Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties

Feng, Xing; Seto, Nobuyuki; Wang, Chuan-Zeng; Matsumoto, Taisuke; Tanaka, Junji; Wei, Xian-Fu; Elsegood, Mark R.J.; Horsburgh, Lynne; Redshaw, Carl; Yamato, Takehiko

Abstract

This article presents a set of extended π-conjugated pyrene derivatives, namely 1,3-di(arylethynyl)-7-tert-butylpyrenes, which were synthesized by a Pd-catalyzed Sonogashira coupling reaction of 1,3-dibromo-7-tert-butylpyrenes with the corresponding arylethynyl group in good yields. Despite the presence of the tert-butyl group located at the 7-position of pyrene, X-ray crystallographic analyses show that the planarity of the Y-shaped molecules still exhibits strong face-to-face π-π stacking in the solid state; all of the compounds exhibit blue or green emission with high quantum yields (QYs) in dichloromethane. DFT calculations and electrochemistry revealed that this category of compound possesses hole-transporting characteristics. In addition, with strong electron-donating (-N(CH₃)₂) or electron-withdrawing (-CHO) groups in 2 d or 2 f, these molecules displayed efficient intramolecular charge-transfer (ICT) emissions with solvatochromic shifts from blue to yellow (green) on increasing the solvent polarity. Furthermore, the compounds 2 d and 2 f possess strong CT characteristics.

Citation

Feng, X., Seto, N., Wang, C.-Z., Matsumoto, T., Tanaka, J., Wei, X.-F., Elsegood, M. R., Horsburgh, L., Redshaw, C., & Yamato, T. (2016). Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1(9), 1926-1932. https://doi.org/10.1002/slct.201600598

• Journal Article Type: Article
• Acceptance Date: May 25, 2016
• Online Publication Date: Jun 21, 2016
• Publication Date: Jun 16, 2016
• Deposit Date: Nov 17, 2016
• Publicly Available Date: Nov 17, 2016
• Journal: ChemistrySelect
• Electronic ISSN: 2365-6549
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 1
• Issue: 9
• Pages: 1926-1932
• DOI: https://doi.org/10.1002/slct.201600598
• Keywords: Pyrenes
• Public URL: https://hull-repository.worktribe.com/output/445352
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/slct.201600598/abstract;jsessionid=A65A3B19362925C2974E3D69883F7CD9.f04t01
• Additional Information: This is the peer reviewed version of the following article: X. Feng , N. Seto, C.-Z. Wang, T. Matsumoto, J. Tanaka, X.-F. Wei, M. R. J. Elsegood, L. Horsburgh, C. Redshaw, T. Yamato, ChemistrySelect 2016, 1, 1926, which has been published in final form at http://dx.doi.org/10.1002/slct.201600598 . This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
• Contract Date: Nov 17, 2016