Pyrene functional poly(vinyl alcohol) by "click" chemistry

Bahadir N. Gacal; Banu Koz; Burcin Gacal; Baris Kiskan; Matem Erdogan; Yusuf Yagci

doi:10.1002/pola.23240

Pyrene functional poly(vinyl alcohol) by "click" chemistry

Bahadir N. Gacal, Banu Koz, Burcin Gacal, Baris Kiskan, Matem Erdogan, Yusuf Yagci^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

64 Citations (Scopus)

Abstract

Side-chain pyrene functional poly(vinyl alcohol) (PVA) was synthesized by using "click chemistry" strategy. First, partial tosylation of PVA with p-toluene sulfonyl chloride were performed. The resulting PVA-Ts polymer was then quantitatively converted into poly(vinyl alcohol)-azide (PVA-N ₃) in the presence of NaN₃/DMF at 60°C. Propargyl pyrene was prepared independently as a photoactive click component. Finally, azido functionalized PVA was coupled to propargyl pyrene with high efficiency by click chemistry. Incorporation of pyrene functionality in the resulting polymer was confirmed by spectral analysis. It is also shown that pyrene functionalized PVA (PVA-Py) exhibited characteristic fluorescence properties and improved solubility in highly polar solvents such as water, DMSO, and DMF as well as less polar solvent such as THF compared with pristine PVA.

Original language	English
Pages (from-to)	1317-1326
Number of pages	10
Journal	Journal of Polymer Science, Part A: Polymer Chemistry
Volume	47
Issue number	5
DOIs	https://doi.org/10.1002/pola.23240
Publication status	Published - 1 Mar 2009

Keywords

"click"
Chemistry
Fluorescence
Functionalization of polymers
Photoreactive effects
Poly(vinyl alcohol)
Polymer modification
Pyrene

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10.1002/pola.23240

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title = "Pyrene functional poly(vinyl alcohol) by {"}click{"} chemistry",

abstract = "Side-chain pyrene functional poly(vinyl alcohol) (PVA) was synthesized by using {"}click chemistry{"} strategy. First, partial tosylation of PVA with p-toluene sulfonyl chloride were performed. The resulting PVA-Ts polymer was then quantitatively converted into poly(vinyl alcohol)-azide (PVA-N 3) in the presence of NaN3/DMF at 60°C. Propargyl pyrene was prepared independently as a photoactive click component. Finally, azido functionalized PVA was coupled to propargyl pyrene with high efficiency by click chemistry. Incorporation of pyrene functionality in the resulting polymer was confirmed by spectral analysis. It is also shown that pyrene functionalized PVA (PVA-Py) exhibited characteristic fluorescence properties and improved solubility in highly polar solvents such as water, DMSO, and DMF as well as less polar solvent such as THF compared with pristine PVA.",

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year = "2009",

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AU - Gacal, Bahadir N.

AU - Koz, Banu

AU - Gacal, Burcin

AU - Kiskan, Baris

AU - Erdogan, Matem

AU - Yagci, Yusuf

PY - 2009/3/1

Y1 - 2009/3/1

N2 - Side-chain pyrene functional poly(vinyl alcohol) (PVA) was synthesized by using "click chemistry" strategy. First, partial tosylation of PVA with p-toluene sulfonyl chloride were performed. The resulting PVA-Ts polymer was then quantitatively converted into poly(vinyl alcohol)-azide (PVA-N 3) in the presence of NaN3/DMF at 60°C. Propargyl pyrene was prepared independently as a photoactive click component. Finally, azido functionalized PVA was coupled to propargyl pyrene with high efficiency by click chemistry. Incorporation of pyrene functionality in the resulting polymer was confirmed by spectral analysis. It is also shown that pyrene functionalized PVA (PVA-Py) exhibited characteristic fluorescence properties and improved solubility in highly polar solvents such as water, DMSO, and DMF as well as less polar solvent such as THF compared with pristine PVA.

AB - Side-chain pyrene functional poly(vinyl alcohol) (PVA) was synthesized by using "click chemistry" strategy. First, partial tosylation of PVA with p-toluene sulfonyl chloride were performed. The resulting PVA-Ts polymer was then quantitatively converted into poly(vinyl alcohol)-azide (PVA-N 3) in the presence of NaN3/DMF at 60°C. Propargyl pyrene was prepared independently as a photoactive click component. Finally, azido functionalized PVA was coupled to propargyl pyrene with high efficiency by click chemistry. Incorporation of pyrene functionality in the resulting polymer was confirmed by spectral analysis. It is also shown that pyrene functionalized PVA (PVA-Py) exhibited characteristic fluorescence properties and improved solubility in highly polar solvents such as water, DMSO, and DMF as well as less polar solvent such as THF compared with pristine PVA.

KW - "click"

KW - Chemistry

KW - Fluorescence

KW - Functionalization of polymers

KW - Photoreactive effects

KW - Poly(vinyl alcohol)

KW - Polymer modification

KW - Pyrene

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JF - Journal of Polymer Science, Part A: Polymer Chemistry

IS - 5

ER -

Pyrene functional poly(vinyl alcohol) by "click" chemistry

Abstract

Keywords

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