ChemSel2016.pdf (1.2 MB)
Extended [pi]-conjugated pyrene derivatives: structural, photophysical and electrochemical properties
journal contribution
posted on 2016-12-08, 12:14 authored by Xing Feng, Nobuyuki Seto, Chuan-Zeng Wang, Taisuke Matsumoto, Junji Tanaka, Xian-Fu Wei, Mark ElsegoodMark Elsegood, Lynne Horsburgh, Carl Redshaw, Takehiko YamatoThis article presents a set of extended [pi]-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 [pi]-[pi] 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.
Funding
This work was performed under the Cooperative Research Program of “Network Joint Research Center for Materials and Devices (Institute for Materials Chemistry and Engineering, Kyushu University)”. We also would like to thank the EPSRC (overseas travel grant to C.R.), The Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry and The Scientific Research Common Program of Beijing Municipal Commission of Education for financial support (18190115/008).
History
School
- Science
Department
- Chemistry
Published in
ChemistrySelectVolume
1Issue
9Pages
1926 - 1932Citation
FENG, X. ... et al, 2016. Extended [pi]-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1 (9), pp. 1926-1932.Publisher
© WileyVersion
- AM (Accepted Manuscript)
Publisher statement
This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/Acceptance date
2016-05-25Publication date
2016Notes
This is the peer reviewed version of the following article: FENG, X. ... et al, 2016. Extended [pi]-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1 (9), pp. 1926-1932., 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.ISSN
2365-6549Publisher version
Language
- en