Reductive Doping Inhibits the Formation of Isomerization‐Derived Structural Defects in N‐doped Poly (benzodifurandione) (n‐PBDF)
Abstract: Recently, solution‐processable n‐doped poly (benzodifurandione) (n‐PBDF) has been made through in‐situ oxidative polymerization and reductive doping, which exhibited exceptionally high electrical conductivities and optical transparency. The discovery of n‐PBDF is considered a breakthrough in the field of organic semiconductors. In the initial report, the possibility of structural defect formation in n‐PBDF was proposed, based on the observation of structural isomerization from (E)‐2H,2′H‐[3,3′‐bibenzofuranylidene]‐2,2′‐dione (isoxindigo) to chromeno[4,3‐c]chromene‐5,11‐dione (dibenzonaphthyrone) in the dimer model reactions. In this study, we present clear evidence that structural isomerization is inhibited during polymerization. We reveal that the dimer (BFD1) and the trimer (BFD2) can be reductively doped by several mechanisms, including hydride transfer, forming charge transfer complexes (CTC) or undergoing an integer charge transfer (ICT) with reactants available during polymerization. Once the hydride transfer adducts, the CTC, or the ICT product forms, structural isomerization can be effectively prevented even at elevated temperatures. Our findings provide a mechanistic understanding of why isomerization‐derived structural defects are absent in n‐PBDF backbone. It lays a solid foundation for the future development of n‐PBDF as a benchmark polymer for organic electronics and beyond.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Reductive Doping Inhibits the Formation of Isomerization‐Derived Structural Defects in N‐doped Poly (benzodifurandione) (n‐PBDF) ; day:27 ; month:03 ; year:2024 ; extent:9
Angewandte Chemie / International edition. International edition ; (27.03.2024) (gesamt 9)
- Urheber
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Hwang, Jinhyo
Zhao, Qiyuan
Ahmed, Mustafa
Yakisan, Alexander C.
Espenship, Michael F.
Laskin, Julia
Savoie, Brett M.
Mei, Jianguo
- DOI
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10.1002/anie.202401465
- URN
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urn:nbn:de:101:1-2024032713433211092819
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 10:52 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Hwang, Jinhyo
- Zhao, Qiyuan
- Ahmed, Mustafa
- Yakisan, Alexander C.
- Espenship, Michael F.
- Laskin, Julia
- Savoie, Brett M.
- Mei, Jianguo
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