New alternative donor-acceptor arranged poly(aryleneethynylene)s and their related compounds composed of five-membered electron-accepting 1,3,4-thiadiazole, 1,2,4-triazole, or 3,4-dinitrothiophene units: Synthesis, packing structure, and optical properties

Takuma Yasuda, Tatsuya Imase, Yoshiyuki Nakamura, Takakazu Yamamoto

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Abstract

A series of new poly(aryleneethynylene)-type π-conjugated copolymers, which consist of an electron-accepting 1,3,4-thiadiazole, 4-alkyl-1,2,4- triazole, or 3,4-dinitrothiophene unit and an electrondonating 1,4-didodecyloxybenzene or N-dodecylpyrrole unit, were prepared in 81-93% yields by palladium-catalyzed polycondensation. Their related model compounds (PhC≡C-Ar-C≡CPh; Ar = the electron-accepting unit) were also synthesized. GPC traces of the polymers gave number average molecular weights (Mn's) of 6900-29 700. The polymers formed a molecular assembly and a birefringent phase as revealed by powder X-ray diffraction (XRD) analysis and polarized light optical microscopy (POM). They formed an aligned structure on a platinum plate. The UV-vis peaks of the polymers appeared in the range of 385-522 nm in solutions, and the peak was shifted by 10-44 nm to a longer wavelength in films, according to intermolecular electronic interaction. The density functional theory (DFT) calculations supported the presence of strong intermolecular interaction between the polymer molecules. The polymers composed of a 1,3,4-thiadiazole or a 1,2,4-triazole unit exhibited photoluminescence with quantum yields of about 50% in chloroform. The polymers were electrochemically active and showed the reduction peak in a range of -1.1 through -2.2 V vs Ag+/Ag.

Original languageEnglish
Pages (from-to)4687-4697
Number of pages11
JournalMacromolecules
Volume38
Issue number11
DOIs
Publication statusPublished - May 31 2005
Externally publishedYes

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Polymers
Optical properties
Electrons
Optical microscopy
Palladium
Quantum yield
Light polarization
Polycondensation
Chloroform
Chlorine compounds
Platinum
X ray diffraction analysis
Density functional theory
1,2,4-triazole
1,3,4-thiadiazole
Photoluminescence
Copolymers
Molecular weight
Powders
Wavelength

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "New alternative donor-acceptor arranged poly(aryleneethynylene)s and their related compounds composed of five-membered electron-accepting 1,3,4-thiadiazole, 1,2,4-triazole, or 3,4-dinitrothiophene units: Synthesis, packing structure, and optical properties",
abstract = "A series of new poly(aryleneethynylene)-type π-conjugated copolymers, which consist of an electron-accepting 1,3,4-thiadiazole, 4-alkyl-1,2,4- triazole, or 3,4-dinitrothiophene unit and an electrondonating 1,4-didodecyloxybenzene or N-dodecylpyrrole unit, were prepared in 81-93{\%} yields by palladium-catalyzed polycondensation. Their related model compounds (PhC≡C-Ar-C≡CPh; Ar = the electron-accepting unit) were also synthesized. GPC traces of the polymers gave number average molecular weights (Mn's) of 6900-29 700. The polymers formed a molecular assembly and a birefringent phase as revealed by powder X-ray diffraction (XRD) analysis and polarized light optical microscopy (POM). They formed an aligned structure on a platinum plate. The UV-vis peaks of the polymers appeared in the range of 385-522 nm in solutions, and the peak was shifted by 10-44 nm to a longer wavelength in films, according to intermolecular electronic interaction. The density functional theory (DFT) calculations supported the presence of strong intermolecular interaction between the polymer molecules. The polymers composed of a 1,3,4-thiadiazole or a 1,2,4-triazole unit exhibited photoluminescence with quantum yields of about 50{\%} in chloroform. The polymers were electrochemically active and showed the reduction peak in a range of -1.1 through -2.2 V vs Ag+/Ag.",
author = "Takuma Yasuda and Tatsuya Imase and Yoshiyuki Nakamura and Takakazu Yamamoto",
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T1 - New alternative donor-acceptor arranged poly(aryleneethynylene)s and their related compounds composed of five-membered electron-accepting 1,3,4-thiadiazole, 1,2,4-triazole, or 3,4-dinitrothiophene units

T2 - Synthesis, packing structure, and optical properties

AU - Yasuda, Takuma

AU - Imase, Tatsuya

AU - Nakamura, Yoshiyuki

AU - Yamamoto, Takakazu

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Y1 - 2005/5/31

N2 - A series of new poly(aryleneethynylene)-type π-conjugated copolymers, which consist of an electron-accepting 1,3,4-thiadiazole, 4-alkyl-1,2,4- triazole, or 3,4-dinitrothiophene unit and an electrondonating 1,4-didodecyloxybenzene or N-dodecylpyrrole unit, were prepared in 81-93% yields by palladium-catalyzed polycondensation. Their related model compounds (PhC≡C-Ar-C≡CPh; Ar = the electron-accepting unit) were also synthesized. GPC traces of the polymers gave number average molecular weights (Mn's) of 6900-29 700. The polymers formed a molecular assembly and a birefringent phase as revealed by powder X-ray diffraction (XRD) analysis and polarized light optical microscopy (POM). They formed an aligned structure on a platinum plate. The UV-vis peaks of the polymers appeared in the range of 385-522 nm in solutions, and the peak was shifted by 10-44 nm to a longer wavelength in films, according to intermolecular electronic interaction. The density functional theory (DFT) calculations supported the presence of strong intermolecular interaction between the polymer molecules. The polymers composed of a 1,3,4-thiadiazole or a 1,2,4-triazole unit exhibited photoluminescence with quantum yields of about 50% in chloroform. The polymers were electrochemically active and showed the reduction peak in a range of -1.1 through -2.2 V vs Ag+/Ag.

AB - A series of new poly(aryleneethynylene)-type π-conjugated copolymers, which consist of an electron-accepting 1,3,4-thiadiazole, 4-alkyl-1,2,4- triazole, or 3,4-dinitrothiophene unit and an electrondonating 1,4-didodecyloxybenzene or N-dodecylpyrrole unit, were prepared in 81-93% yields by palladium-catalyzed polycondensation. Their related model compounds (PhC≡C-Ar-C≡CPh; Ar = the electron-accepting unit) were also synthesized. GPC traces of the polymers gave number average molecular weights (Mn's) of 6900-29 700. The polymers formed a molecular assembly and a birefringent phase as revealed by powder X-ray diffraction (XRD) analysis and polarized light optical microscopy (POM). They formed an aligned structure on a platinum plate. The UV-vis peaks of the polymers appeared in the range of 385-522 nm in solutions, and the peak was shifted by 10-44 nm to a longer wavelength in films, according to intermolecular electronic interaction. The density functional theory (DFT) calculations supported the presence of strong intermolecular interaction between the polymer molecules. The polymers composed of a 1,3,4-thiadiazole or a 1,2,4-triazole unit exhibited photoluminescence with quantum yields of about 50% in chloroform. The polymers were electrochemically active and showed the reduction peak in a range of -1.1 through -2.2 V vs Ag+/Ag.

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