Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups

Synthesis, optical properties and photo-crosslinking behaviors

Cheng Jang Tsai, Yun Chen

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Poly(p-phenylenevinylene) (PPV) derivatives HOPPV and COUPPV, containing hexyloxy side groups and 7-oxy-4-methylcoumarin groups via hexyloxy spacer, respectively, have been synthesized and characterized. Their optical properties were investigated with absorption and photoluminescence (PL) spectral methods. The emissions of COUPPV and model HOPPV films are similar and show peaks around 543-550 nm which is attributed to PPV backbone. Accordingly, efficient energy transfer from the 4-methylcoumarin chromophores to PPV backbone occurred readily in COUPPV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels have been estimated from their cyclic voltammograms. As compared with HOPPV (LUMO: -2.86 eV), the electron affinity of COUPPV (LUMO: -3.65 eV) was enhanced greatly by introducing 4-methylcoumarin groups. Double-layer EL devices (Al/PEDOT/COUPPV or HOPPV/ITO) revealed green electroluminescence. The photo-crosslinking behaviors of COUPPV film under ultraviolet irradiation were investigated by FT-IR and PL methods. Both C{double bond, long}C of PPV and 4-methylcoumarin dimerized to cyclobutane derivatives and lead to crosslinking of the polymers. However, COUPPV exhibited higher photo-crosslinking rate due to pendant 4-methylcoumarin chromophores. Patterned emission from PLED utilizing this effect was also demonstrated.

Original languageEnglish
Pages (from-to)1327-1335
Number of pages9
JournalReactive and Functional Polymers
Volume66
Issue number11
DOIs
Publication statusPublished - 2006 Nov 1

Fingerprint

Molecular orbitals
optical property
Crosslinking
Optical properties
Cyclobutanes
Energy Transfer
Chromophores
energy
Photoluminescence
Polymers
irradiation
polymer
Electrons
Derivatives
electron
Equipment and Supplies
Electron affinity
Electroluminescence
Energy transfer
Electron energy levels

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Polymers and Plastics
  • Materials Chemistry

Cite this

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title = "Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups: Synthesis, optical properties and photo-crosslinking behaviors",
abstract = "Poly(p-phenylenevinylene) (PPV) derivatives HOPPV and COUPPV, containing hexyloxy side groups and 7-oxy-4-methylcoumarin groups via hexyloxy spacer, respectively, have been synthesized and characterized. Their optical properties were investigated with absorption and photoluminescence (PL) spectral methods. The emissions of COUPPV and model HOPPV films are similar and show peaks around 543-550 nm which is attributed to PPV backbone. Accordingly, efficient energy transfer from the 4-methylcoumarin chromophores to PPV backbone occurred readily in COUPPV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels have been estimated from their cyclic voltammograms. As compared with HOPPV (LUMO: -2.86 eV), the electron affinity of COUPPV (LUMO: -3.65 eV) was enhanced greatly by introducing 4-methylcoumarin groups. Double-layer EL devices (Al/PEDOT/COUPPV or HOPPV/ITO) revealed green electroluminescence. The photo-crosslinking behaviors of COUPPV film under ultraviolet irradiation were investigated by FT-IR and PL methods. Both C{double bond, long}C of PPV and 4-methylcoumarin dimerized to cyclobutane derivatives and lead to crosslinking of the polymers. However, COUPPV exhibited higher photo-crosslinking rate due to pendant 4-methylcoumarin chromophores. Patterned emission from PLED utilizing this effect was also demonstrated.",
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Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups : Synthesis, optical properties and photo-crosslinking behaviors. / Tsai, Cheng Jang; Chen, Yun.

In: Reactive and Functional Polymers, Vol. 66, No. 11, 01.11.2006, p. 1327-1335.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Luminescent poly(p-phenylenevinylene) with 4-methylcoumarin side groups

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AU - Tsai, Cheng Jang

AU - Chen, Yun

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AB - Poly(p-phenylenevinylene) (PPV) derivatives HOPPV and COUPPV, containing hexyloxy side groups and 7-oxy-4-methylcoumarin groups via hexyloxy spacer, respectively, have been synthesized and characterized. Their optical properties were investigated with absorption and photoluminescence (PL) spectral methods. The emissions of COUPPV and model HOPPV films are similar and show peaks around 543-550 nm which is attributed to PPV backbone. Accordingly, efficient energy transfer from the 4-methylcoumarin chromophores to PPV backbone occurred readily in COUPPV. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels have been estimated from their cyclic voltammograms. As compared with HOPPV (LUMO: -2.86 eV), the electron affinity of COUPPV (LUMO: -3.65 eV) was enhanced greatly by introducing 4-methylcoumarin groups. Double-layer EL devices (Al/PEDOT/COUPPV or HOPPV/ITO) revealed green electroluminescence. The photo-crosslinking behaviors of COUPPV film under ultraviolet irradiation were investigated by FT-IR and PL methods. Both C{double bond, long}C of PPV and 4-methylcoumarin dimerized to cyclobutane derivatives and lead to crosslinking of the polymers. However, COUPPV exhibited higher photo-crosslinking rate due to pendant 4-methylcoumarin chromophores. Patterned emission from PLED utilizing this effect was also demonstrated.

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