Facile route to organoboron quinolate polymers through boron-induced ether cleavage

Haiyan Li, Frieder Jäkle

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Two new organoboron quinolate polymers were prepared under exceptionally mild conditions via a novel polycondensation reaction involving boron-induced ether cleavage. The polymers, which contain both the boron and quinolato moieties in the main chain, were characterized by multinuclear and 2D NMR, gel permeation chromatography, and matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. They are readily soluble in common organic solvents and thermally stable to <300 °C according to thermogravimetric analysis. The photophysical properties strongly depend on the nature of the conjugated bridge connecting the organoboron quinolato groups. Therefore, with a highly delocalized Th-C 6H 4-Th (Th = thiophene) linker, the lowest energy absorption corresponds to intramolecular charge transfer (ICT) from this conjugated linker to the pyridyl moiety. In contrast, with a less delocalized biphenyl linker, ICT occurs from the fluorene moiety of the diboron monomer to the pyridyl rings on the basis of time-dependent density functional theory (TD-DFT) calculations on molecular model systems. The polymer with the biphenyl linker displays a strong yellow-green emission, whereas the Th-C 6H 4-Th linker shows an unusual concentration-dependent dual emission as a result of excimer formation.

Original languageEnglish (US)
Pages (from-to)3448-3453
Number of pages6
JournalMacromolecules
Volume42
Issue number10
DOIs
StatePublished - May 26 2009

Fingerprint

Boron
Ether
Ethers
Polymers
Charge transfer
Thiophenes
Energy absorption
Gel permeation chromatography
Thiophene
Polycondensation
Organic solvents
Ionization
Density functional theory
Mass spectrometry
Thermogravimetric analysis
Desorption
Monomers
Nuclear magnetic resonance
Lasers
diphenyl

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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abstract = "Two new organoboron quinolate polymers were prepared under exceptionally mild conditions via a novel polycondensation reaction involving boron-induced ether cleavage. The polymers, which contain both the boron and quinolato moieties in the main chain, were characterized by multinuclear and 2D NMR, gel permeation chromatography, and matrix-assisted laser desorption ionization time-of-flight (MALDI-TOF) mass spectrometry. They are readily soluble in common organic solvents and thermally stable to <300 °C according to thermogravimetric analysis. The photophysical properties strongly depend on the nature of the conjugated bridge connecting the organoboron quinolato groups. Therefore, with a highly delocalized Th-C 6H 4-Th (Th = thiophene) linker, the lowest energy absorption corresponds to intramolecular charge transfer (ICT) from this conjugated linker to the pyridyl moiety. In contrast, with a less delocalized biphenyl linker, ICT occurs from the fluorene moiety of the diboron monomer to the pyridyl rings on the basis of time-dependent density functional theory (TD-DFT) calculations on molecular model systems. The polymer with the biphenyl linker displays a strong yellow-green emission, whereas the Th-C 6H 4-Th linker shows an unusual concentration-dependent dual emission as a result of excimer formation.",
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Facile route to organoboron quinolate polymers through boron-induced ether cleavage. / Li, Haiyan; Jäkle, Frieder.

In: Macromolecules, Vol. 42, No. 10, 26.05.2009, p. 3448-3453.

Research output: Contribution to journalArticle

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