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Article: One-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors

TitleOne-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors
Authors
Keywordsaromatic diimides
carbonylation
domino synthesis
organic semiconductors
palladium catalysis
Issue Date2020
Citation
Angewandte Chemie - International Edition, 2020, v. 59, n. 33, p. 14024-14028 How to Cite?
AbstractAromatic diimides are one of the most important chromophores in the construction of n-type organic semiconductors, which lag far behind their p-type counterpart but are necessary for ambipolar transistors, p-n junctions and organic complementary circuits. Herein, we establish a facile one-pot domino synthetic protocol for aromatic diimides via palladium-catalyzed carbonylation of tetrabromo aromatic precursors. Taking tetrabromocorannulene (TBrCor) and tetrabromo-2,7-di-tert-butylpyrene (TBrPy) as the typical examples, we obtained diimide derivatives in yields of about 50 %, one order of magnitude higher than that of the traditional multi-step diimidization. As demonstrated in the case of corannulene diimide, the efficient diimidization not only allows the LUMO levels to be lowered significantly but also provides an ordered and closer packing structures, opening up possibilities to the development of n-type semiconducting materials based on a variety of aromatic systems.
Persistent Identifierhttp://hdl.handle.net/10722/341276
ISSN
2023 Impact Factor: 16.1
2023 SCImago Journal Rankings: 5.300
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorFu, Xiaolong-
dc.contributor.authorZhen, Yonggang-
dc.contributor.authorNi, Zhenjie-
dc.contributor.authorLi, Yang-
dc.contributor.authorDong, Huanli-
dc.contributor.authorSiegel, Jay S.-
dc.contributor.authorHu, Wenping-
dc.date.accessioned2024-03-13T08:41:32Z-
dc.date.available2024-03-13T08:41:32Z-
dc.date.issued2020-
dc.identifier.citationAngewandte Chemie - International Edition, 2020, v. 59, n. 33, p. 14024-14028-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/341276-
dc.description.abstractAromatic diimides are one of the most important chromophores in the construction of n-type organic semiconductors, which lag far behind their p-type counterpart but are necessary for ambipolar transistors, p-n junctions and organic complementary circuits. Herein, we establish a facile one-pot domino synthetic protocol for aromatic diimides via palladium-catalyzed carbonylation of tetrabromo aromatic precursors. Taking tetrabromocorannulene (TBrCor) and tetrabromo-2,7-di-tert-butylpyrene (TBrPy) as the typical examples, we obtained diimide derivatives in yields of about 50 %, one order of magnitude higher than that of the traditional multi-step diimidization. As demonstrated in the case of corannulene diimide, the efficient diimidization not only allows the LUMO levels to be lowered significantly but also provides an ordered and closer packing structures, opening up possibilities to the development of n-type semiconducting materials based on a variety of aromatic systems.-
dc.languageeng-
dc.relation.ispartofAngewandte Chemie - International Edition-
dc.subjectaromatic diimides-
dc.subjectcarbonylation-
dc.subjectdomino synthesis-
dc.subjectorganic semiconductors-
dc.subjectpalladium catalysis-
dc.titleOne-Pot Domino Carbonylation Protocol for Aromatic Diimides toward n-Type Organic Semiconductors-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/anie.202003179-
dc.identifier.pmid32396268-
dc.identifier.scopuseid_2-s2.0-85086153501-
dc.identifier.volume59-
dc.identifier.issue33-
dc.identifier.spage14024-
dc.identifier.epage14028-
dc.identifier.eissn1521-3773-
dc.identifier.isiWOS:000538534300001-

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