2024-03-29T11:50:05Z
https://nagoya.repo.nii.ac.jp/oai
oai:nagoya.repo.nii.ac.jp:02002693
2023-02-07T00:57:12Z
320:321:322
Indeno[1,2,3,4-pqra]Perylene : A Medium-Sized Aromatic Hydrocarbon Exhibiting Full-Range Visible-Light Absorption
Kato, Masaki
Fukui, Norihito
Shinokubo, Hiroshi
open access
"This is the peer reviewed version of the following article: [M. Kato, N. Fukui, H. Shinokubo, Chem. Eur. J. 2022, 28, e202103647.], which has been published in final form at [https://doi.org/10.1002/chem.202103647]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited."
We report the synthesis and properties of indeno[1,2,3,4-pqra]perylene, which was prepared by the fusion of one anthracene unit with one naphthalene unit via three carbon-carbon bonds. The synthetic route through two-fold C−H arylation enabled not only the synthesis of unsubstituted indenoperylene, but also rapid access to its arylated derivatives on the gram scale. Indenoperylene is a medium-sized aromatic hydrocarbon with the composition C24H12 that is isomeric to coronene. Nevertheless, its absorption covers the entire visible region owing to its small HOMO-LUMO gap. Furthermore, indenoperylene exhibits high stability despite the absence of peripheral substituents. We propose that the unique electronic structure of indenoperylene originates from the coexistence of an electron-withdrawing subunit (benzoaceanthrylene) and an electron-donating subunit (perylene). The electronic properties of indenoperylene were modulated via post-functionalization through regioselective bromination. The current research demonstrates that indenoperylene is a promising candidate as a main skeleton for near-infrared-responsive and redox-active materials.
Wiley
2023-01-10
2022-01-10
eng
journal article
AM
http://hdl.handle.net/2237/0002002693
https://nagoya.repo.nii.ac.jp/records/2002693
https://doi.org/10.1002/chem.202103647
1521-3765
Chemistry - A European Journal
28
2
e202103647
https://nagoya.repo.nii.ac.jp/record/2002693/files/indenoperylene_MS_rev3.pdf
application/pdf
2.1 MB
2023-01-10