Issue 13, 2013

Pyrene-cored blue-light emitting [4]helicenes: synthesis, crystal structures, and photophysical properties

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.

Graphical abstract: Pyrene-cored blue-light emitting [4]helicenes: synthesis, crystal structures, and photophysical properties

Supplementary files

Article information

Article type
Paper
Submitted
29 Nov 2012
Accepted
23 Jan 2013
First published
23 Jan 2013

Org. Biomol. Chem., 2013,11, 2186-2197

Pyrene-cored blue-light emitting [4]helicenes: synthesis, crystal structures, and photophysical properties

J. Hu, A. Paudel, N. Seto, X. Feng, M. Era, T. Matsumoto, J. Tanaka, M. R. J. Elsegood, C. Redshaw and T. Yamato, Org. Biomol. Chem., 2013, 11, 2186 DOI: 10.1039/C3OB27320B

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