The present invention relates to a novel polycyclic aromatic organic semiconductor compound and a method for preparing the same, and an organic semiconductor composition, organic semiconductor thin film, and electronic, optical, or electro-optical element containing the compound. The novel organic semiconductor compound according to the present invention has high crystallinity and control capability, and facilitates control of doping conditions in the manufacture of organic semiconductor element so that it can be used for diverse applications. The compound can be mass-produced at low cost and has high solubility in organic solvents so that a liquid phase process can be applied to the manufacture of semiconductor elements and the like, thus enabling the mass-production of semiconductor elements and solar cells at low cost.

Novel organic semiconductor compound, method for preparing same, and organic semiconductor composition, and organic semiconductor thin film and element containing same

Methods for the synthesis of substituted and unsubstituted indoloindoles are considered. Characteristic features of electrophilic substitution in the indoloindole system and some transformations in the side chains are discussed.

http://iopscience.iop.org/article/10.1070/RC2007v076n04ABEH003684/pdf

The chemistry of indoloindoles

The objective of this review is to give an overview of the synthetic methods to prepare different indolo[3,2-b]carbazoles and similar systems with a potential use in electro-optical devices such as OLEDs (organic light emitting diode), OPVs (organic photovoltaic) and OFETs (organic field effect transistor). Some further modifications to the core units and their implications for specific applications are also discussed.

Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials.

A series of substituted indoles have been synthesized by the sequential reaction of aromatic aldehydes with ethyl azidoacetate in the presence of sodium ethoxide to form the corresponding ethyl α-azido-β-arylacrylates (Knoevenagel process) followed by a solvent mediated thermolysis (Hemetsberger process). The isolated yields of the ethyl α-azido-β-arylacrylates were significantly increased when employing the sacrificial electrophile ethyl trifluoroacetate. 1H NMR and coupled 1H–13C NMR analysis of the ethyl α-azido-β-arylacrylates indicate that the condensation is stereospecific—only the Z-isomer could be detected. Solvent mediated thermal treatment of the meta-substituted ethyl α-azido-β-arylacrylates resulted in the formation of both the 5- and 7- substituted indoles—the 5-regioisomer being slightly favored over the 7-regioisomer. Analogous thermal treatment of (2Z, 2Z′)-diethyl 3,3′-(1,3-phenylene)bis(2-azidoacrylate) and (2Z, 2Z′)-diethyl 3,3′-(1,4-phenylene)bis(2-azidoacrylate) exclusively produced pyrroloindoles, diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate and diethyl 1,5-dihydropyrrolo[2,3-f]indole-2,6-dicarboxylate, respectively. Results are also reported which indicate that the α-azido-β-arylacrylates can be used in the subsequent Hemetsberger indolization process without prior purification.

Indoles via Knoevenagel–Hemetsberger reaction sequence

Diversified Synthetic Strategies for Pyrroloindoles: An Overview

A method for the predominant synthesis of linear pyrroloindoles was developed, based on the attachment of the pyrrole ring to indoline and including diazo coupling of 5-and 6-aminoindolines followed by reduction, condensation with pyruvic acid ethyl ester, and indolization of the resulting 5-and 6-indolinylhydrazines. The in vitro antimicrobial, tuberculostatic, and antifungal activities of a number of 3H,6H-pyrrolo[3,2-e]indole, 1H,7H-pyrrolo[3,2-f]indole, and 1H,5H-pyrrolo[3,2-f]indole derivatives were studied. 1-(p-Chlorophenylazo)-3H,6H-pyrrolo[3,2-e]indole (XIX) and 3,5-di(p-chlorophenylazo)-1H,7H-pyrrolo[3,2-f]indole (XXIII) had high, 1-(p-nitrophenylazo)-3H,6H-pyrrolo[3,2-e]indole (XX) had moderate, and 2,7-diethoxycarbonyl3H,6H-pyrrolo[3,2-e]indole (XVIII) had weak tuberculostatic activity. 3,5-p-Chlorophenylazo)-1H,7H-pyrrolo[3,2-f]indole (XXIII) had high activity against Gram-negative bacteria.

Synthesis and antimicrobial activity of a number of pyrroloindole derivatives

Ethyl pyruvate 1-acetyl-5-indolinylhydrazone was obtained by diazotization of 1-acetyl-5-aminoindoline with subsequent reduction of the diazonium salt and condensation of the hydrazine with ethyl pyruvate. A mixture of hydrogenated derivatives of linear and angular pyrroloindoles is formed as a result of cyclization of the hydrazone in polyphosphoric acid esters. Subsequent hydrolysis, decarboxylation, and dehydrogenation lead to 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo-[3,2-e]indole.

Pyrroloindoles. 6. New synthesis of 1H, 5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole

Convenient methods have been developed for the synthesis of derivatives of angular and linear pyrroloindoles. The first such method involves the bicyclization of m-phenylenebishydrazone of ethyl pyruvate in polyphosphates through the Fischer reaction with simultaneous formation of two pyrrole rings. The second method is based on attaching a pyrrole ring to an indoline molecule.

Pyrroloindoles. 22.* optimization of preparative methods for some isomeric pyrroloindoles

Indole derivatives. Some aspects of the e. Fischer reaction

Cyclization of the m-phenylen- and 2,7-naphthylendihydrazones of acetone leads to formation of dimethyl substituted, angular pyrrolo- and indolo-indoles. Cyclization of the 2,7-naphthylendihydrazone of cyclohexanone gives the linear 1H,12H-2,3,4,5,8,9,10,11-octahydrocarbazolo[3,4-d]carbazole. A further impurity of an angular ditetrahydrocarbazolocarbazole is also formed.

D. O. Kadzhrishvili

Papers

Synthesis and antimicrobial activity of a number of pyrroloindole derivatives

Pyrroloindoles. 6. New synthesis of 1H, 5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole

Pyrroloindoles. 22.* optimization of preparative methods for some isomeric pyrroloindoles

Indole derivatives. Some aspects of the e. Fischer reaction

Pyrroloindoles. 14. Synthesis of dimethyl substituted pyrrolo[2,3-e]indole, indolo[4,5-e]indole, and some ditetrahydrocarbazolocarbazoles