628336-95-8

Usage

Uses

Used in Organic Electronic Devices:
9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE is used as a key component in organic light-emitting diodes (OLEDs) for its ability to enhance device performance and stability. Its electron-transporting properties contribute to the efficient operation and longevity of OLEDs.
Used in Organic Photovoltaic Cells:
In the field of organic photovoltaic cells (OPVs), 9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE serves as an essential material that improves the efficiency and stability of solar cells. Its electron-transporting capabilities play a crucial role in the conversion of light into electricity.
Used in Organic Semiconductors:
9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE is utilized as a constituent of organic semiconductors, where its thermal stability and electron-transporting properties are harnessed to create materials with improved performance characteristics for various electronic applications.
Used in Optoelectronic Materials:
9-HEXYL-3,6-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9H-CARBAZOLE is also studied for its potential in optoelectronic materials, where its properties can be leveraged to develop advanced materials for use in light-based electronic devices, such as sensors, displays, and communication technologies.

Synthetic route

3,6-dibromo-9-hexyl-9H-carbazole (150623-72-6) + bis(pinacol)diborane (73183-34-3) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
With potassium acetate; palladium dichloride In N,N-dimethyl-formamide at 110℃; for 24h;	72%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 85℃; for 12h; Inert atmosphere;	60%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 85℃; for 12h;	59.6%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 60℃; Inert atmosphere;
With potassium acetate; Pd(II)(dppf) In N,N-dimethyl-formamide for 12h; Miyaura Borylation Reaction; Inert atmosphere; Reflux; Sealed tube;

3,6-dibromo-9-hexyl-9H-carbazole (150623-72-6) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
Stage #1: 3,6-dibromo-9-hexyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃;	64%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 3,6-diiodo-9-hexyl-9H-carbazole (156972-66-6) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,4-dioxane at 90℃; Inert atmosphere;	44%

3,6-dibromo-9H-carbazole (6825-20-3) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / toluene; water 2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C View Scheme

1-bromo-hexane (111-25-1) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; potassium hydroxide / toluene; water 2: palladium dichloride; potassium acetate / N,N-dimethyl-formamide / 24 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 40 °C 3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 12 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 12 h / 40 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere View Scheme

9H-carbazole (86-74-8) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 40 °C 3.1: potassium acetate; bis-triphenylphosphine-palladium(II) chloride / dimethyl sulfoxide / 12 h / 85 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 48 h / 20 °C 2.1: N-Bromosuccinimide / chloroform / 12 h / 40 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere View Scheme

N-hexylcarbazole (4041-21-8) → 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / chloroform / 12 h / 40 °C 2: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere View Scheme

5-bromo-2-thiophencarboxaldehyde (4701-17-1) + 9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8) → 5,5’-(9-hexyl-9H-carbazole-3,6-diyl)bis(thiophene-2-carbaldehyde) (1383124-67-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 24h;	77%

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8) + (6R,6'R,8R,8'R)-3,3'-(4-bromopyridine-2,6-diyl)bis(7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoisoquinoline) → C76H79N7

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene; tert-butyl alcohol at 80℃; for 48h; Schlenk technique;	43%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene; tert-butyl alcohol at 80℃; for 48h; Inert atmosphere; Sealed tube;	43%

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8) + C26H24BrNS2 (1519104-49-4) → C70H67N3S4 (1519104-41-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	23%

9-hexyl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (628336-95-8) + 4-(7-bromo-9,9-dioctyl-9H-fluoren-2-yl)benzonitrile (1261172-47-7) → C90H107N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 110℃; Inert atmosphere;

Upstream product

• 4041-21-8 N-hexylcarbazole 
• 86-74-8 9H-carbazole 
• 111-25-1 1-bromo-hexane 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 150623-72-6 3,6-dibromo-9-hexyl-9H-carbazole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 156972-66-6 3,6-diiodo-9-hexyl-9H-carbazole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Conjugated polymers containing a 2,2′-biimidazole moiety - A novel fluorescent sensing platform

Two novel conjugated polymers containing a 2,2′-biimidazole moiety have been designed, synthesized, and demonstrated to be used as an effective fluorescent sensing platform for detection of Ag+ and cysteine. This is the first example utilizing a fluorescent conjugated polymer-Ag+ complex to selectively detect Cys with a nanomolar range detection limit.

Nonlinear Optical Studies of Conjugated Organic Dyes for Optical Limiting Applications

D-π-A conjugated organic dyes made of different donor/acceptor moieties namely Hexylcarbazole (HC), 4,7- Dithiophene-2-yl) benzo[c][1,2,5]thiadiazole (DTBT) and Poly-4-(5-(9-Hexyl-9H-carbazol-2-yl)thiophen-2-yl)benzo[c][1,2,5]thiadiazole (PCTB) were prepared by coupling reactions. FTIR, NMR, and mass spectrometry were used to determine the molecular structure of synthesized compounds. Both HC and DTBT show a wide optical transmittance window (400-600 nm) with absorption maxima in the UV region. However, PCTB shows an altered band structure with a broad absorption in the visible domain (448 nm). Density functional theory (DFT) calculations expose that the bandgap between HOMO and LUMO decreases as the conjugation extends, and redshift occurs in UV-Vis absorption spectra. The emission spectrum of PCBT shows strong emission maxima at 541 nm with the corresponding large Stokes shift 3837 cm?1 due to its enhanced charge transfer property in the excited state. Nonlinear optical absorption was studied by open-aperture Z-scan technique using Nd:YAG laser (532 nm, 10 Hz, 9 ns). Here HC, DTBT exhibit a genuine two-photon absorption (TPA) process while PCTB possesses sequential TPA involving excited-state absorption. All dyes exhibit energy-absorbing optical limiting behaviour ascribed due to the two-photon absorption process. Among the investigated dyes, PCTB polymer shows a higher TPA coefficient (1.22 × 10?10 m/W) and a lower onset optical limiting threshold (1.06 × 1012 W/m2). Thus, the tunability of band structure and nonlinearity with a change in the molecular arrangement was successfully demonstrated in thiophene-benzothiadiazole-based organic dyes.

Pinene condensed chiral terpyridyl bidentate compound and preparation method thereof

The invention discloses a pinene condensed chiral terpyridyl bidentate compound and a preparation method thereof. The compound has a structure formula shown in the description. Commercial diethyl oxalate and acetone are adopted as initial raw materials, the initial raw materials are subjected to a Suzuki coupling reaction with a boronic acid pinacol ester compound, and thus a chirally modified terpyridyl bidentate ligand is synthesized. The synthesis method disclosed by the invention is simple in operation, and the raw materials are low in price and easy to obtain. A terpyridyl compound can beused as the tridentate ligand to form a stable complex together with multiple transition metals and rare earth metal ions, and in addition, the complex has good catalysis performance and special redox, photophysical properties, and the like, and can be applied to fields such as material science, life science, supramolecular self assembling, molecular catalysis and DNA (deoxyribonucleic acid) chips.

Ditopic Chiral Pineno-Fused 2,2′:6′,2″-Terpyridine: Synthesis, Self-Assembly, and Optical Properties

The syntheses of 4′-substituted chiral 2,2′:6′,2″-terpyridine (tpy) ligands with predetermined configurations and directionalities are rather limited in the supramolecular chemistry field. In this study, a carbazole-linked ditopic chiral ligand L was synthesized using 4′-bromo-substituted pineno-fused tpy 5 as the precursor. Upon complexation with Cd(NO3)2·4H2O and Zn(NO3)2·6H2O, two enantiomerically pure metallosupramolecules, [Cd3L3] and [Zn4L4], have been self-assembled and characterized by NMR, electrospray ionization-mass spectrometry, traveling wave ion mobility-mass spectrometry, and DOSY analysis. In addition, their optical properties are characterized by UV-vis, fluorescence, circular dichroism, and circularly polarized luminescence, suggesting an efficiency transmission and amplification of chirality from the ligand to metal center via self-assembly.

Organic blue fluorescent material and preparation method thereof and organic electroluminescent device

The invention discloses an organic blue fluorescent material and a preparation method thereof and an organic electroluminescent device. The organic blue fluorescent material has the following generalmolecular formulas shown as formula I, formula II, formula III or formula IV: formula I is D-pi-A, formula II is A-pi-D-pi-A, formula III (Please see the specification for the formula), and formula IV(Please see the specification for the formula), wherein D represents an electron donor group of the organic blue fluorescent material, pi represents an intermediate connection pi bridge group of theorganic blue fluorescent material, and A represents an electron acceptor group of the organic blue fluorescent material. The organic blue fluorescent material has good blue luminescent properties, theorganic electroluminescent device prepared from the organic blue fluorescent material used as the luminescent layer exhibits high-quality deep blue light emitting performance, the device efficiency is stable, no obvious efficiency roll-off phenomenon is caused, and the device has high maximum external quantum efficiency.

Metal-free organic luminophores with ultrastrong dipole moment exhibiting force-induced near-infrared emission (>800 nm) turn-on

Two metal-free organic luminophores with ultrastrong dipole moments of 16.1 (CPBT) and 22.7 (CTBT) Debye were developed for constructing near-infrared mechanoresponsive luminescent materials. Amorphous CTBT showed a remarkable emission turn-on peak at 822 nm due to disturbance in the dipole-dipole interactions in the solid state upon mechanical grinding.

Iridium complex grafted to 3,6-carbazole-alt-tetraphenylsilane copolymers for blue electrophosphorescence

We designed a 3,6-dibromo-9-hexyl-9H-carbazole derivative with the blue emissive iridium complex bis[2-(4,6-difluorophenyl)pyridyl-N,C 2′](picolinato)iridium(III) (Flrpic) linked at the alkyl terminal. Based on this monomer, novel 3,6-carbazole-alt-tetraphenylsilane copolymers grafted with Flrpic were synthesized by palladium-catalyzed Suzuki coupling reaction, and the content of Flrpic in the polymers could be controlled by feed ratio of the monomers. The polymer films mainly show blue emission from Flrpic, and the emission intensity from the polymer backbones is much weaker compared with the doped analogues, which demonstrates an efficient energy transfer from polymeric host to covalently bonded guest. The phase separation in the polymers was suppressed, which can be identified by atomic force microscopy and designed electroluminescent (EL) devices. EL devices based on the polymers exhibited blue phosphorescence from Flrpic. The luminous efficiency of preliminary devices reached 2.3 cd/A, and the efficiency roll-off at high current densities was suppressed.