A new and simple polycondensation method for the synthesis of sulfur-linked isoindole-phenylene based blue light-emitting copolymers

Miklós Nagy, Dávid Rácz, P. Herczegh, G. Batta, G. Deák, Balázs Lukács, I. Jóna, M. Zsuga, S. Kéki

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

New isoindole containing blue light-emitting copolymers, poly[(1,2-isoindolene)-(1-sulfane-4-phenylene)] and poly[(1,2-isoindolene)-(1- sulfane-3-phenylene)] were prepared by a simple polycondensation method between ortho-phthalaldehyde and para-, or meta-aminothiophenol. The reaction proceeds under mild conditions, giving pure copolymers with high yields and does not require a catalyst. The formation of both linear and cyclic products was observed. The polymerization is largely solvent dependent and the maximum obtainable molecular weight is limited by the solubility of the copolymers. Detailed NMR study revealed orthogonal sigma-pi interactions between the chain segments of the 1,4-copolymer. The optical properties were also studied and it was found that both copolymers emitted blue light in solution with relatively narrow emission band. Unlike their simple isoindole derivatives, the copolymers proved to be stable for several weeks and can serve as model compounds for the synthesis of new and versatile isoindole-containing light-emitting polymers.

Original languageEnglish
Pages (from-to)549-557
Number of pages9
JournalEuropean Polymer Journal
Volume49
Issue number2
DOIs
Publication statusPublished - Feb 2013

Fingerprint

Isoindoles
Polycondensation
Sulfur
copolymers
sulfur
Copolymers
synthesis
o-Phthalaldehyde
molecular weight
Polymers
solubility
polymerization
Optical properties
Solubility
Molecular weight
Polymerization
Nuclear magnetic resonance
Derivatives
optical properties
catalysts

Keywords

  • Conjugated polymers
  • Copolymer
  • Isoindole
  • Light-emitting polymer
  • Polycondensation

ASJC Scopus subject areas

  • Polymers and Plastics
  • Physics and Astronomy(all)
  • Organic Chemistry

Cite this

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title = "A new and simple polycondensation method for the synthesis of sulfur-linked isoindole-phenylene based blue light-emitting copolymers",
abstract = "New isoindole containing blue light-emitting copolymers, poly[(1,2-isoindolene)-(1-sulfane-4-phenylene)] and poly[(1,2-isoindolene)-(1- sulfane-3-phenylene)] were prepared by a simple polycondensation method between ortho-phthalaldehyde and para-, or meta-aminothiophenol. The reaction proceeds under mild conditions, giving pure copolymers with high yields and does not require a catalyst. The formation of both linear and cyclic products was observed. The polymerization is largely solvent dependent and the maximum obtainable molecular weight is limited by the solubility of the copolymers. Detailed NMR study revealed orthogonal sigma-pi interactions between the chain segments of the 1,4-copolymer. The optical properties were also studied and it was found that both copolymers emitted blue light in solution with relatively narrow emission band. Unlike their simple isoindole derivatives, the copolymers proved to be stable for several weeks and can serve as model compounds for the synthesis of new and versatile isoindole-containing light-emitting polymers.",
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author = "Mikl{\'o}s Nagy and D{\'a}vid R{\'a}cz and P. Herczegh and G. Batta and G. De{\'a}k and Bal{\'a}zs Luk{\'a}cs and I. J{\'o}na and M. Zsuga and S. K{\'e}ki",
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T1 - A new and simple polycondensation method for the synthesis of sulfur-linked isoindole-phenylene based blue light-emitting copolymers

AU - Nagy, Miklós

AU - Rácz, Dávid

AU - Herczegh, P.

AU - Batta, G.

AU - Deák, G.

AU - Lukács, Balázs

AU - Jóna, I.

AU - Zsuga, M.

AU - Kéki, S.

PY - 2013/2

Y1 - 2013/2

N2 - New isoindole containing blue light-emitting copolymers, poly[(1,2-isoindolene)-(1-sulfane-4-phenylene)] and poly[(1,2-isoindolene)-(1- sulfane-3-phenylene)] were prepared by a simple polycondensation method between ortho-phthalaldehyde and para-, or meta-aminothiophenol. The reaction proceeds under mild conditions, giving pure copolymers with high yields and does not require a catalyst. The formation of both linear and cyclic products was observed. The polymerization is largely solvent dependent and the maximum obtainable molecular weight is limited by the solubility of the copolymers. Detailed NMR study revealed orthogonal sigma-pi interactions between the chain segments of the 1,4-copolymer. The optical properties were also studied and it was found that both copolymers emitted blue light in solution with relatively narrow emission band. Unlike their simple isoindole derivatives, the copolymers proved to be stable for several weeks and can serve as model compounds for the synthesis of new and versatile isoindole-containing light-emitting polymers.

AB - New isoindole containing blue light-emitting copolymers, poly[(1,2-isoindolene)-(1-sulfane-4-phenylene)] and poly[(1,2-isoindolene)-(1- sulfane-3-phenylene)] were prepared by a simple polycondensation method between ortho-phthalaldehyde and para-, or meta-aminothiophenol. The reaction proceeds under mild conditions, giving pure copolymers with high yields and does not require a catalyst. The formation of both linear and cyclic products was observed. The polymerization is largely solvent dependent and the maximum obtainable molecular weight is limited by the solubility of the copolymers. Detailed NMR study revealed orthogonal sigma-pi interactions between the chain segments of the 1,4-copolymer. The optical properties were also studied and it was found that both copolymers emitted blue light in solution with relatively narrow emission band. Unlike their simple isoindole derivatives, the copolymers proved to be stable for several weeks and can serve as model compounds for the synthesis of new and versatile isoindole-containing light-emitting polymers.

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KW - Light-emitting polymer

KW - Polycondensation

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