57103-02-3

Basic information

• Product Name: 9H-Carbazole, 3,6-diiodo-
• Synonyms: 3,6-Diiodocarbazole;6-diiodo-9H-carbazole;9H-Carbazole, 3,6-diiodo-;3,6-Diiodo-9H-carbazole
• CAS NO: 57103-02-3
• Molecular Formula: C₁₂H₇I₂N
• Molecular Weight: 418.99962
• Mol File: 57103-02-3.mol

Chemical Properties

• Melting Point: 205.0 to 209.0 °C
• Boiling Point: 498.3±25.0 °C(Predicted)
• Appearance: /
• Density: 2.326±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 15.68±0.30(Predicted)
• CAS DataBase Reference: 9H-Carbazole, 3,6-diiodo-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Carbazole, 3,6-diiodo-(57103-02-3)
• EPA Substance Registry System: 9H-Carbazole, 3,6-diiodo-(57103-02-3)

Safety Data

• Hazardous Substances Data: 57103-02-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
9H-Carbazole, 3,6-diiodois used as a precursor for the synthesis of various organic compounds, contributing to the development of new pharmaceuticals due to its unique chemical structure and properties.
Used in Industrial Applications:
In the industrial sector, 9H-Carbazole, 3,6-diiodoserves as a building block for the development of new materials, leveraging its chemical composition to create innovative products with enhanced characteristics.
Used in Organic Electronic Devices:
9H-Carbazole, 3,6-diiodois utilized in the design and fabrication of organic electronic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells, where its chemical properties are crucial for device performance and efficiency.
Used in Antimicrobial Agents Development:
Due to its antimicrobial properties, 3,6-Diiodocarbazole is being explored for the development of new antimicrobial agents, offering potential solutions to combat resistant strains of bacteria and other pathogens.

Upstream product

• 86-74-8 9H-carbazole 
• 64-19-7 acetic acid 
• 1592-95-6 3-bromo-9H-carbazole 
• 100-44-7 benzyl chloride 

Downstream Products

• 606129-89-9 9-acetyl-3,6-diiodo carbazole 
• 78932-83-9 3,6-di((E)-styryl)-9H-carbazole 
• 62913-24-0 3,6-bis(2-phenylethynyl)-9H-carbazole 
• 56525-79-2 3,6-diphenylcarbazole 
• 943786-98-9 C₃₂H₃₁N₃O₄ 
• 943787-00-6 C₃₆H₃₉N₃O₄ 
• 943787-02-8 C₃₆H₃₉N₃O₄ 
• 501330-43-4 1,8-diiodo-3,6-diphenyl-carbazole 
• 399042-83-2 3,6-bis(4-methoxyphenyl)-9H-carbazole 
• 1246891-46-2 3,6-di(2,6-dimethylphenyl)-9H-carbazole 
• 313268-34-7 1-(3,6-diiodo-9H-carbazol-9-yl)-3-(phenylamino)propan-2-ol 
• 1238156-30-3 3,6-bis(4-hexylphenyl)-9H-carbazole 
• 1253184-56-3 ethyl 2-(3,6-bis(4-hexylphenyl)-9H-carbazol-9-yl)acetate 
• 1258207-82-7 1-(3,6-bis(4-hexylphenyl)-9H-carbazol-9-yl)-4-hydroxy-5,5-dimethylhex-3-en-2-one 

Relevant articles and documents

(Bi)phenyl substituted 9-(2,2-diphenylvinyl)carbazoles as low cost hole transporting materials for efficient red PhOLEDs

Two low-cost 9-(2,2-diphenylvinyl)carbazole-based derivatives with aryl substitutions were synthesized by simple procedure and then investigated. The respective glass transition temperatures of the materials were estimated to be higher than 90 °C, which can provide morphologically-stable amorphous films for applications in organic light emitting diodes. The compounds possess adequate ionization potentials and suitable triplet energies, which make them suitable hole transporting materials for use in red phosphorescent organic light-emitting diodes. The respective peak efficiencies of the red devices with the p-type dopants were recorded at 8.7% (5.6 cd/A and 3.9 lm/W) and at 8.7% (5.4 cd/A and 3.8 lm/W), correspondingly, demonstrating high potential of the material for applications in light emitting diodes. The characteristics indicated that the devices with the aryl substituted 9-(2,2-diphenylvinyl)carbazoles exhibit better performance than those of widely used hole transporting 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC) -based device.

Easy accessible blue luminescent carbazole-based materials for organic light-emitting diodes

The thermal, optical, electrochemical and charge transport properties of a series of nine straightforward carbazole-based compounds have been analysed and interpreted according to their molecular structure by means of the X-ray analysis of single crystals. A non-doped OLED device with low turn-on voltage and maximum luminance up to 1.4 × 104 cd m?2 was achieved. DFT calculations have been performed to explain the high efficiency of radiative exciton production.

Solution-processable naphthalene and phenyl substituted carbazole core based hole transporting materials for efficient organic light-emitting diodes

Solution-processable molecular hole transporting materials (HTMs) are extremely crucial in order to realize low cost, high throughput, and roll-to-roll fabrication of large area organic light emitting diodes for display and lighting applications. In this report, a series of naphthalene and phenyl substituted carbazole core based HTMs, 3-(1-naphthyl)-9-(2-phenylvinyl)carbazole (NPVCz), 3,6-di-(1-naphthyl)-9-phenylvinylcarbazole (DNPVCz), and 3,6-diphenyl-9-(2-phenylvinyl)carbazole (DPPVCz) are successfully synthesized and characterized. The synthesized HTMs possess excellent solubility in common organic solvents. By using a fluorescent tris(8-hydroxyquinolinato)aluminium emitter, we demonstrate an enhancement of 135%, from 1.7 to 4.5 cd A-1, in the current efficiency of an organic light emitting diode (OLED) by replacing the conventional HTM, N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (NPB), with the NPVCz counterpart. Moreover, the current efficiency of a conventional tris[2-phenylpyridinato-C2,N]iridium(iii) based phosphorescent green OLED device increases from 46.4 to 66.2 cd A-1 by substituting the NPB with NPVCz. These findings suggest that this type of solution-processable molecular HTM will be a promising contender for high efficiency OLED devices.

A one-pot direct iodination of the Fischer-Borsche ring using molecular iodine and its utility in the synthesis of 6-oxygenated carbazole alkaloids

An efficient regioselective iodination of the Fischer-Borsche ring has been achieved using molecular iodine, in a one-pot synthesis. The acid-, metal-, and oxidant-free conditions of the present method are highly convenient and practical. Furthermore, the one-pot direct iodination process is extended to the concise synthesis of glycozoline, 3-formyl-6-methoxy-carbazole, and 6-methoxy-carbazole-3-methylcarboxylate natural alkaloids. This method has been proven to be tolerant to a broad range of functional groups, with good to excellent yields.

COMPOUND FOR ORGANIC ELECTROLUMINESCENT DEVICE AND ORGANIC ELECTROLUMINESCENT DEVICE HAVING THE SAME

The present invention provides a compound of formula (I) for an organic electroluminescent device: wherein X and Y are each independently selected for the group consisting of an alkyl substituted, aryl substituted or unsubstituted carbazole, indolocarbazole, triphenylsilyl and diphenylphosphine oxide represented by formula (A), (B), (C), (D) or (E), in which R1, R2, and R3 are each independently selected from the group consisting of a hydrogen, an alkyl having 1 to 15 carbons atoms, an aryl group having 6 to 15 carbons atoms, an alkyl substituted, an aryl substituted or unsubstituted triphenylsilyl, and a diphenylphosphine oxide represented by the formula (D) or (E); m and n are each independently 0 or 1, provided that m+n is 1 or more; and Ar1 and Ar2 are each independently selected from the group consisting of an alkyl substituted, aryl substituted or unsubstituted phenyl, tolyl, naphthyl, fluorenyl, anthracenyl, and phenanthryl.

SEQUENCE-SPECIFIC NUCLEIC ACID PURIFICATION METHOD MANNER

Disclosed is a method for the purification and collection of a nucleic acid comprising a specific nucleotide sequence, which can be carried out within an extremely short period and can achieve both high sequence-specificity and a high collection rate. Specifically disclosed is a method for the purification of a target nucleic acid comprising a specific nucleotide sequence and contained in a nucleic acid mixture. The method comprises the steps of: hybridizing a photo-ligating nucleic acid having a group represented by formula (I) as abase moiety with the target nucleic acid to form a hybrid; irradiating the hybrid of the photo-ligating nucleic acid and the target nucleic acid with light to cause the photo-ligation of the hybrid; removing any un-photo-ligated nucleic acid by washing; and irradiating the hybrid of the photo-ligating nucleic acid and the target nucleic acid with light to cause the photo-cleavage of the hybrid.

Enantioselective recognition of mandelic acid by a 3,6-dithiophen-2-yl-9 h -carbazole-based chiral fluorescent bisboronic acid sensor

We have prepared chiral fluorescent bisboronic acid sensors with 3,6-dithiophen-2-yl-9H-carbazole as the fluorophore. The thiophene moiety was used to extend the ?-conjugation framework of the fluorophore in order to red-shift the fluorescence emission and, at the same time, to enhance the novel process where the fluorophore serves as the electron donor of the photoinduced electron transfer process (d-PET) of the boronic acid sensors; i.e., the background fluorescence of the sensor 1 at acidic pH is weaker compared to that at neutral or basic pH, in stark contrast to the typical a-PET boronic acid sensors (where the fluorophore serves as the electron acceptor of the photoinduced electron transfer process). The benefit of the d-PET boronic acid sensors is that the recognition of the hydroxylic acids can be achieved at acidic pH. We found that the thiophene moiety is an efficient ?-conjugation linker and electron donor; as a result, the d-PET contrast ratio of the sensors upon variation of the pH is improved 10-fold when compared to the previously reported d-PET sensors without the thiophene moiety. Enantioselective recognition of tartaric acid was achieved at acid pH, and the enantioselectivity (total response KdIFd/KlI Fl) is 3.3. The fluorescence enhancement (I FSample/IFBlank) of sensor 1 upon binding with tartaric acid is 3.5-fold at pH 3.0. With the fluorescent bisboronic acid sensor 1, enantioselective recognition of mandelic acid was achieved for the first time. To the best of our knowledge, this is the first time that the mandelic acid has been enantioselectively recognized using a chiral fluorescent boronic acid sensor. Chiral monoboronic acid sensor 2 and bisboronic acid sensor 3 without the thiophene moiety failed to enantioselectively recognize mandelic acid. Our findings with the thiophene-incorporated boronic acid sensors will be important for the design of d-PET fluorescent sensors for the enantioselective recognition of α-hydroxylic acids such as mandelic acid, given that it is currently a challenge to recognize these analytes with boronic acid fluorescent molecular sensors.

LIGHT-RESPONSIVE ARTIFICIAL NUCLEOTIDE HAVING PHOTO-CROSSLINKING ABILITY

The present invention provides a photoreactive crosslinking agent that is capable of crosslinking a sequence which cannot be photo-crosslinked by psoralen, and is capable of photo-crosslinking using a light having a longer wavelength, as compared with psoralen. The present invention also provides a compound having a group represented by formula (I) coupled with a group represented by formula (II).

A useful procedure for diiodination of carbazoles and subsequent efficient transformation to novel 3,6-bis(triethoxysilyl)carbazoles giving mesoporous materials

Bis(pyridine)iodonium tetrafluoroborate (IPy2BF4) was successfully used as a diiodination reagent for carbazole and its derivatives to give 3,6-diiodocarbazoles in excellent yield. Subsequent rhodium-catalyzed disilylation of 3,6-diiodocarbazoles with triethoxysilane gave the corresponding 3,6-bis(triethoxysilyl)carbazoles, which are precursors for sol-gel polymerization, in good yield.

Generation of electrophilic iodine from iodine monochloride in neutral media. Iodination and protodeiodination of carbazole

In reaction of iodine monochloride with CF3COOAg, CH 3COONa or (CH3COO)2Pb in acetonitrile and acetic acid the chloride is bonded by metal cations, and electrophilic iodine is generated able to easily iodinate a