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Diels–Alder reaction on perylenediimides: synthesis and theoretical study of core-expanded diimides


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Title:
Diels–Alder reaction on perylenediimides: synthesis and theoretical study of core-expanded diimides
Authors:
Zink Lorre, Nathalie
Doncel-Giménez, Azahara  
Font-Sanchis, Enrique  
Calbo, Joaquín  
Sastre-Santos, Ángela
Ortí, Enrique
Fernández-Lázaro, Fernando
Editor:
Royal Society of Chemistry
Department:
Departamentos de la UMH::Farmacología, Pediatría y Química Orgánica
Issue Date:
2019
URI:
https://hdl.handle.net/11000/31046
Abstract:
A one-step reaction for the fusion of aromatic rings to one or both bay areas of perylenediimides using benzynes is presented. Yields as high as 70% for naphthoperylenendiimide 2 and 80% for dibenzocoronenediimide 3 are obtained. The reaction is also carried out using substituted benzynes, heteroaromatic benzynes and substituted perylenediimides. A combined experimental/theoretical approach, based on measuring redox and absorption/emission properties and performing density functional theory calculations, indicates that increasing the π-skeleton of PDIs transversally leads to significant and unexpected changes in the electronic, redox and optical properties. The observed trends are rationalized in terms of molecular orbital topology and overlap according to three different levels of core expansion, and can be used as design principles for obtaining PDIs with improved functionalities.
Type of document:
application/pdf
Access rights:
info:eu-repo/semantics/closedAccess
DOI:
https://doi.org/10.1039/c9qo00682f
Appears in Collections:
Artículos Farmacología, Pediatría y Química Orgánica



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