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

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. © The Royal Society of Chemistry 2013.

Citation

Hu, J. Y., Paudel, A., Seto, N., Feng, X., Era, M., Matsumoto, T., Tanaka, J., Elsegood, M. R., Redshaw, C., & Yamato, T. (2013). Pyrene-cored blue-light emitting [4]helicenes: Synthesis, crystal structures, and photophysical properties. Organic & biomolecular chemistry, 11(13), 2186-2197. https://doi.org/10.1039/c3ob27320b

• Journal Article Type: Article
• Acceptance Date: Jan 23, 2013
• Online Publication Date: Jan 23, 2013
• Publication Date: Apr 7, 2013
• Deposit Date: Jun 8, 2022
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 11
• Issue: 13
• Pages: 2186-2197
• DOI: https://doi.org/10.1039/c3ob27320b
• Public URL: https://hull-repository.worktribe.com/output/3622031