Synthesis and properties of poly(arylenevinylene)s comprising of an electron-donating carbazole unit and an electron-accepting 2,1,3-benzothiadiazole

Two new soluble arylenevinylene-based polymers comprising of an electron-donating carbazole unit and an electron-accepting 2,1,3-benzothiadiazole (or fluorenone) unit in the main chain were synthesized by Heck polycondensation between 3,6-divinylene-9-decyl carbazole and 4,7-dibromo-2,1,3-benzothiadiazole (or 2,7-dibromofluorenone). In the toluene solution, a polymer with benzothiadiazole unit showed strong red photoluminescence, whereas the polymer with fluorenone unit showed white–yellow photoluminescence. The polymers had good thermal stability with 5 wt% loss temperature of more than 430 °C. Electrochemically, the polymers appeared to be reversible under reduction.

Polymer Volume 46, Issue 25, 28 November 2005, Pages 11927-11933

Alternating poly(pyridyl vinylene phenylene vinylene)s: synthesis and solid state organizations

Poly(pyridyl vinylene phenylene vinylenes) were synthesized by Heck coupling procedures. These materials display large red shifts in their optical absorption which upon protonation or alkylation of the pyridyl nitrogen. Some of the polymers were found to be liquid crystalline. The protonated or alkylated versions exhibit highly organized structures due to charge-transfer interactions between polymer chains.

doi:10.1016/S0040-4020(97)00975-7

A New Family of Highly Emissive Soluble Poly(p-phenylene vinylene) Derivatives. A Step toward Fully Conjugated Blue-Emitting Poly(p-phenylene vinylene

J. Am. Chem. Soc., 120 (1), 231 -232, 1998.

Donor-acceptor copolymers for red- and near-infrared-emitting polymer light-emitting diodes

We report a comparative study of two organic soluble, vinylene-based, alternating donor-acceptor copolymers with 1,4-(2,5-dihexadecyloxyphenylene) as the donor; the acceptor is either a 2,5-linked pyridine or a 5,8-linked 2,3-diphenylpyrido[3,4-b]pyrazine. The polymers are synthesized via a Heck coupling methodology from a dihalo monomer and a divinyl monomer to yield number-average molecular weights of 16,000 g/mol for the pyridine polymer (PPyrPV) and 6500 g/mol for the pyridopyrazine polymer (PPyrPyrPV), with high solubility in common chlorinated solvents and lower solubility in less polar solvents (e.g., tetrahydrofuran). Thin-film measurements show band gaps of 2.2 and 1.8 eV for PPyrPV and PPyrPyrPV, respectively. Both polymers exhibit photoluminescence in solution and in the solid state and exhibit electroluminescence when incorporated into light-emitting diodes. In this case, a broad red emission centered at 690 nm for PPyrPV and a near-infrared emission centered at 800 nm for PPyrPyrPV have been observed

J. Polym. Sci. A Polym. Chem. Vol.43, 7 Pages: 1417-1431

Synthesis of conjugated copolymers containing phenothiazinylene vinylene moieties and their electrooptic properties

Design, Synthesis, and Electroluminescent Property of CN-Poly(dihexylfluorenevinylene) for LEDs

A new green electroluminescence polymer, CN-poly(dihexylfluorenevinylene) (CN-PDHFV), which denotes poly[(9,9-dihexyl-9H-fluorene-2,7-diyl)(1-cyanoethene-1,2-diyl)(9,9-dihexyl-9H-fluorene-2,7-diyl)(2-cyaoethene-1,2-diyl)], was synthesized by condensation polymerization utilizing the Knoevenagel reaction. The resulting polymer exhibits good solubility in common organic solvents such as chloroform, THF, and ODCB. The polymer is also easily cast on a glass plate to green film. The UV-vis spectrum of the polymer exhibits characteristically a broad absorption band at 440 nm. This polymer shows photoluminescence around max = 535 nm (exciting wavelength 410 nm) and green electroluminescence around max = 530 nm. The current-voltage-luminance (I-V-L) characteristics of the polymer show a turn-on voltage of 4.8 V and a brightness of 600 cd/m2 at 5.8 V in the Al/polymer/PEDOT/ITO device. The highest efficiency was observed to be 0.85 lm/W at 5.6 V.

Macromolecules, 36 (19), 6970 -6975, 2003.

Stereoselective Hydroboration of Diynes and Triyne to Give Products Containing Multiple Vinylene Bridges: A Versatile Application to Fluorescent Dyes

Organometallics, 23 (20), 4569 -4575, 2004.