In Silico Screening and Experimental Verification of Near‐Infrared‐Emissive Two‐Boron‐Doped Polycyclic Aromatic Hydrocarbons
Abstract: Embedding two boron atoms into a polycyclic aromatic hydrocarbon (PAH) leads to the formation of a neutral analogue that is isoelectronic to the corresponding dicationic PAH skeleton, which can significantly alter its electronic structure. Based on this concept, we explore herein the identification of near‐infrared (NIR)‐emissive PAHs with the aid of an in silico screening method. Using perylene as the PAH scaffold, we embedded two boron atoms and fused two thiophene rings to it. Based on this design concept, all possible structures (ca. 2500 entities) were generated using a comprehensive structure generator. Time‐dependent DFT calculations were conducted on all these structures, and promising candidates were extracted based on the vertical excitation energy, transition dipole moment, and atomization energy per bond. One of the extracted dithieno‐diboraperylene candidates was synthesized and indeed exhibited emission at 724 nm with a quantum yield of 0.40 in toluene, demonstrating the validity of this screening method. This modification was further applied to other PAHs, and a series of thienobora‐modified PAHs was synthesized.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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In Silico Screening and Experimental Verification of Near‐Infrared‐Emissive Two‐Boron‐Doped Polycyclic Aromatic Hydrocarbons ; day:22 ; month:04 ; year:2024 ; extent:7
Angewandte Chemie ; (22.04.2024) (gesamt 7)
- Creator
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Hattori, Izumi
Hagai, Masaya
Ito, Masato
Sakai, Mika
Narita, Hiroki
Fujimoto, Kazuhiro J.
Yanai, Takeshi
Yamaguchi, Shigehiro
- DOI
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10.1002/ange.202403829
- URN
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urn:nbn:de:101:1-2404231405393.463359933391
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:59 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Hattori, Izumi
- Hagai, Masaya
- Ito, Masato
- Sakai, Mika
- Narita, Hiroki
- Fujimoto, Kazuhiro J.
- Yanai, Takeshi
- Yamaguchi, Shigehiro