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Description:

Incorporating nitrogen into carbon-based materials can significantly modify their electronic properties. A comprehensive understanding of the structural and physical characteristics of aza-polycyclic aromatic hydrocarbons (aza-PAHs) is crucial for developing innovative materials. In this study, four aza-PAHs were synthesized using a combination of the Povarov reaction and intramolecular cyclization reaction via direct C–H arylation. The synthesized compounds were evaluated in terms of the crystal structure, photophysical properties, frontier energy levels, and hole-blocking properties in organic light-emitting diode (OLED). The intramolecular cyclization via direct C–H arylation afforded a condensed azaperylene molecule that exhibited long-wavelength absorption and emission, attributed to the high HOMO level resulting from π-extension.

Rights:

• Creative Commons BY-NC-ND Attribution-NonCommercial-NoDerivs 4.0 International
  

  This is an open access article under the terms of the Creative
  Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.

Keyword: Povarov reaction, Direct C H arylation, OLED, Diazachrysene

Date published: 2025-01-20

Publisher: Wiley

Journal:

• Asian Journal of Organic Chemistry (ISSN: 21935807) vol. 14 issue. 3

Funding:

• JSPS JP23K04884 (科研費)

Manuscript type: Publisher's version (Version of record)

MDR DOI:

First published URL: https://doi.org/10.1002/ajoc.202400625

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Updated at: 2025-03-26 17:26:25 +0900

Published on MDR: 2025-03-26 17:26:26 +0900