56525-80-5

Upstream product

• 86885-08-7 9-methyl-3-(N-methylanilino)carbazole 
• 19012-03-4 N-methyl-3-formylindole 
• 6336-32-9 5H,11H-indolo[3,2-b]carbazole 
• 74-88-4 methyl iodide 
• 180331-85-5 (9-Methyl-9H-carbazol-3-yl)-phenyl-amine 
• 17754-68-6 N,N'-dimethyl-N,N'-diphenyl-1,4-phenylenediamine 
• 180331-84-4 N-(9-methyl-carbazol-3-yl)-acetamide 
• 61166-04-9 3-amino-N-methylcarbazole 

Relevant academic research and scientific papers

A General and Facile Synthesis of Heterocyclo-Fused Carbazoles

1-Methyl-2-bromo-3-indole (2), available from the regioselective bromination of 1-methyl-3-indole (1), undergoes halogen-lithium exchange with t-BuLi.The resulting carbanion 4 reacts with thiophene-3-carboxaldehyde, furan-3-carboxaldehyde, thiophene-2-carboxaldehyde, furan-2-carboxaldehyde, and indole-3-carboxaldehyde.Subsequent quenching with methyl iodide affords the corresponding methyl ether intermediates 6a-e in excellent yields.Refluxing intermediates 6a-e in 1,2,4-trichlorobenzene or 1,2-dichlorobenzene causes intramolecular cyclization followed by aromatization. 5-Methylthienocarbazole (8a), 5-methylfurocarbazole (8b), 5-methylthienocarbazole (8c), 5-methylfurocarbazole (8d), and 5,11-dimethylindolocarbazole (8e) are thus obtained in 31-67percent yields.

Molecular order of air-stable p-type organic thin-film transistors by tuning the extension of the π-conjugated core: The cases of indolo[3,2-b]carbazole and triindole semiconductors

Charge transport in organic devices depends strongly on the molecular order and morphology of the organic semiconductor thin films. In the design of new organic semiconductors, the selection of the appropriate core plays a key role in the molecular packing and charge transport characteristics of the organic device. Four derivatives of carbazole that mainly differ in the extension of the π-conjugated core, including indolo[3,2-b]carbazole and triindole derivatives, exhibited hole mobilities ranging from 10-5 to 10-2 cm2 V-1 s-1 as active layers in organic thin-film transistors (OTFTs). X-ray analyses of the single crystals and evaporated thin films gave insights into the molecular packing of the compounds that justified their OTFTs characteristics.

From ascorbigens to indolocarbazoles

New methods of L-ascorbic acid derivatization with the use of polyfunctional indole-3-cabinols are described. Reaction of β-hydroxy-N-methyltryptamine and L-ascorbic acid gave lactame derivatives; (indol-3-yl)gylcolic and L-ascorbic acids produced 2-hydroxy-4-hydroxymethyl-3-(indol-3-yl)-)-cylopen-2-enone. Similarly 4-hydroxy-3-methoxyphenylglycolic and L-ascorbic acids yielded 2-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-4-hydroxymethyl-cyclopen-2-enone. Properties of N-methoxyascorbigen (neoascorbigen) were investigated. Alkylation of L-ascorbic acid with polysubstituted pyrrolecarbinols led to pyrrole analogues of ascorbigen. Acidic transformation of 3-formylindole and 1-methyl-3-formylindole led to indolocarbazoles and triindolylmethane derivatives.

Transformations of 3-formylindoles under the action of acids

Under the influence of acids 3-formylindole forms urorosein (the salt of di(indol-3-yl)methylium) which is unstable in solution and decomposes to give a series of indole derivatives, among which 6-(indol-3-yl)-5H,7H-indolo[2,3-b]carbazole and tri(indol-3-yl)methylium salt predominate. N,N′-Dimethylurorosein in solution also forms a mixture of indole derivatives, from which tri(1-methylindol-3-yl)methylium salt, 5N,11N-dimethylindolo[3,2-b]carbazole and its 6-(1-methylindol-3-yl) derivative were isolated. 1999 KluwerAcademic/Plenum Publishers.

An expedient synthesis of 5,11-dimethylindolo[3,2-b]-carbazole, a potent ligand for the receptor for TCDD

A new and efficient synthesis has been developed for the title indolocarbazole which has been indicated by a recent computer-aided study to be a potent ligand for the receptor for the naturally occurring carcinogen, TCDD.