478706-06-8

Usage

Uses

Used in Pharmaceutical Synthesis:
9-Octyl-3,6-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is used as a building block for the synthesis of pharmaceutical compounds due to its unique structure and reactivity. The boronic ester groups facilitate the formation of carbon-carbon bonds through Suzuki coupling, allowing for the creation of diverse and complex molecular structures.
Used in Advanced Materials Synthesis:
In the field of advanced materials, 9-Octyl-3,6-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is used as a precursor for the development of new materials with tailored properties. The octyl chain and boronic ester groups contribute to the solubility and processability of the compound, making it suitable for use in the synthesis of materials with specific characteristics, such as improved conductivity or enhanced stability.
Used in Organic Chemistry Research:
9-Octyl-3,6-bis(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is employed as a research compound in organic chemistry, particularly in the study of Suzuki coupling and the synthesis of complex organic molecules. Its unique structure and reactivity make it an interesting subject for exploring new reaction pathways and understanding the fundamental principles of organic chemistry.

Upstream product

• 4041-19-4 9-octylcarbazole 
• 111-83-1 1-bromo-octane 
• 86-74-8 9H-carbazole 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 73183-34-3 bis(pinacol)diborane 
• 79554-93-1 3,6-dibromo-9-octyl-9H-carbazole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 156028-40-9 1,4-dibromo-2,5-dioctyloxyphenylene 

Relevant academic research and scientific papers

Synthesis and sensing properties of a new carbazole fluorosensor for detection of abacavir

An abacavir-targeted fluorosensor based on the carbazole moiety has been synthesised and characterised. Recognition of abacavir is by base pairing between a uracil moiety present in the fluorosensor and the guanine moiety of abacavir. The fluorosensor exhibits five-fold quenching in the presence of 50M abacavir. Its sensitivity to abacavir is superior to that of other reverse transcriptase inhibitors: zidovudine, lamivudine and didanosine. Due to its high sensitivity, this fluorosensor has the potential to be used in multi-analyte array-based detection platforms as well as in microfluidics systems.

Novel dual BODIPY-carbazole conjugates with various linkers

Four dual BODIPY-carbazole conjugates (BDPa-d, BODIPY is 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene), with various π bridges, including none, phenyl, thiophene, and furan, were designed and synthesized. The results suggest that the π bridges have significant effect on the thermal, photophysical, and electrochemical properties of the conjugates. BDPc and BDPd, with a five-membered heterocycle as a π bridge possessing more coplanar molecular geometry, exhibit broader and red-shifted absorption with an obvious charge transfer shoulder peak, as well as red-shifted emission. UV-visible absorption spectroscopy and cyclic voltammetry results show that the extension of the π-conjugated system leads to a reduction in the optical gap with a decrease of the LUMO level. All conjugates display remarkable Stokes shifts (107-216 nm) and low fluorescence quantum yields. BDPc and BDPd, which essentially possess broad and intense absorption, and suitable HOMO-LUMO energy levels, are potential candidates for light-harvesting and photovoltaic applications.

Phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and preparation method thereof

The invention discloses a phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative and a preparation method thereof. The preparation method of the phenyl-bridged and carboxyl-terminated A1-pi-A-D-A-pi-A1 type BT derivative comprises the

Dialkyl-substituted naphtho-dioxodibenzothiophene monomer and preparation method thereof and polymer containing dialkyl-substituted naphtho-dioxodibenzothiophene unit and application of polymer

The invention discloses a dialkyl-substituted naphtho-dioxodibenzothiophene monomer and a preparation method thereof and a polymer containing a dialkyl-substituted naphtho-dioxodibenzothiophene unit and the application of the polymer. A high-absorption electron unit -SO2- exists in the dialkyl-substituted naphtho-dioxodibenzothiophene monomer, and thus the electron affinity of a molecule can be improved. Through introducing of an unsymmetrical substituting condensed ring structure and an alkyl group, the electron affinity of the monomer can be lowered, and meanwhile, solubleness of the monomer in organic solvent is improved greatly. The dialkyl-substituted naphtho-dioxodibenzothiophene monomer obtains a homopolymer or a copolymer containing the dialkyl-substituted naphtho-dioxodibenzothiophene unit through Suzuki or Stille or Yamamoto polymerization reaction, and the obtained polymer has good solubleness in the organic solvent, is suitable for solution processing, and has wide application prospects in preparation of electroluminescent devices, organic solar cells and organic field effect transistors.

The synthesis and photovoltaic properties of A-D-A-type small molecules containing diketopyrrolopyrrole terminal units

A series of novel A-D-A structured small molecule photovoltaic (PV) materials [CZ(TDPP)2, DPA(TDPP)2, PTZ(TDPP)2 and FL(TDPP)2] with diketopyrrolopyrrole (DPP) as an electron-withdrawing group were synthesized and characterized. These small molecular donors exhibit excellent solubility in common organic solvents. The density functional theory (DFT) calculations demonstrated the intramolecular charge transfer (ICT) behavior of the synthesized PV materials and an efficient charge separation was observed by a fluorescence quenching experiment. In addition, their photophysical and electrochemical properties show that they harvest sunlight over the entire visible spectrum range and keep appropriate energy levels to satisfy the requirement of solution-processable OSCs. Therefore, we explored the PV properties of the synthesized donors by fabricating BHJ solar cells with a typical structure of ITO/PEDOT:PSS/Donors: PC61BM/LiF/Al. Among them, CZ(TDPP)2 revealed a promising performance in PV devices with a power conversion efficiency (PCE) of 1.50%, along with an open-circuit voltage (VOC) of 0.66 V, a short-circuit current density (JSC) of 4.12 mA cm-2, and a fill factor (FF) of 0.44, under an illumination of AM 1.5G (80 mW cm-2).

Anchoring stability and photovoltaic properties of new D(-π-A) 2 dyes for dye-sensitized solar cell applications

This study deals with the synthesis and characterization of two new di-anchoring dyes for applications in dye-sensitized solar cells. The materials were designed with a branched D(-π-A)2 structure containing (i) a rigid alkyl-functionalized carbazole core as the donor part, (ii) one (DYE1) or two (DYE2) thiophene units as the π-bridge and (iii) a cyano-acrylic moiety as acceptor and anchoring part. Electrochemical impedance spectroscopy indicated that the injected electron lifetime is higher in the case of DYE2, probably due to the length of the π-spacer that, in combination with the alkyl chain on the carbazole unit, hampers the charge recombination with the electrolyte. Stability tests on TiO2-sensitized films revealed that the di-anchoring remarkably slows down the desorption process, which conversely is evident for classic reference dyes. The highest power conversion efficiency reaches 5.01% in the case of DYE2 with a photovoltage of 0.70 V and a photocurrent of 10.52 mA cm-2, substantially deriving from a broader absorption with respect to DYE1, as also confirmed by IPCE measurements. These results support the efforts aimed at the structural engineering of D(-π-A)2 dyes to design new, more efficient and stable organic sensitizers.

Molecular recognition of the antiretroviral drug abacavir: Towards the development of a novel carbazole-based fluorosensor

Due to their optical and electro-conductive attributes, carbazole derivatives are interesting materials for a large range of biosensor applications. In this study, we present the synthesis routes and fluorescence evaluation of newly designed carbazole fluorosensors that, by modification with uracil, have a special affinity for antiretroviral drugs via either Watson-Crick or Hoogsteen base pairing. To an N-octylcarbazole-uracil compound, four different groups were attached, namely thiophene, furane, ethylenedioxythiophene, and another uracil; yielding four different derivatives. Photophysical properties of these newly obtained derivatives are described, as are their interactions with the reverse transcriptase inhibitors such as abacavir, zidovudine, lamivudine and didanosine. The influence of each analyte on biosensor fluorescence was assessed on the basis of the Stern-Volmer equation and represented by Stern-Volmer constants. Consequently we have demonstrated that these structures based on carbazole, with a uracil group, may be successfully incorporated into alternative carbazole derivatives to form biosensors for the molecular recognition of antiretroviral drugs. The Author(s) 2011. This article is published with open access at Springerlink.com.

ELECTRON DONATING ORGANIC MATERIAL, MATERIAL FOR PHOTOVOLTAIC ELEMENT, AND PHOTOVOLTAIC ELEMENT

The invention aims at providing a photovoltaic device with high photoelectric conversion efficiency. The aim is attained by an electron donating organic material containing a benzothiadiazole compound in which (a) a benzothiadiazole skeleton and an oligothiophene skeleton are contained, (b) a band gap (Eg) is 1.8 eV or less, and (c) the level of the highest occupied molecular orbital (HOMO) is -4.8 eV or less, wherein said benzothiadiazole compound is formed by covalently combining the benzothiadiazole skeleton and the oligothiophene skeleton alternately, the proportion between the benzothiadiazole skeleton and the oligothiophene skeleton is within a range of 1:1 to 1:2 (however, excluding 1:1), and the number of thiophene rings contained in an oligothiophene skeleton is 3 or more and 12 or less.