Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures

Ichiro Takemura, Keita Katayose, Hiroyuki Nishide

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

Thiaheterohelicenes were often characterized by unique optical activity and stable doped state due to their π-electron-excess conjugation on the thiophene ring. However there have been no reports of the thiaheterohelicene with a high molecular weight or a sufficient number of repeating units to form a helical structure. This paper described the electronic state and helicity-control of the polythiaheterohelicenes. The alkylsulfmyl-substituted poly(1,3-phenylene)s were synthesized. Red shift of the π-π transition absorption indicated that the ring-closing structure caused the extension of the π-conjugation. The MCD signal at the long-wavelength was assigned to the degeneration of the p-orbitals. A helical conformation was induced to one side in good and poor solvent mixtures, and the following ring-closing reaction afforded the same helical structure which was firmed by strong covalent bonds. The helical structure was very stiff as evidence by the independencies in the CD spectra of temperature and solvent species. The helical polymer with long alkyl chain exhibited a partially oriented structure in the polarized microscopy.

Original languageEnglish
Title of host publicationPolymer Preprints, Japan
Pages2875-2876
Number of pages2
Volume54
Edition2
Publication statusPublished - 2005
Event54th SPSJ Symposium on Macromolecules - Yamagata
Duration: 2005 Sep 202005 Sep 22

Other

Other54th SPSJ Symposium on Macromolecules
CityYamagata
Period05/9/2005/9/22

Fingerprint

Covalent bonds
Electronic states
Thiophene
Conformations
Microscopic examination
Molecular weight
Wavelength
Electrons
Polymers
Temperature

Keywords

  • Helical polymer
  • Helicene
  • MCD
  • Ring closing
  • Sulfonium salt

ASJC Scopus subject areas

  • Engineering(all)

Cite this

Takemura, I., Katayose, K., & Nishide, H. (2005). Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures. In Polymer Preprints, Japan (2 ed., Vol. 54, pp. 2875-2876)

Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures. / Takemura, Ichiro; Katayose, Keita; Nishide, Hiroyuki.

Polymer Preprints, Japan. Vol. 54 2. ed. 2005. p. 2875-2876.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Takemura, I, Katayose, K & Nishide, H 2005, Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures. in Polymer Preprints, Japan. 2 edn, vol. 54, pp. 2875-2876, 54th SPSJ Symposium on Macromolecules, Yamagata, 05/9/20.
Takemura I, Katayose K, Nishide H. Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures. In Polymer Preprints, Japan. 2 ed. Vol. 54. 2005. p. 2875-2876
Takemura, Ichiro ; Katayose, Keita ; Nishide, Hiroyuki. / Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures. Polymer Preprints, Japan. Vol. 54 2. ed. 2005. pp. 2875-2876
@inproceedings{30a2e8bc91014070815173e02fe23ab3,
title = "Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures",
abstract = "Thiaheterohelicenes were often characterized by unique optical activity and stable doped state due to their π-electron-excess conjugation on the thiophene ring. However there have been no reports of the thiaheterohelicene with a high molecular weight or a sufficient number of repeating units to form a helical structure. This paper described the electronic state and helicity-control of the polythiaheterohelicenes. The alkylsulfmyl-substituted poly(1,3-phenylene)s were synthesized. Red shift of the π-π transition absorption indicated that the ring-closing structure caused the extension of the π-conjugation. The MCD signal at the long-wavelength was assigned to the degeneration of the p-orbitals. A helical conformation was induced to one side in good and poor solvent mixtures, and the following ring-closing reaction afforded the same helical structure which was firmed by strong covalent bonds. The helical structure was very stiff as evidence by the independencies in the CD spectra of temperature and solvent species. The helical polymer with long alkyl chain exhibited a partially oriented structure in the polarized microscopy.",
keywords = "Helical polymer, Helicene, MCD, Ring closing, Sulfonium salt",
author = "Ichiro Takemura and Keita Katayose and Hiroyuki Nishide",
year = "2005",
language = "English",
volume = "54",
pages = "2875--2876",
booktitle = "Polymer Preprints, Japan",
edition = "2",

}

TY - GEN

T1 - Synthesis of poly(thiaheterohelicene)s and their conjugated helical structures

AU - Takemura, Ichiro

AU - Katayose, Keita

AU - Nishide, Hiroyuki

PY - 2005

Y1 - 2005

N2 - Thiaheterohelicenes were often characterized by unique optical activity and stable doped state due to their π-electron-excess conjugation on the thiophene ring. However there have been no reports of the thiaheterohelicene with a high molecular weight or a sufficient number of repeating units to form a helical structure. This paper described the electronic state and helicity-control of the polythiaheterohelicenes. The alkylsulfmyl-substituted poly(1,3-phenylene)s were synthesized. Red shift of the π-π transition absorption indicated that the ring-closing structure caused the extension of the π-conjugation. The MCD signal at the long-wavelength was assigned to the degeneration of the p-orbitals. A helical conformation was induced to one side in good and poor solvent mixtures, and the following ring-closing reaction afforded the same helical structure which was firmed by strong covalent bonds. The helical structure was very stiff as evidence by the independencies in the CD spectra of temperature and solvent species. The helical polymer with long alkyl chain exhibited a partially oriented structure in the polarized microscopy.

AB - Thiaheterohelicenes were often characterized by unique optical activity and stable doped state due to their π-electron-excess conjugation on the thiophene ring. However there have been no reports of the thiaheterohelicene with a high molecular weight or a sufficient number of repeating units to form a helical structure. This paper described the electronic state and helicity-control of the polythiaheterohelicenes. The alkylsulfmyl-substituted poly(1,3-phenylene)s were synthesized. Red shift of the π-π transition absorption indicated that the ring-closing structure caused the extension of the π-conjugation. The MCD signal at the long-wavelength was assigned to the degeneration of the p-orbitals. A helical conformation was induced to one side in good and poor solvent mixtures, and the following ring-closing reaction afforded the same helical structure which was firmed by strong covalent bonds. The helical structure was very stiff as evidence by the independencies in the CD spectra of temperature and solvent species. The helical polymer with long alkyl chain exhibited a partially oriented structure in the polarized microscopy.

KW - Helical polymer

KW - Helicene

KW - MCD

KW - Ring closing

KW - Sulfonium salt

UR - http://www.scopus.com/inward/record.url?scp=33645578181&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33645578181&partnerID=8YFLogxK

M3 - Conference contribution

VL - 54

SP - 2875

EP - 2876

BT - Polymer Preprints, Japan

ER -