Pyrene-cored blue-light emitting [4]helicenes

Synthesis, crystal structures, and photophysical properties

Jian Yong Hu, Arjun Paudel, Nobuyuki Seto, Xing Feng, Masanao Era, Taisuke Matsumoto, Junji Tanaka, Mark R.J. Elsegood, Carl Redshaw, Takehiko Yamato

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The synthesis, crystal structures and photophysical properties of two types of pyrene-cored blue-light emitting [4]helicenes (7 and 9) are reported. The chemical structures of all synthesized compounds were fully confirmed by 1H and 13C NMR spectra, mass spectroscopy as well as elemental analysis. Single-crystal X-ray analysis of these [4]helicenes revealed that there are two types of laterally naphthalene annulated helical architectures, which are clearly influenced by different R substituents. The photophysical properties of the [4]helicenes (7 and 9) were fully investigated in both solutions and films, along with the pre-cyclization products, 4,9- and 4,10-bis(phenylethenyl)pyrenes (6 and 8). Notable optical features were obtained in these compounds, which make them promising candidates for several important applications in modern electronic and optoelectronic devices, such as blue emitters in organic light-emitting devices (OLEDs), or as models for further exploring the development of a new generation of organic materials based on pyrene.

Original languageEnglish
Pages (from-to)2186-2197
Number of pages12
JournalOrganic and Biomolecular Chemistry
Volume11
Issue number13
DOIs
Publication statusPublished - Apr 7 2013

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pyrenes
Crystal structure
Light
crystal structure
Pyrenes
synthesis
Equipment and Supplies
Cyclization
X ray analysis
organic materials
optoelectronic devices
naphthalene
Optoelectronic devices
Mass Spectrometry
emitters
mass spectroscopy
Nuclear magnetic resonance
X-Rays
Single crystals
Spectroscopy

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Pyrene-cored blue-light emitting [4]helicenes : Synthesis, crystal structures, and photophysical properties. / Hu, Jian Yong; Paudel, Arjun; Seto, Nobuyuki; Feng, Xing; Era, Masanao; Matsumoto, Taisuke; Tanaka, Junji; Elsegood, Mark R.J.; Redshaw, Carl; Yamato, Takehiko.

In: Organic and Biomolecular Chemistry, Vol. 11, No. 13, 07.04.2013, p. 2186-2197.

Research output: Contribution to journalArticle

Hu, JY, Paudel, A, Seto, N, Feng, X, Era, M, Matsumoto, T, Tanaka, J, Elsegood, MRJ, Redshaw, C & Yamato, T 2013, 'Pyrene-cored blue-light emitting [4]helicenes: Synthesis, crystal structures, and photophysical properties', Organic and Biomolecular Chemistry, vol. 11, no. 13, pp. 2186-2197. https://doi.org/10.1039/c3ob27320b
Hu, Jian Yong ; Paudel, Arjun ; Seto, Nobuyuki ; Feng, Xing ; Era, Masanao ; Matsumoto, Taisuke ; Tanaka, Junji ; Elsegood, Mark R.J. ; Redshaw, Carl ; Yamato, Takehiko. / Pyrene-cored blue-light emitting [4]helicenes : Synthesis, crystal structures, and photophysical properties. In: Organic and Biomolecular Chemistry. 2013 ; Vol. 11, No. 13. pp. 2186-2197.
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