Xing Feng
Pyrene-based Y-shaped solid-state blue emitters: Synthesis, characterization, and photoluminescence
Feng, Xing; Hu, Jian Yong; Yi, Liu; Seto, Nobuyuki; Tao, Zhu; Redshaw, Carl; Elsegood, Mark R.J.; Yamato, Takehiko
Authors
Jian Yong Hu
Liu Yi
Nobuyuki Seto
Zhu Tao
Emeritus Professor Carl Redshaw C.Redshaw@hull.ac.uk
Emeritus Professor
Mark R.J. Elsegood
Takehiko Yamato
Abstract
A series of pyrene-based Y-shaped blue emitters, namely, 7-tert-butyl-1,3-diarylpyrenes 4 were synthesized by the Suzuki cross-coupling reaction of 7-tert-butyl-1,3-dibromopyrene with a variety of p-substituted phenylboronic acids in good to excellent yields. These compounds were fully characterized by X-ray crystallography, UV/Vis absorption and fluorescence spectroscopy, DFT calculations, thermogravimetric analysis, and differential scanning calorimetry. Single-crystal X-ray analysis revealed that the Y-shaped arylpyrenes exhibited a low degree of π stacking owing to the steric effect of the bulky tert-butyl group in the pyrene ring at the 7-position, and thus, the intermolecular π-π interactions were effectively suppressed in the solid state. Despite the significantly twisted nonplanar structures, these molecules still displayed efficient intramolecular charge-transfer emissions with clear solvatochromic shifts on increasing solvent polarity. An intriguing fact is that all of these molecules show highly blue emissions with excellent quantum yields in the solid state. Additionally, the two compounds containing the strongest electron-accepting groups, CN (4 d) and CHO (4 f), possess high thermal stability, which, together with their excellent solid-state fluorescence efficiency, makes them promising potential blue emitters in organic light-emitting device applications. Shades of blue: Pyrene-based Y-shaped blue solid-state emitters, 7-tert-butyl-1,3-diarylpyrenes 1, were synthesized by Suzuki cross-coupling reactions in good to excellent yields. Studies on single-crystal X-ray structures and the photophysical properties of these compounds strongly suggest that they are promising blue emitters in organic light-emitting device applications. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Citation
Feng, X., Hu, J. Y., Yi, L., Seto, N., Tao, Z., Redshaw, C., Elsegood, M. R., & Yamato, T. (2012). Pyrene-based Y-shaped solid-state blue emitters: Synthesis, characterization, and photoluminescence. Chemistry - An Asian Journal, 7(12), 2854-2863. https://doi.org/10.1002/asia.201200530
Journal Article Type | Article |
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Publication Date | Dec 1, 2012 |
Deposit Date | Jun 8, 2022 |
Journal | Chemistry - An Asian Journal |
Print ISSN | 1861-4728 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 7 |
Issue | 12 |
Pages | 2854-2863 |
DOI | https://doi.org/10.1002/asia.201200530 |
Public URL | https://hull-repository.worktribe.com/output/3622150 |