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Pyrene‐fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies

Pyrene‐fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and... Molecular packing and microstructure can play a crucial role in the photophysical and electronic properties of organic semiconductor materials. This article presents six pyrene‐fused dibenzoazatetracenes 3 and the relationship between their molecular structures and the emission, and as well as the morphology has been investigated. All of the compounds display an aggregation‐caused emission quenching effect due to the extended π‐conjugation associated with the close π‐π stacking in their crystal structures. In terms of fluorescence, the compounds emitted sky‐blue emission with a maximum peak (λmaxem) in the range 469–474 nm with a quantum yield (Φf) of 0.37–0.50 in solution. In the solid state, the emission maximum red‐shifts to ∼528 nm and possesses a relatively low quantum yield (<0.16). In addition, the electronic effects of the terminal group shows only a limited effect on the emission behavior. On the other hand, tert‐butyl groups have been introduced at the pyrene core, and contribute to enhance the solubility of the compound, and also improve the quality of the morphology. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Pyrene‐fused Dibenzoazatetracenes: Synthesis, Crystal Structures, Photophysical Properties and their Morphologies

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References (41)

Publisher
Wiley
Copyright
© 2021 Wiley‐VCH GmbH
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.202000616
Publisher site
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Abstract

Molecular packing and microstructure can play a crucial role in the photophysical and electronic properties of organic semiconductor materials. This article presents six pyrene‐fused dibenzoazatetracenes 3 and the relationship between their molecular structures and the emission, and as well as the morphology has been investigated. All of the compounds display an aggregation‐caused emission quenching effect due to the extended π‐conjugation associated with the close π‐π stacking in their crystal structures. In terms of fluorescence, the compounds emitted sky‐blue emission with a maximum peak (λmaxem) in the range 469–474 nm with a quantum yield (Φf) of 0.37–0.50 in solution. In the solid state, the emission maximum red‐shifts to ∼528 nm and possesses a relatively low quantum yield (<0.16). In addition, the electronic effects of the terminal group shows only a limited effect on the emission behavior. On the other hand, tert‐butyl groups have been introduced at the pyrene core, and contribute to enhance the solubility of the compound, and also improve the quality of the morphology.

Journal

Asian Journal of Organic Chemistry – Wiley

Published: Jan 1, 2021

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