Synthesis and optical and electrochemical properties of copolymers consisting of 9,9-dihexylfluorene and aromatic triazole chromophores

Shinn Horng Chen, Yun Chen, Chuen Shiou Shiau, Cheng Jang Tsai

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Aromatic triazole chromophores were incorporated into polyfluorene in an attempt to increase electron affinity, to promote emission efficiency, and to diminish excimer formation. Poly(9,9-dihexylfluorene) (PI) and new copolymers with aromatic triazoles (P2-P4) were prepared by Suzuki coupling polymerization. In P2, the aromatic triazole (3.8 mol %) was attached exclusively as terminal groups, whereas P3 and P4 were main-chain copolymers containing 3.9 and 10.3 mol % aromatic triazole chromophores, respectively. The copolymers were soluble in common organic solvents and showed high decomposition temperatures (437-458 C). The twisted structure between the triazole and fluorene increased the emission efficiency and effectively prevented excimer formation in P2-P4. After the introduction of the triazole units, the absorption spectra showed a blueshift (from 388 to 381 nm in chloroform) due to confined conjugation, but the photoluminescence spectra remained almost the same (417-418 nm); this was attributed to oligofluorene segments. No emission of triazole fluorophores was observed because of efficient energy transfer from the triazole to oligofluorene segments. However, incomplete energy transfer was observed in CH 3COOH. The optical stability upon thermal annealing was also improved by the incorporation of aromatic triazole segments. From cyclic voltammetry results, P2-P4, containing triazole groups, showed greater electron affinity (lowest unoccupied molecular orbital level = -2.67 to -2.71 eV) than P1 (-2.52 eV). Electroluminescence devices of P1-P4 all exhibited excimer emissions (483-521 nm), which could also be diminished by the introduction of aromatic triazole chromophores.

Original languageEnglish
Pages (from-to)136-146
Number of pages11
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume45
Issue number1
DOIs
Publication statusPublished - 2007 Jan 1

Fingerprint

Triazoles
Chromophores
Electrochemical properties
Electron affinity
Copolymers
Optical properties
Energy transfer
Fluorophores
Electroluminescence
Molecular orbitals
Chlorine compounds
Organic solvents
Cyclic voltammetry
Absorption spectra
Photoluminescence
Thermodynamic stability
Polymerization
Annealing
Decomposition
Temperature

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

@article{3ccee54de0824335bf3859661681efc8,
title = "Synthesis and optical and electrochemical properties of copolymers consisting of 9,9-dihexylfluorene and aromatic triazole chromophores",
abstract = "Aromatic triazole chromophores were incorporated into polyfluorene in an attempt to increase electron affinity, to promote emission efficiency, and to diminish excimer formation. Poly(9,9-dihexylfluorene) (PI) and new copolymers with aromatic triazoles (P2-P4) were prepared by Suzuki coupling polymerization. In P2, the aromatic triazole (3.8 mol {\%}) was attached exclusively as terminal groups, whereas P3 and P4 were main-chain copolymers containing 3.9 and 10.3 mol {\%} aromatic triazole chromophores, respectively. The copolymers were soluble in common organic solvents and showed high decomposition temperatures (437-458 C). The twisted structure between the triazole and fluorene increased the emission efficiency and effectively prevented excimer formation in P2-P4. After the introduction of the triazole units, the absorption spectra showed a blueshift (from 388 to 381 nm in chloroform) due to confined conjugation, but the photoluminescence spectra remained almost the same (417-418 nm); this was attributed to oligofluorene segments. No emission of triazole fluorophores was observed because of efficient energy transfer from the triazole to oligofluorene segments. However, incomplete energy transfer was observed in CH 3COOH. The optical stability upon thermal annealing was also improved by the incorporation of aromatic triazole segments. From cyclic voltammetry results, P2-P4, containing triazole groups, showed greater electron affinity (lowest unoccupied molecular orbital level = -2.67 to -2.71 eV) than P1 (-2.52 eV). Electroluminescence devices of P1-P4 all exhibited excimer emissions (483-521 nm), which could also be diminished by the introduction of aromatic triazole chromophores.",
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Synthesis and optical and electrochemical properties of copolymers consisting of 9,9-dihexylfluorene and aromatic triazole chromophores. / Chen, Shinn Horng; Chen, Yun; Shiau, Chuen Shiou; Tsai, Cheng Jang.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 45, No. 1, 01.01.2007, p. 136-146.

Research output: Contribution to journalArticle

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T1 - Synthesis and optical and electrochemical properties of copolymers consisting of 9,9-dihexylfluorene and aromatic triazole chromophores

AU - Chen, Shinn Horng

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AU - Shiau, Chuen Shiou

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AB - Aromatic triazole chromophores were incorporated into polyfluorene in an attempt to increase electron affinity, to promote emission efficiency, and to diminish excimer formation. Poly(9,9-dihexylfluorene) (PI) and new copolymers with aromatic triazoles (P2-P4) were prepared by Suzuki coupling polymerization. In P2, the aromatic triazole (3.8 mol %) was attached exclusively as terminal groups, whereas P3 and P4 were main-chain copolymers containing 3.9 and 10.3 mol % aromatic triazole chromophores, respectively. The copolymers were soluble in common organic solvents and showed high decomposition temperatures (437-458 C). The twisted structure between the triazole and fluorene increased the emission efficiency and effectively prevented excimer formation in P2-P4. After the introduction of the triazole units, the absorption spectra showed a blueshift (from 388 to 381 nm in chloroform) due to confined conjugation, but the photoluminescence spectra remained almost the same (417-418 nm); this was attributed to oligofluorene segments. No emission of triazole fluorophores was observed because of efficient energy transfer from the triazole to oligofluorene segments. However, incomplete energy transfer was observed in CH 3COOH. The optical stability upon thermal annealing was also improved by the incorporation of aromatic triazole segments. From cyclic voltammetry results, P2-P4, containing triazole groups, showed greater electron affinity (lowest unoccupied molecular orbital level = -2.67 to -2.71 eV) than P1 (-2.52 eV). Electroluminescence devices of P1-P4 all exhibited excimer emissions (483-521 nm), which could also be diminished by the introduction of aromatic triazole chromophores.

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