Synthesis, Optical Properties, and Characterization of New Soluble Conjugated Poly(p-phenylenevinylene) Derivatives Constituted of Alternating Pyrazole and 1,3,4-Oxadiazole Moieties

En-Ming Chang; Cheng-Tien Lee; Chun-Yen Chen; Fung Fuh Wong; Mou-Yung Yeh

doi:10.1071/CH07381

RESEARCH ARTICLE

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Synthesis, Optical Properties, and Characterization of New Soluble Conjugated Poly(p-phenylenevinylene) Derivatives Constituted of Alternating Pyrazole and 1,3,4-Oxadiazole Moieties

En-Ming Chang ^A , Cheng-Tien Lee ^A , Chun-Yen Chen ^A , Fung Fuh Wong ^B ^D and Mou-Yung Yeh ^A ^C ^D

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, National Cheng Kung University, Tainan 70101, Taiwan, Republic of China.

^B Graduate Institute of Pharmaceutical Chemistry, China Medical University, Taichung 40402, Taiwan, Republic of China.

^C Sustainable Environment Research Center, National Cheng Kung University, Tainan City 709, Taiwan, Republic of China.

^D Corresponding author. Email: wongfungfuh@yahoo.com.tw

Australian Journal of Chemistry 61(5) 342-349 https://doi.org/10.1071/CH07381
Submitted: 31 October 2007 Accepted: 20 March 2008 Published: 22 May 2008

Abstract

Two new soluble poly(p-phenylenevinylene) derivatives with 1,3,4-oxadiazole and pyrazole rings along the main core were successfully synthesized by 1,3-dipolar addition, dehydration, and Heck coupling reaction. The new conjugated polymers are soluble in common organic solvents afforded by the fully conjugated backbone with soluble dedecyloxy side groups. The polymers showed relatively high glass-transition temperatures (~150°C) and good satisfactory thermal stability. Solutions of the polymers emitted bluish-green light with photoluminescence (PL) emission maxima around 530–540 nm. The PL spectrum for polymers of thin films, with a maximum at 570 nm, shows a red-shift (~35 nm) with respect to the solution spectrum. Cyclic voltammetry displayed that both conjugated polymers had reversible reduction and irreversible oxidation, making them n-type electroluminescent materials. The electron affinity of new polymers was estimated as 2.76–2.81 eV. The weight-average molecular weights (M_w) of the new soluble polymers were in the range 3400–3500.

Acknowledgements

We are grateful to the National Science Council of the Republic of China for financial support.

References

Synthesis, Optical Properties, and Characterization of New Soluble Conjugated Poly(p-phenylenevinylene) Derivatives Constituted of Alternating Pyrazole and 1,3,4-Oxadiazole Moieties

Abstract

Acknowledgements

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