58 research outputs found
4-Methyl-9-[(4-methylÂphenÂyl)sulfonÂyl]thioÂpyrano[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 thioÂpyranoÂindoleÂthione ring system (r.m.s. deviation for all non-H atoms = 0.030â
Ă
) makes a dihedral angle of 80.70â
(8)° with the p-tolyl ring. In the crystal, molÂecules are connected via CâHâŻO hydrogen bonds into two chains along the b axis. These chains are connected via ÏâÏ interÂactions between symmetry-related thioÂpyranoÂindoleÂthione ring systems [centroidâcentroid distance = 3.588â
(1)â
Ă
]
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
International audienc
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 synthĂšse de nouveaux hĂ©tĂ©roacĂšnes de type ladder sont d une grande importance pour le dĂ©veloppement de matĂ©riaux innovants ayant des applications potentielles dans le domaine de l optoĂ©lectronique. Un grand intĂ©rĂȘt est portĂ© sur ces molĂ©cules Ă©lectro- et photo-actives de par leur utilisation dans les matĂ©riels Ă©lectroniques comme les diodes Ă©lectroluminescentes organiques (OLEDs), les transistors organiques Ă effet de champ (OFETs) et les cellules photovoltaĂŻques. Un grand intĂ©rĂȘt est portĂ© sur les acĂšnes contenant des hĂ©tĂ©roatomes, car l interaction orbitalaire des hĂ©tĂ©roatomes joue un rĂŽle dans la structure p-conjuguĂ©e en changeant les gaps HOMO-LUMO par rapport Ă la molĂ©cule de type acĂšne correspondant. De plus, les interactions hĂ©tĂ©roatome-hĂ©tĂ©roatome peuvent induire un p-stacking essentiel pour obtenir une mobilitĂ© de charge Ă©levĂ©e. Le travail effectuĂ© au laboratoire s est donc orientĂ© sur la synthĂšse d hĂ©tĂ©roacĂšnes possĂ©dant des atomes d azote : les indolo[3,2-b]carbazoles. Cette synthĂšse nĂ©cessite peu d Ă©tapes, et passe par un double couplage de Suzuki et une double rĂ©action de Cadogan. La disposition spatiale des molĂ©cules Ă l Ă©tat solide ainsi que les propriĂ©tĂ©s physiques ont Ă©tĂ© Ă©tudiĂ©es. Le motif idĂ©al, qui est un empilement rapprochĂ© face-face , est aussi le plus difficile Ă obtenir. Il faut donc jouer sur la longueur des chaines alkyles des substituants pour modifier cet empilement. Changer les substituants sur les cotĂ©s permet de jouer sur la largeur du gap HOMO-LUMO, ce qui conduit Ă des propriĂ©tĂ©s de fluorescence diffĂ©rentes. Cette synthĂšse est ensuite Ă©tendue Ă d autres composĂ©s.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
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