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Usage

Uses

Used in Organic Electronic Materials:
3,6-Diethynylcarbazole is utilized as a key component in the development of organic light-emitting diodes (OLEDs) and organic photovoltaic devices. Its high thermal stability and electron-transporting properties make it an ideal candidate for enhancing the performance and reliability of these devices.
Used in Optoelectronic Devices:
3,6-Diethynylcarbazole is also studied for its potential applications in optoelectronic devices, where its unique properties can contribute to the advancement of technology in this field.
Used in Sensing Materials:
3,6-Diethynylcarbazole has been explored for its use in sensing materials, capitalizing on its chemical and physical characteristics to detect or respond to various stimuli.
Used as a Reagent in Organic Synthesis:
Furthermore, 3,6-Diethynylcarbazole serves as a reagent in organic synthesis, facilitating the creation of new compounds and materials with potential applications across different industries.

Upstream product

• 1233502-91-4 3,6-bis((trimethylsilyl)ethynyl)-9H-carbazole 
• 57103-02-3 3,6-diiodocarbazole 
• 1066-54-2 trimethylsilylacetylene 
• 86-74-8 9H-carbazole 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 1304628-08-7 C₂₂H₂₁NO₂ 

Downstream Products

• 1304628-09-8 3,6-bis[2-(4-nitrophenyl)-ethynyl]-9H-carbazole 

Relevant academic research and scientific papers

A Competitive Pull-Down Assay Using G-quadruplex DNA Linked Magnetic Nanoparticles to Determine Specificity of G-quadruplex Ligands

Herein, we develop a competitive screening method in which G-quadruplex DNA linked magnetic nanoparticles pull down selective ligands for a particular quadruplex topology from a series of small molecules. The screening strategy is first optimized with known G-quadruplex ligands and then used with a new series of G-quadruplex interactive bis-triazolyl ligands that are synthesized by Cu(I)-catalyzed azide-alkyne cycloaddition. The assay enables the identification of c-MYC and BCL2 G-quadruplex selective bis-triazole ligands that specifically target promoter G-quadruplexes in cancer cells.

Coordination-driven self-assembly of metallamacrocycles via a new Pt II2 organometallic building block with 90° geometry and optical sensing of anions

A new PtII 2 organometallic building block with 90° geometry, 3,6-bis[trans-platinum(triethylphosphine)2(nitrate) (ethynyl)]carbazole (5), containing an ethynyl functionality is synthesized in reasonable yield by employing a Sonagashira coupling reaction. Multinuclear NMR and electrospray ionization mass spectrometry (ESI-MS) including a single-crystal X-ray diffraction study characterized this 90° building unit. The self-assembly of 5 with three flexible ditopic donors (La-L c) afforded [2 + 2] metallamacrocycles (6a-c) [where La = 1,3-bis(4-pyridyl)isophthalamide; Lb = 1,3-bis(3-pyridyl) isophthalamide, and Lc = 1,2-di(4-pyridyl)ethane]. All three [2 + 2] self-assembled macrocycles were characterized by various spectroscopic techniques, and the molecular structure of 6a was determined by the single-crystal X-ray diffraction method. The square-type macrocycle 6a was designed using amide-based ligand La to make it a suitable system composed of a fluorophorereceptor combination. The amide functional group is the receptor site for the anions, which can bind through hydrogen-bonding interaction, whereas the carbazole-based 90° building unit is the fluorophore unit. Macrocycle 6a was found to be fluorescent in nature and showed dramatic fluorescence enhancement in a DMF/H2O solvent mixture upon titration with P2O74-, which plays important roles in various biological functions such as energy transduction in organisms and controls metabolic processes by participating in various enzymatic reactions. Interestingly, the nonresponsive nature of the fluorescence intensity of 6a upon addition of the anions F-, ClO4-, and H2PO4- makes it a suitable fluorescent sensor for pyrophosphate anion (P2O74-).

Selective hydration of electron-rich aryl-alkynes by a schrock-type molybdenum alkylidene catalyst

We present herein the regioselective hydration of electron-rich aryl-alkynes in presence of a Schrocktype molybdenum alkylidene catalyst. The structures of the obtained ketones were confirmed by NMR spectroscopy and HRMS as well as by single-crystal X-ray diffraction. We found out that in our conditions the hydration reaction is efficient only for aryl-alkynes and their reactivity is highly dependent on the electronic nature of the substituents on the aryl group.

Heteroaryl-linked norbornadiene dimers with redshifted absorptions

Development of Molecular Solar Thermal (MOST) systems for harvesting and storing solar energy is based on molecular photoswitches that undergo photoisomerizations to metastable isomers. One challenge is to achieve low-molecular weight molecules that absorb at sufficiently long wavelengths to match the solar spectrum. Here we show that this can be achieved by linking two norbornadiene (NBD) photoswitches to a central heterocycle, thiophene or carbazole, via alkyne appendages. In this approach, the same heteroaryl is used to tune the properties of two photoswitches at the same time, thereby keeping the molecular weight as low as possible. A series of NBD dimers was prepared by Sonogashira coupling reactions, and these compounds showed remarkable redshifted absorptions, with onsets of absorption as high as 468 nm, and thermal half-lives ranging from 44 seconds to 16 hours.

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.

Experimental and Theoretical Investigation for the Level of Conjugation in Carbazole-Based Precursors and Their Mono-, Di-, and Polynuclear Pt(II) Complexes

A series of trimethylsilyl-protected monoalkynes (Me3SiC≡C-R) and bis-alkynes (Me3 SiC≡C-R-C≡CSiMe3) incorporating carbazole spacer groups (R = carbazole-2-yl, carbazole-3-yl, carbazole-2,7-diyl, N-(2-ethylhexyl)carbazole-2,7-diyl, carbazole-3,6-diyl, N-(2-ethylhexyl)carbazole-3,6-diyl), together with the corresponding terminal monoalkynes (H-C≡C-R) and bis-alkynes (H-C≡C-R-C≡C-H), have been synthesized and characterized. The CuI-catalyzed dehydrohalogenation reaction between trans-[(Ph)(Et3P)2PtCl], trans-[(Et3P)2PtCl2], and trans-[(PnBu3)2PtCl2] and the terminal alkynes in iPr2NH/CH2Cl2 affords a series of Pt(II) mono- and diynes, while the dehydrohalogenation polycondensation reactions with trans-[(PnBu3)2PtCl2] under similar reaction conditions yields four Pt(II) poly-ynes of the form trans-[(PnBu3)2Pt-C≡C-R-C≡C-]n. The acetylide-functionalized carbazole ligands and the mono-, di-, and polynuclear Pt(II) σ-acetylide complexes have been characterized spectroscopically, with a subset analyzed using single-crystal X-ray diffraction. The Pt(II) mono-, di-, and poly-ynes incorporating the carbazole spacers are soluble in common organic solvents, and solution absorption spectra show a consistent red-shift between the 2- and 2,7- as well as 3- and 3,6-carbazole complexes. Computational modeling is used to explain the observed spectral shifts, which are related to the enhanced electronic delocalization in the latter systems. These results also indicate that the inclusion of carbazole-2,7-diyl units into rigid-rod organometallic polymers should enhance electronic transport along the chains.

Novel photoinitiator with a radical quenching moiety for confining radical diffusion in two-photon induced photopolymerization

We designed and synthesized a novel two-photon induced photoinitiator with radical quenching moiety, 3,6-bis[2-(4-nitrophenyl)-ethynyl]-9-(4-methoxybenzyl) -carbazole (BNMBC), and successfully demonstrated its optical properties, high initiating efficiency in two-photon induced polymerization (TPIP) and capability to fabricate 3D structures with high resolution. The high resolution in TPIP using BNMBC was achieved as compared to the reported photoinitiator 3,6-bis[2-(4-nitrophenyl)-ethynyl]-9-benzylcarbazole (BNBC). BNMBC was confirmed to have a large two-photon absorption cross-section of 2367 GM by Z-scan measurement. We investigated the photopolymerization properties of resins R 1-R3 in which BNBC, BNBC/phenyl methyl ether (PhOMe) and BNMBC were used as photoinitiators, respectively. The TPIP fabrication experiments exhibited that BNMBC possessed high TPIP initiating efficiency and an effective radical quenching effect. The volumes of polymer fibers fabricated by the TPIP of the photoresist using BNMBC as the photoinitiator were decreased to 20%-30% of those synthesised using BNBC as a photoinitiator. The introduction of a radical quenching group to the photoinitiator resulted in the effective confining effect of radical diffusion compared to the addition of the same molar ratio of radical quencher. This kind of photoinitiator with radical quenching group should benefit the fabrication of precise structures. The Royal Society of Chemistry.