Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2,7-Carbazole Derived Organoboron Compounds: Synthesis and Molecular Fluorescence.

ABSTRACT: Triarylboranes have drawn much attention in OLEDs owing to their remarkable solid-state luminescence properties. Here two new A-D-A type compounds, 2,7-bis(dimesitylboryl)-N-ethyl-carbazole (BCz) using triarylborane as electron acceptor and carbazole as electron donor while 2,7-bis((4-(dimesitylboryl)phenyl)ethynyl)-9-ethyl-carbazole (BPACz) using phenylacetylene as extra conjugated bridge, have been synthesized and their photoluminescence related properties in various states have been investigated both experimentally and theoretically. Both compounds show blue emission with high quantum yields, being potential candidates for blue OLED materials.

SUBMITTER: Chen M

PROVIDER: S-EPMC8568956 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2,7-Carbazole Derived Organoboron Compounds: Synthesis and Molecular Fluorescence.

Chen Minhui M Wei Juan J Zhang Yufeng Y Wu Lin L Tan Leibo L Shi Shanglong S Shi Junqing J Ji Lei L

Frontiers in chemistry 20211022

Triarylboranes have drawn much attention in OLEDs owing to their remarkable solid-state luminescence properties. Here two new A-D-A type compounds, 2,7-bis(dimesitylboryl)-N-ethyl-carbazole (BCz) using triarylborane as electron acceptor and carbazole as electron donor while 2,7-bis((4-(dimesitylboryl)phenyl)ethynyl)-9-ethyl-carbazole (BPACz) using phenylacetylene as extra conjugated bridge, have been synthesized and their photoluminescence related properties in various states have been investiga ...[more]

PMID: 34746094

Similar Datasets

Multifunctional organoboron compounds for scalable natural product synthesis.

Project description:Efficient catalytic reactions that can generate C-C bonds enantioselectively, and ones that can produce trisubstituted alkenes diastereoselectively, are central to research in organic chemistry. Transformations that accomplish these two tasks simultaneously are in high demand, particularly if the catalysts, substrates and reagents are inexpensive and if the reaction conditions are mild. Here we report a facile multicomponent catalytic process that begins with a chemoselective, site-selective and diastereoselective copper-boron addition to a monosubstituted allene; the resulting boron-substituted organocopper intermediates then participate in a similarly selective allylic substitution. The products, which contain a stereogenic carbon centre, a monosubstituted alkene and an easily functionalizable Z-trisubstituted alkenylboron group, are obtained in up to 89 per cent yield, with more than 98 per cent branch-selectivity and stereoselectivity and an enantiomeric ratio greater than 99:1. The copper-based catalyst is derived from a robust heterocyclic salt that can be prepared in multigram quantities from inexpensive starting materials and without costly purification procedures. The utility of the approach is demonstrated through enantioselective synthesis of gram quantities of two natural products, namely rottnestol and herboxidiene (also known as GEX1A).

| S-EPMC4267680 | biostudies-literature

2,7-Dibromo-9-octyl-9H-carbazole.

Project description:In the crystal structure of the title compound, C(20)H(23)Br(2)N, the octyl chains are extended in an anti conformation and form a segregating bilayer, isolating rows of carbazole units. The carbazole moieties are engaged in offset π-π inter-actions; the smallest centroid-to-centroid distance is 4.2822 (11) Å. This offset packing motif allows the methyl-ene group attached directly to the N atom to be involved in two short C-H⋯π inter-actions (H⋯centroid distances = 2.96 and 2.99 Å) with an adjacent carbazole. One of the Br atoms also participates in a short contact [3.5475 (3) Å] with a symmetry-related (-x, 1 - y, -z) Br atom. This value is significantly smaller than the sum of the van der Waals radii for bromine (3.70 Å).

| S-EPMC2959667 | biostudies-literature

Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence.

Project description:Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2-0.4, reaching in some cases values as high as 0.5-0.6. Laser-flash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signal.

| S-EPMC6880824 | biostudies-literature

Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices.

Project description:Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All-ortho-fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (Φfl ) of 18-24 % in solution, green or yellow solid-state emission (Φfl up to 23 %), and strong chiroptical response with large dissymmetry factors of up to 1.12×10-2 . Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting Φfl of up to 47 % in CH2 Cl2 and 25 % in the solid state. As revealed by the DFT calculations, their P-M interconversion pathway is more complex than that of H1. Single-crystal X-ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices.

| S-EPMC7898935 | biostudies-literature

2,7-Bis(2-nitro-phen-yl)-9-octyl-9H-carbazole.

Project description:The title compound, C(32)H(31)N(3)O(4), was obtained in a Suzuki coupling of carbazole diboronic acid and bromo-nitro-benzene. In the crystal, the mol-ecule adopts a non-symmetric conformation. The carbazole ring system is approximately planar [maximum deviation from the least-squares plane = 0.039?(2)?Å]. The planes of the carbazole unit and the benzene rings subtend dihedral angles of 48.42?(7) and 41.81?(6)°. The dihedral angles between the planes of the nitro-phenyl rings and the nitro groups are 44.34?(19) and 61.64?(15)°. The crystal is built from two strands of parallel mol-ecules with inter-digitated octyl chains. These strands are symmetry related by a twofold screw axis.

| S-EPMC3344178 | biostudies-literature

Synthesis and fluorescence properties of butadiyne-linked linear and cyclic carbazole oligomers.

Project description:Butadiyne-linked linear and cyclic carbazole oligomers were successfully synthesized. The intensity of the emission band in the 0-0 band of the highly planar macrocyclics decreased compared to that of the 0-1 band. Contrary to this, for larger macrocycles having reduced planarity, the intensity of the emission of the 0-0 band increased as in the cases of the linear compounds. This suggests that the emission color of the π-conjugated molecule can be controlled not only by the difference between the cyclic and chain structures but also by the control of the planarity, and is expected to be a new principle for molecular design in the development of fluorescent materials.

| S-EPMC9050127 | biostudies-literature

Crystal structure of dimethyl 9H-carbazole-2,7-di-carb-oxy-late.

Project description:In the title compound, C16H13NO4, the carbazole ring system is almost planar with non-H atoms possessing a mean deviation from planarity of 0.037 Å. The two ester groups are orientated trans to one another and tilted slightly from the mean plane of the carbazole ring system, making dihedral angles of 8.12 (6) and 8.21 (5)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds forming inversion dimers. The dimers are linked by parallel slipped π-π inter-actions, forming slabs propagating along the b-axis direction [inter-centroid distance = 3.6042 (8) Å, inter-planar distance = 3.3437 (5) Å, slippage = 1.345 Å].

| S-EPMC4647360 | biostudies-literature

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic-organic hybrid perovskite solar cells.

Project description:The ever increasing demand for clean energy has encouraged researchers to intensively investigate environmentally friendly photovoltaic devices. Inorganic-organic hybrid perovskite solar cells (PSCs) are very promising due to their potentials of easy fabrication processes and high power conversion efficiencies (PCEs). Designing hole-transporting materials (HTMs) is one of the key factors in achieving the high PCEs of PSCs. We now report the synthesis of two types of carbazole-based polymers, namely 3,6-Cbz-EDOT and 2,7-Cbz-EDOT, by Stille polycondensation. Despite the same chemical composition, 3,6-Cbz-EDOT and 2,7-Cbz-EDOT displayed different optical and electrochemical properties due to the different connectivity mode of the carbazole unit. Therefore, their performances as hole-transporting polymeric materials in the PSCs were also different. The device based on 2,7-Cbz-EDOT showed better photovoltaic properties with the PCE of 4.47% than that based on 3,6-Cbz-EDOT. This could be due to its more suitable highest occupied molecular orbital (HOMO) level and higher hole mobility.

| S-EPMC4979756 | biostudies-literature

Supported Palladium Nanoparticles Catalyzed Intermolecular Carbopalladation of Nitriles and Organoboron Compounds.

Project description:The first heterogeneous catalyzed example for the direct synthesis of aromatic ketones via intermolecular carbopalladation of aliphatic nitriles and organoboron compounds was developed. This mild method proceeds with a supported palladium nanoparticles catalyst that could be reused and recycled five times. The fresh and used catalysts were characterized by XPS and TEM. The XPS analysis indicated that Pd0 was the active species for the reaction. This methodology provides a mild and cost-effective strategy for the efficient synthesis of ketones.

| S-EPMC9124771 | biostudies-literature

Coumarin-carbazole based functionalized pyrazolines: synthesis, characterization, anticancer investigation and molecular docking.

Project description:A series of novel pyrazoline scaffolds from coumarin-carbazole chalcones were synthesized. We explored various acetyl, amide, and phenyl substituents at the N-1 position of the pyrazoline core. The synthesized compounds were characterized by FTIR, 1H-NMR, 13C-NMR, DEPT, and mass spectroscopic techniques. The in vitro cytotoxicity study of all the synthesized compounds was evaluated against HeLa, NCI-H520 and NRK-52E cell lines. Compounds 4a and 7b became the most active compounds and exhibited their potential to arrest the cell cycle progression and induce apoptosis in both the cell lines. In addition, molecular docking studies revealed a higher binding affinity of both the molecules with CDK2 protein. Based on the obtained results, a comprehensive analysis is warranted to establish the role of compounds 4a and 7b as promising cancer therapeutic agents.

| S-EPMC9037808 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data