- Regioselective Substitution at the 1,3- and 6,8-Positions of Pyrene for the Construction of Small Dipolar Molecules
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This article presents a novel asymmetrical functionalization strategy for the construction of dipolar molecules via efficient regioselective functionalization along the Z-axis of pyrene at both the 1,3- and 6,8-positions. Three asymmetrically substituted
- Feng, Xing,Tomiyasu, Hirotsugu,Hu, Jian-Yong,Wei, Xianfu,Redshaw, Carl,Elsegood, Mark R.J.,Horsburgh, Lynne,Teat, Simon J.,Yamato, Takehiko
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- A [...] derivative and its preparation method and application
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The invention relates to the field of organic electroluminescent materials, and in particular relates to a pyrene derivative as well as a preparation method and application thereof; the pyrene derivative provided by the invention is that large substituent group units having different electronic properties and rigid structures are introduced at the positions of 1-, 3-, 6- and 8- of pyrene; intermolecular phi-phi stacking can be inhibited through molecular coplanar damage; therefore, an exciplex is difficult to form; the crystallization process is inhibited; the film-forming property is improved; therefore, the purpose of improving device properties is achieved; because an electron donor and an electron acceptor are introduced at special positions, a pyrene ring is asymmetrically functionalized; push-pull type molecular is constructed; intramolecular charge transfer is induced to generate; the charge transmission capability of the material is increased; and an organic light-emitting material having blue light property and high fluorescence quantum yield can be prepared. Compared with the existing light-emitting material, the light-emitting efficiency, the colour purity and the stability of the material are greatly improved.
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- Pyrene-based Y-shaped solid-state blue emitters: Synthesis, characterization, and photoluminescence
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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
- Feng, Xing,Hu, Jian-Yong,Yi, Liu,Seto, Nobuyuki,Tao, Zhu,Redshaw, Carl,Elsegood, Mark R. J.,Yamato, Takehiko
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p. 2854 - 2863
(2013/02/23)
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