photo-active molecules due to their use in electronic devices such as organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs) and photovoltaic cells. Acenes containing heteroatoms have been of great interest. Indeed, the orbital interaction of the heteroatoms plays a role in the p-conjugated structure by changing the HOMO-LUMO gaps compared with the corresponding acene type molecule. Furthermore, heteroatom-heteroatom interactions can lead to an essential p -stacking to obtain high charge mobility. The laboratory work thus turned to the synthesis of heteroacenes possessing nitrogen atoms: the indolo[3,2-b]carbazoles. There syntheses require only a few steps and include a double Suzuki coupling and a double Cadogan reaction. The arrangement in the solid state was investigated together with the photophysical and electrochemical properties in solution. The best packing is the p-stacking motif that is also the most difficult to obtain. It is thus necessary to play on the length of the alkyl chains of substituents to modify the packing. The modification of the side substituents allows tuning the HOMO-LUMO gap and led to different properties of fluorescence. This synthesis was then extended to other compounds.CAEN-BU Sciences et STAPS (141182103) / SudocSudocFranceF

L-Shaped Acenes and their Excimer Emissions Obtained from Aggregates in the Solid State

International audienc

L-Shaped Acenes and their Excimer Emissions Obtained from Aggregates in the Solid State

International audienc