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9-Phenylcarbazole

CAS# 1150-62-5

9-Phenylcarbazole

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Chemical structure

9-Phenylcarbazole

3D structure

Chemical Properties of 9-Phenylcarbazole

Cas No. 1150-62-5 SDF Download SDF
PubChem ID 70851 Appearance Cryst.
Formula C18H13N M.Wt 243.30
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 9-phenylcarbazole
SMILES C1=CC=C(C=C1)N2C3=CC=CC=C3C4=CC=CC=C42
Standard InChIKey VIJYEGDOKCKUOL-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of 9-Phenylcarbazole

Description9-Phenylcarbazole-based dendrons results in the HOMO energy level of -5.36 eV for the 3rd-generation dendrimer, very close to the work function of the ITO/PEDOT electrode (-5.2 eV), which characteristic is very advantageous for the hole injection and transport materials.
TargetsPGE

Protocol of 9-Phenylcarbazole

Structure Identification
Org Biomol Chem. 2012 Dec 21;10(47):9481-90.

Starburst dendrimers consisting of triphenylamine core and 9-phenylcarbazole-based dendrons: synthesis and properties.[Pubmed: 23117896 ]

.Novel dendrimers consisting of a triphenylamine core and 1st to 3rd generations of 9-Phenylcarbazole-based dendrons were synthesized by Suzuki coupling reaction through convergent approach.
METHODS AND RESULTS:
Their structures were confirmed by two-dimensional correlated H-H COSY and C-H HSQC NMR spectra, MALDI-TOF MS and elemental analysis. The dendrimers exhibit excellent thermal stability with 5% weight loss temperatures over 540 °C. The computer modeling reveals that the dendrons in dendrimers greatly twisted with the generation, leading to the dendrimers decreased crystalline ability. Of interest is the observation that, for an identical dendrimer, the solid film displays the similar UV absorption and luminescence emission profiles to the solution sample, indicating that, after evaporation of solvent, the rigid dendrimer can well maintain its conformational morphology and the aggregation or stacking of the chromophoric groups is significantly inhibited. All the dendrimers can emit intense fluorescence with narrow full width at half maximum (FWHM) around 46-50 nm. Moreover, with the incremental generation, the quantum efficiencies remarkably increase from 64 to 95%, suggesting that the highly contorted and bulky dendrons effectively decrease energy wastage and non-radiative decay.
CONCLUSIONS:
The synergistic effect of electron-donating triphenylamine core and 9-Phenylcarbazole-based dendrons results in the HOMO energy level of -5.36 eV for the 3rd-generation dendrimer, very close to the work function of the ITO/PEDOT electrode (-5.2 eV), which characteristic is very advantageous for the hole injection and transport materials.

J Org Chem. 2000 Jan 14;65(1):116-23.

Synthesis and characterization of monodendrons based on 9-phenylcarbazole[Pubmed: 10813904]


METHODS AND RESULTS:
A series of 9-Phenylcarbazole ethynylene monodenrons have been prepared by palladium-catalyzed coupling reactions creating well-organized arrays of redox centers. The tert-butyl groups attached to the 3,6-positions of peripheral 9-Phenylcarbazole monomers provide adequate solubility to a limited degree. Trimer and 7-mer monodendrons were prepared using a monomer with 3, 3-diethyltriazene at its focal point. To facilitate purification, the synthesis of 15-mer monodendron, however, required a monomer bearing a 3-hydroxy-3-methyl-but-1-ynyl group at its focal point as a masking group for the terminal acetylene functionality. Although the solubility was limited, high generation monodendrons were found to be readily soluble in carbon disulfide, a solvent of high polarizability.
CONCLUSIONS:
Spectroscopic studies showed that there is limited through-bond conjugation over the monodendrons, but fluorescence studies suggested the presence of long-range through-space interactions in the higher members of the series.

Org Lett. 2007 Oct 25;9(22):4531-4.

Synthesis and properties of dumbbell-shaped dendrimers containing 9-phenylcarbazole dendrons.[Pubmed: 17900196]

We report the synthesis and structural characterization of two dumbbell-shaped dendrimers incorporating 9-Phenylcarbazole units as dendrons, as well as their thermal, morphological, photophysical, and electrochemical properties.

9-Phenylcarbazole Dilution Calculator

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9-Phenylcarbazole Molarity Calculator

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Preparing Stock Solutions of 9-Phenylcarbazole

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1102 mL 20.5508 mL 41.1015 mL 82.203 mL 102.7538 mL
5 mM 0.822 mL 4.1102 mL 8.2203 mL 16.4406 mL 20.5508 mL
10 mM 0.411 mL 2.0551 mL 4.1102 mL 8.2203 mL 10.2754 mL
50 mM 0.0822 mL 0.411 mL 0.822 mL 1.6441 mL 2.0551 mL
100 mM 0.0411 mL 0.2055 mL 0.411 mL 0.822 mL 1.0275 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on 9-Phenylcarbazole

Synthesis and characterization of monodendrons based on 9-phenylcarbazole[Pubmed:10813904]

J Org Chem. 2000 Jan 14;65(1):116-23.

A series of 9-Phenylcarbazole ethynylene monodenrons have been prepared by palladium-catalyzed coupling reactions creating well-organized arrays of redox centers. The tert-butyl groups attached to the 3,6-positions of peripheral 9-Phenylcarbazole monomers provide adequate solubility to a limited degree. Trimer and 7-mer monodendrons were prepared using a monomer with 3, 3-diethyltriazene at its focal point. To facilitate purification, the synthesis of 15-mer monodendron, however, required a monomer bearing a 3-hydroxy-3-methyl-but-1-ynyl group at its focal point as a masking group for the terminal acetylene functionality. Although the solubility was limited, high generation monodendrons were found to be readily soluble in carbon disulfide, a solvent of high polarizability. Spectroscopic studies showed that there is limited through-bond conjugation over the monodendrons, but fluorescence studies suggested the presence of long-range through-space interactions in the higher members of the series.

Starburst dendrimers consisting of triphenylamine core and 9-phenylcarbazole-based dendrons: synthesis and properties.[Pubmed:23117896]

Org Biomol Chem. 2012 Dec 21;10(47):9481-90.

Novel dendrimers consisting of a triphenylamine core and 1st to 3rd generations of 9-Phenylcarbazole-based dendrons were synthesized by Suzuki coupling reaction through convergent approach. Their structures were confirmed by two-dimensional correlated H-H COSY and C-H HSQC NMR spectra, MALDI-TOF MS and elemental analysis. The dendrimers exhibit excellent thermal stability with 5% weight loss temperatures over 540 degrees C. The computer modeling reveals that the dendrons in dendrimers greatly twisted with the generation, leading to the dendrimers decreased crystalline ability. Of interest is the observation that, for an identical dendrimer, the solid film displays the similar UV absorption and luminescence emission profiles to the solution sample, indicating that, after evaporation of solvent, the rigid dendrimer can well maintain its conformational morphology and the aggregation or stacking of the chromophoric groups is significantly inhibited. All the dendrimers can emit intense fluorescence with narrow full width at half maximum (FWHM) around 46-50 nm. Moreover, with the incremental generation, the quantum efficiencies remarkably increase from 64 to 95%, suggesting that the highly contorted and bulky dendrons effectively decrease energy wastage and non-radiative decay. The synergistic effect of electron-donating triphenylamine core and 9-Phenylcarbazole-based dendrons results in the HOMO energy level of -5.36 eV for the 3rd-generation dendrimer, very close to the work function of the ITO/PEDOT electrode (-5.2 eV), which characteristic is very advantageous for the hole injection and transport materials.

Synthesis and properties of dumbbell-shaped dendrimers containing 9-phenylcarbazole dendrons.[Pubmed:17900196]

Org Lett. 2007 Oct 25;9(22):4531-4.

We report the synthesis and structural characterization of two dumbbell-shaped dendrimers incorporating 9-Phenylcarbazole units as dendrons, as well as their thermal, morphological, photophysical, and electrochemical properties.

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