Suzuki Coupling Method Research Articles

Synthesis and Opto-electrical Properties of Stellar Polyfluorene Derivatives Containing Polyhedral Oligomeric Silsesquioxanes as the Center Core

Three polyfluorene derivatives (P1–P3) emitting blue, green and red light were prepared via a Suzuki coupling method. Polyhedral oligomeric silsesquioxanes (POSS) were integrated into the center core of the derivatives to create stellar light-emitting polymers (POSS-P1–POSS-P3). The glass-transition and decomposition temperatures were raised after introducing POSS moieties. The starlike polymers showed a reduced emissive band at 540 nm when annealing at 200 °C. The result implies that integrated POSS at the center core suppresses the keto effect generally occurring for polyfluorenes. Double-layer light-emitting devices of indium tin oxide/poly(ethylenedioxythiophene)/polymer/Ca/Al were fabricated to evaluate polymer potential. Compared with pristine polymers, the maximum brightness and the current efficiency of devices using POSS-containing polymers as active layers were enhanced. A blending method using P1 or POSS-P1 as the host matrix further improved device performance.

Highly Fluorescent Contrast for Rewritable Optical Storage Based on Photochromic Bisthienylethene-Bridged Naphthalimide Dimer

A novel naphthalimide dimer tethered by a photochromic bisthienylethene bridge was synthesized by the Suzuki coupling method. Reversible, high-degree fluorescence modulation of the naphthalimide chromophore was realized by photoisomerization of the photochromic subunit in polymer matrixes, and two-dimensional recording employing different wavelengths of lights in write, read, and erase cycles was demonstrated.

Synthesis of isoelectronic polyazomethine and poly(arylene vinylene) by a palladium‐catalyzed Suzuki coupling method

AbstractTwo fully conjugated copolymers containing 2,7‐(9,9‐dioctyl) fluorene and 3,6‐(N‐hexyl‐9H‐carbazole) disubstituted rings and arylene vinylene or azomethine units in the main chain were synthesized through a palladium‐catalyzed Suzuki coupling method of 2,7‐bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)‐9,9‐dioctyl fluorene with 1,4‐bis(6‐bromo‐N‐hexyl‐9H‐carbazole‐3‐yl vinyl) benzene or N,N‐bis(6‐bromo‐N‐hexyl‐9H‐carbazole‐3‐yl methylidene) 1,4‐phenylenediamine. Bisbromine arylene vinylene and arylenazomethine monomers were synthesized by condensation of 3‐formyl‐N‐hexyl‐6‐bromo carbazole with tetraethyl‐p‐xylylene diphosphonate or 1,4‐phenylenediamine. Copolymers were characterized by FTIR, 1H‐NMR, DSC, UV‐visible and photoluminescence methods. Copyright © 2005 Society of Chemical Industry

Synthesis of polymer-iridium complex and its electroluminescent characteristics

A π-conjugated polymer-iridium complex containing the ligand in the main chain was synthesized by the Suzuki coupling method, and was applied to organic light-emitting devices (OLEDs) as the emitter material. The polymer-iridium complex showed red photoluminescence and electroluminescence with the maximum external quantum efficiency of ca. 3% by using 4,4′-N,N′-dicarbazole-biphenyl and 2-(4-biphenylyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole blended into the polymer emitter layer. Copyright © 2005 John Wiley & Sons, Ltd.

Ladder-Type Oligo(p-phenylene)s Tethered to a Poly(alkylene) Main Chain: The Orthogonal Approach to Functional Light-Emitting Polymers

We report a series of light-emitting polymers with ladder-type oligo(p-phenylene) units orthogonally and periodically tethered to a polyalkylene main chain via a substitution-type condensation polymerization reaction. This involved the reaction between lithiated fluoreneacene oligomers and a homologous series of α,ω-dibromoalkanes. The fluoreneacene oligomers were synthesized using a step-by-step procedure involving the Suzuki coupling method, Grignard reaction, and Friedel−Crafts type ring closure (alkylation). The polymerization involved lithiation of the reactive hydrogens in the middle phenyl group followed by an SN2-type condensation polymerization with the dibromoalkanes. The oligomers have spectral properties consistent with that of other ladder-type p-pheneneylene structures. The alkylene chain length influenced the luminophore aggregation and excimer formation in the solid state. These materials showed high photoluminescence efficiencies in both solution and solid state, making them good candidates as organic materials for light-emitting devices.

A Suzuki Coupling Method for Directly Introducing a Protected β-Aminoethyl Group into Arenes and Alkenes. Convenient Synthesis of Phenethyl and Homoallylic Amines

A Suzuki Coupling Method for Directly Introducing a Protected β-Aminoethyl Group into Arenes and Alkenes. Convenient Synthesis of Phenethyl and Homoallylic Amines

Poly(p-phenylene)s. Synthesis, Optical Properties, and Quantitative Analysis with HPLC and MALDI−TOF Mass Spectrometry

A series of soluble low molecular weight poly(p-phenylene)s (PPP) has been synthesized by an excess polycondensation with the Suzuki coupling method. The reaction mixture therefore only contains oligomers of an odd number of phenylene units which are terminated by bromine atoms. The mixture has been preparatively separated into monodisperse fractions of the respective oligomers of up to 17 phenylene units. The absorption and emission spectra as well as the extinction coefficient of each fraction have been measured. On the basis of these data, the effective conjugation length can be estimated to be around 11 phenylene units. The fraction xi of each oligomer in the reaction mixture has been calculated and quantified by analytical HPLC and MALDI−TOF mass spectrometry. The theoretically expected exponential decay of the fraction sizes with increasing length is found in the HPLC analysis; however, significant deviations are found if analyzed by MALDI−TOF mass spectrometry. Possible reasons for this deviation will be discussed.

Total Synthesis of (–)‐Epothilone B: An Extension of the Suzuki Coupling Method and Insights into Structure–Activity Relationships of the Epothilones

Total Synthesis of (–)‐Epothilone B: An Extension of the Suzuki Coupling Method and Insights into Structure–Activity Relationships of the Epothilones