Synthesis of Conjugated Oligomers and Polymers via Palladium-Catalyzed Cross-Coupling: Synthesis of Conjugated Polymers for Materials Science

2003 ◽  
pp. 825-861 ◽  
Author(s):  
A. Dieter Schlüter ◽  
Zhishan Bo
Keyword(s):  
Conjugated Polymers ◽  
Materials Science ◽  
Cross Coupling ◽  
Conjugated Oligomers ◽  
Palladium Catalyzed

scholarly journals Synthesis of π-Conjugated Polymers Containing Benzotriazole Units via Palladium-Catalyzed Direct C-H Cross-Coupling Polycondensation for OLEDs Applications

Polymers ◽  
2021 ◽  
Vol 13 (2) ◽  
pp. 254
Author(s):  
Dong Han ◽  
Jingwen Li ◽  
Qiang Zhang ◽  
Zewang He ◽  
Zhiwei Wu ◽  
...  
Keyword(s):  
Conjugated Polymers ◽  
Quantum Efficiency ◽  
Cross Coupling ◽  
Building Blocks ◽  
Gravimetric Analysis ◽  
19F Nmr Spectra ◽  
Light Emitting ◽  
Molecular Weights ◽  
Palladium Catalyzed ◽  
Red Luminescence

Four D-π-A conjugated polymers, namely P1–P4, which contain benzotriazole building blocks in their backbone as acceptor, are synthesized via palladium-catalyzed direct C-H cross-coupling polycondensation of 5,6-difluorobenzotriazole with different thiophene derivatives, including 3-octylthiophene, 2,2’-bithiophene, thieno[3,4-b][1,4]dioxine, and 4,4-dioctyl-4H-silolo-[3,2-b:4,5-b’]dithiophene as donor units, respectively. Taking the polymer P1 as an example, the chemical structure of the polymer is demonstrated by 1H and 19F NMR spectra. The optical, electrochemical, and thermal properties of these polymers are assessed by UV–vis absorption and fluorescence spectroscopy, cyclic voltammetry (CV), and thermal gravimetric analysis (TGA), respectively. DFT simulations of all polymers are also performed to understand their physicochemical properties. Furthermore, P1 and P2, which have relatively higher molecular weights and better fluorescent quantum efficiency than those of P3 and P4, are utilized as lighting emitters for organic light-emitting diodes (OLEDs), affording promising green and red luminescence with 0.07% and 0.14% of maximum external quantum efficiency, respectively, based on a device with an architecture of ITO/PEDOT:PSS/PTAA/the polymer emitting layer/TPBi/LiF/Al.

scholarly journals Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes

Molecules ◽  
2020 ◽  
Vol 25 (23) ◽  
pp. 5532
Author(s):  
Laëtitia Chausset-Boissarie ◽  
Nicolas Cheval ◽  
Christian Rolando
Keyword(s):  
Organic Synthesis ◽  
Functional Group ◽  
Materials Science ◽  
Cross Coupling ◽  
High Yield ◽  
Efficient Synthesis ◽  
Mild Conditions ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Novel Strategy

Monofluoroalkenes are versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with primary and strained secondary alkylboronic acids under mild conditions. This novel strategy gives access to a wide range of functionalized tri- and tetrasubstituted monofluoroalkenes in high yield, with good functional group tolerance, independently from the gem-bromofluoroalkenes geometry.

Palladium-catalyzed carbene coupling of N-tosylhydrazones and arylbromides to synthesize cross-conjugated polymers

2019 ◽  
Vol 10 (5) ◽  
pp. 569-573 ◽  
Author(s):  
Qi Zhou ◽  
Yunpeng Gao ◽  
Yiyang Xiao ◽  
Lefei Yu ◽  
Zihao Fu ◽  
...  
Keyword(s):  
Conjugated Polymers ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
First Time

Palladium-catalyzed cross-coupling reactions of N-tosylhydrazones and arylbromides have been applied for the first time in the synthesis of cross-conjugated polymers, namely poly(arylene-1,1-vinylidene)s (iso-PAVs).

Suzuki–Miyaura cross-coupling for chemoproteomic applications

2020 ◽  
Author(s):  
Jian Cao ◽  
Ernest Armenta ◽  
Lisa Boatner ◽  
Heta Desai ◽  
Neil Chan ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Cross Coupling ◽  
Protein Profiling ◽  
Protein Labeling ◽  
Caspase 8 ◽  
Complex Cell ◽  
Bioorthogonal Chemistry ◽  
Reaction Conditions ◽  
Target Deconvolution ◽  
Palladium Catalyzed

Bioorthogonal chemistry is a mainstay of chemoproteomic sample preparation workflows. While numerous transformations are now available, chemoproteomic studies still rely overwhelmingly on copper-catalyzed azide –alkyne cycloaddition (CuAAC) or 'click' chemistry. Here we demonstrate that gel-based activity-based protein profiling (ABPP) and mass-spectrometry-based chemoproteomic profiling can be conducted using Suzuki–Miyaura cross-coupling. We identify reaction conditions that proceed in complex cell lysates and find that Suzuki –Miyaura cross-coupling and CuAAC yield comparable chemoproteomic coverage. Importantly, Suzuki–Miyaura is also compatible with chemoproteomic target deconvolution, as demonstrated using structurally matched probes tailored to react with the cysteine protease caspase-8. Uniquely enabled by the observed orthogonality of palladium-catalyzed cross-coupling and CuAAC, we combine both reactions to achieve dual protein labeling.

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