Poly(phenylene vinylene)-Based Copolymers Containing 3,7-Phenothiazylene and 2,6-Pyridylene Chromophores

Fluorescence Sensors for Acids, Metal Ions, and Oxidation

Tzi Yi Wu, Yun Chen

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

A novel copolymer, poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-2,6-pyri-dylene-1,2-ethenylene) (P3), containing AT-hexyl-3,7-phenothiazylene and 2,6-pyridylene chromophores was synthesized to investigate the effect of protonation, metal complexation, and chemical oxidation on its absorption and photoluminescence (PL). Poly(N-hexyl-3,8-iminodibenzyl-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) and poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) (P2), consisting of 1,3-divinyl-benzene alternated with N-hexyl-3,8-iminodibenzyl and N-hexyl-3,7-phenothiazylene, respectively, were also prepared for comparison. Electrochemical investigations revealed that P3 exhibited lower band gaps (2.34 eV) due to alternating donor and acceptor conjugated units (push-pull structure). The absorption and PL spectral variations of P3 were easily manipulated by protonation, metal chelation, and chemical oxidation. P3 displayed significant bathochromic shifts when protonated with trifluoroacetic acid in chloroform. The complexation of P3 with Fe3+ led to a significant absorption change and fluorescence quenching, and this implied the coordination of ferric ions with the 2,6-pyridylene groups in the backbone. Moreover, both phenothiazylene-containing P2 and P3 showed conspicuous PL quenching with a slight redshift when oxidized with NOBF4.

Original languageEnglish
Pages (from-to)1272-1284
Number of pages13
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume42
Issue number5
DOIs
Publication statusPublished - 2004 Mar 1

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Chromophores
Metal ions
Photoluminescence
divinyl benzene
Copolymers
Fluorescence
Protonation
Complexation
Oxidation
Acids
Quenching
Sensors
Metals
Trifluoroacetic acid
Trifluoroacetic Acid
Chloroform
Chlorine compounds
Chelation
Benzene
Energy gap

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

@article{81b8ec8899944b538241b2506b3231c7,
title = "Poly(phenylene vinylene)-Based Copolymers Containing 3,7-Phenothiazylene and 2,6-Pyridylene Chromophores: Fluorescence Sensors for Acids, Metal Ions, and Oxidation",
abstract = "A novel copolymer, poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-2,6-pyri-dylene-1,2-ethenylene) (P3), containing AT-hexyl-3,7-phenothiazylene and 2,6-pyridylene chromophores was synthesized to investigate the effect of protonation, metal complexation, and chemical oxidation on its absorption and photoluminescence (PL). Poly(N-hexyl-3,8-iminodibenzyl-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) and poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) (P2), consisting of 1,3-divinyl-benzene alternated with N-hexyl-3,8-iminodibenzyl and N-hexyl-3,7-phenothiazylene, respectively, were also prepared for comparison. Electrochemical investigations revealed that P3 exhibited lower band gaps (2.34 eV) due to alternating donor and acceptor conjugated units (push-pull structure). The absorption and PL spectral variations of P3 were easily manipulated by protonation, metal chelation, and chemical oxidation. P3 displayed significant bathochromic shifts when protonated with trifluoroacetic acid in chloroform. The complexation of P3 with Fe3+ led to a significant absorption change and fluorescence quenching, and this implied the coordination of ferric ions with the 2,6-pyridylene groups in the backbone. Moreover, both phenothiazylene-containing P2 and P3 showed conspicuous PL quenching with a slight redshift when oxidized with NOBF4.",
author = "Wu, {Tzi Yi} and Yun Chen",
year = "2004",
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T1 - Poly(phenylene vinylene)-Based Copolymers Containing 3,7-Phenothiazylene and 2,6-Pyridylene Chromophores

T2 - Fluorescence Sensors for Acids, Metal Ions, and Oxidation

AU - Wu, Tzi Yi

AU - Chen, Yun

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N2 - A novel copolymer, poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-2,6-pyri-dylene-1,2-ethenylene) (P3), containing AT-hexyl-3,7-phenothiazylene and 2,6-pyridylene chromophores was synthesized to investigate the effect of protonation, metal complexation, and chemical oxidation on its absorption and photoluminescence (PL). Poly(N-hexyl-3,8-iminodibenzyl-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) and poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) (P2), consisting of 1,3-divinyl-benzene alternated with N-hexyl-3,8-iminodibenzyl and N-hexyl-3,7-phenothiazylene, respectively, were also prepared for comparison. Electrochemical investigations revealed that P3 exhibited lower band gaps (2.34 eV) due to alternating donor and acceptor conjugated units (push-pull structure). The absorption and PL spectral variations of P3 were easily manipulated by protonation, metal chelation, and chemical oxidation. P3 displayed significant bathochromic shifts when protonated with trifluoroacetic acid in chloroform. The complexation of P3 with Fe3+ led to a significant absorption change and fluorescence quenching, and this implied the coordination of ferric ions with the 2,6-pyridylene groups in the backbone. Moreover, both phenothiazylene-containing P2 and P3 showed conspicuous PL quenching with a slight redshift when oxidized with NOBF4.

AB - A novel copolymer, poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-2,6-pyri-dylene-1,2-ethenylene) (P3), containing AT-hexyl-3,7-phenothiazylene and 2,6-pyridylene chromophores was synthesized to investigate the effect of protonation, metal complexation, and chemical oxidation on its absorption and photoluminescence (PL). Poly(N-hexyl-3,8-iminodibenzyl-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) and poly(N-hexyl-3,7-phenothiazylene-1,2-ethenylene-1,3-phenylene-1,2-ethenylene) (P2), consisting of 1,3-divinyl-benzene alternated with N-hexyl-3,8-iminodibenzyl and N-hexyl-3,7-phenothiazylene, respectively, were also prepared for comparison. Electrochemical investigations revealed that P3 exhibited lower band gaps (2.34 eV) due to alternating donor and acceptor conjugated units (push-pull structure). The absorption and PL spectral variations of P3 were easily manipulated by protonation, metal chelation, and chemical oxidation. P3 displayed significant bathochromic shifts when protonated with trifluoroacetic acid in chloroform. The complexation of P3 with Fe3+ led to a significant absorption change and fluorescence quenching, and this implied the coordination of ferric ions with the 2,6-pyridylene groups in the backbone. Moreover, both phenothiazylene-containing P2 and P3 showed conspicuous PL quenching with a slight redshift when oxidized with NOBF4.

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