Product Name	(4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic acid
CAS Number	1240963-55-6
Molecular Formula	C₂₄H₁₈BNO₂
Molecular Weight	363.22
SMILES Code	OB(C1=CC=C(C2=CC3=C(C=C2)N(C4=CC=CC=C4)C5=C3C=CC=C5)C=C1)O
MDL Number	MFCD30063200
Pubchem ID	58351149
InChI Key	CFZRUXMJHALVPF-UHFFFAOYSA-N

Synthetic Route

Synthesis：1240963-55-6

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121-43-7		1028647-93-9		1240963-55-6

Productivity	Synthesis	Experimental procedure
88%	Stage #1: at -78 - 20℃; for 20 h; Inert atmosphere Stage #2: With hydrogenchloride In tetrahydrofuran; water for 7 h;	Example 2: In this example, an example of preparing 3-[4-(9-phenanthrenyl)-phenyl]-9-phenyl-9H-carbazole (abbreviation: PCPPn) represented by structural formula (102) in embodiment 1 is described. Step 1: Synthesis method of 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid To a 300 mL three-necked flask was added 8.0 g (20 mmol) of 3-(4-bromophenyl)-9-phenyl-9H-carbazole obtained in reaction scheme (F1-2), the atmosphere in the flask was replaced with nitrogen, and then 100 mL of dehydrated tetrahydrofuran (abbreviation: THF) was added to the flask, and the temperature was lowered to -3.4 mL (30 mmol) of trimethyl borate was added to the mixture, and the mixture to which trimethyl borate was added was stirred at -78°C for 2 hours and at room temperature for 18 hours. After the reaction, 1M dilute hydrochloric acid was added to the reaction solution until the solution became acidic. The solution was stirred for 7 hours. The solution was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine. After washing, magnesium sulfate was added to the organic layer to remove moisture. The suspension was filtered, the resulting filtrate was concentrated, and hexane was added. The mixture was irradiated with ultrasound and then recrystallized to obtain 6.4 g of a white powder, the target substance, with a yield of 88%. The reaction scheme for step 1 (F2-1) is shown.
88%	Stage #1: With n-butyllithium In tetrahydrofuran; Hexane at -78℃; for 2 h; Inert atmosphere Stage #2: at -78 - 20℃; for 20 h; Stage #3: With hydrogenchloride In tetrahydrofuran; Hexane; water for 7 h; Inert atmosphere	Step 1: Synthesis of 4-(9-phenyl-9H-carbazol-3-yl)phenylboronic acid: In a 300 mL three-necked flask, 8.0 g (20 mmol) of 3-(4-bromophenyl)-9-phenyl-9H-carbazole was placed. The air in the flask was replaced with nitrogen, 100 mL of dehydrated tetrahydrofuran (THF) was added, and the temperature was lowered to -78°C. To this mixed solution, 15 mL (24 mmol) of a 1.65 mol/L n-butyllithium hexane solution was added dropwise. The mixed solution with the n-butyllithium hexane solution was stirred for 2 hours. To this mixture was added 3.4 mL (30 mmol) of trimethyl borate, and the mixture was stirred at -78°C for 2 hours and at room temperature for 18 hours. After the reaction, 1 M dilute hydrochloric acid was added to the reaction solution until the solution became acidic. The solution with the added dilute hydrochloric acid was stirred for 7 hours. The solution was extracted with ethyl acetate, and the resulting organic layer was washed with a saturated aqueous sodium chloride solution. After washing, magnesium sulfate was added to the organic layer to absorb moisture. The suspension was filtered, the resulting filtrate was concentrated, and hexane was added thereto. The mixture was irradiated with ultrasound and then recrystallized to obtain 6.4 g of a white powder, which was the target of synthesis, with a yield of 88%. The reaction scheme of the above step 1 is described below. [0361] The Rf values of the target substance and 3-(4-bromophenyl)-9-phenyl-9H-carbazole were 0 (source) and 0.53, respectively, as determined by silica gel thin layer chromatography (TLC) (developing solvent: ethyl acetate/hexane, ratio 1:10). In addition, the Rf values of the target substance and 3-(4-bromophenyl)-9-phenyl-9H-carbazole were 0.72 and 0.93, respectively, as determined by silica gel thin layer chromatography (TLC) using ethyl acetate as the developing solvent.

Chemical Properties

This extended polycyclic aromatic compound forms a white to off-white crystalline powder with a high melting point of 182-186°C and a very high predicted boiling point of 555.9°C,reflecting its large,rigid,and planar structure.The density is estimated at 1.18 g/cm³.Solubility is poor in non-polar solvents like hexane but good in polar aromatic solvents such as THF,1,4-dioxane,and DMF.For stability,it must be stored under an inert atmosphere(nitrogen/argon)at 2-8°C in a sealed,moisture-proof container.The boronic acid group benefits from the molecule's extended conjugation,which can stabilize the boronic acid form.

Description

[4-(9-Phenylcarbazol-3-yl)phenyl]boronic acid is a state-of-the-art building block designed for advanced organic optoelectronics.It elegantly conjugates a carbazole unit-a classic,hole-transporting,and highly luminescent motif with excellent thermal and morphological stability-with a pendant phenylboronic acid via a single bond.The 9-position of the carbazole is substituted with a phenyl ring,which disrupts excessive crystallization and promotes the formation of stable amorphous glasses-a critical property for thin-film device fabrication.This molecular design seamlessly integrates excellent charge-transport capability with the versatile synthetic handle of the boronic acid,enabling its incorporation into larger,precisely defined conjugated systems via cross-coupling reactions.

Uses

1.Pharmaceutical Synthesis

While not a typical drug intermediate,its large,planar,and fluorescent structure makes it a candidate for developing therapeutic agents that function via intercalation(e.g.,as DNA binders in oncology)or as imaging agents.The boronic acid allows conjugation to targeting vectors.

2.Agrochemical R&D

Potential use is limited but could be explored in the design of fluorescent tracers or probes to study the uptake,translocation,and metabolism of agrochemicals within plants,leveraging its strong fluorescence.

3.Functional Material Synthesis

This is its primary and most significant application.It is a core monomer for high-performance OLED and OPV materials.

● OLEDs:Used in Suzuki polycondensation to synthesize host materials,emitters(especially for blue light),and electron-blocking layers.The carbazole ensures good hole transport,while the boronic acid enables precise extension of conjugation to tune the emission color and energy levels.

● OPVs:Serves as a building block for donor polymers or small-molecule donors in organic solar cells.

● Other:Used in perovskite solar cells as a hole-transporting material component and in the synthesis of covalent organic frameworks(COFs)for photocatalysis or sensing.

4.Organic Synthesis Building Block

A premium reagent for constructing complex polycyclic aromatic hydrocarbons(PAHs)and nanographenes with nitrogen heteroatoms.It is essential for materials scientists developing next-generation organic semiconductors,where the carbazole's electronic properties and the boronic acid's coupling reliability are paramount.

(4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic Acid

Synthetic Route

Chemical Properties

Description

Uses