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

doi:10.1039/C3OB27320B

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

Jian-Yong Hu,*^ab Arjun Paudel,^a Nobuyuki Seto,^a Xing Feng,^a Masanao Era,^a Taisuke Matsumoto,^c Junji Tanaka,^c Mark R. J. Elsegood,^d Carl Redshaw^e and Takehiko Yamato*^a

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^a Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo machi 1, Saga-shi, Saga, Japan
E-mail: yamatot@cc.saga-u.ac.jp
Fax: +81-952-288548

^b Department of Organic Device Engineering, Yamagata University, Yonezawa, Yamagata, Japan
E-mail: hujianyong@yz.yamagata-u.ac.jp
Fax: +81-238-263412

^c Institute of Material Chemistry and Engineering, Kyushu University, 6-1, Kasugakoen, Kasuga 816-8580, Japan

^d Chemistry Department, Loughborough, University, Loughborough, Leicestershire, UK

^e Department of Chemistry, The University of Hull, Hull, HU6 7RX, UK

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.

Organic & Biomolecular Chemistry

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

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

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