Tuning the diradical character of pentacene derivatives via non-benzenoid coupling motifs

The development of functional organic molecules requires structures of increasing size and complexity, which are typically obtained by the covalent coupling of smaller building blocks. Herein, with the aid of high-resolution scanning tunneling microscopy/spectroscopy and density functional theory, t...

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Detalles Bibliográficos
Autores: Wang, Tao, Angulo Portugal, Paula, Berdonces-Layunta, Alejandro, Jancarik, Andrej, Gourdon, André, Holec, Jan, Kumar, Manish, Soler Polo, Diego, Jelinek, Pavel, Casanova, David, Corso, Martina, Oteyza, Dimas G. de, Calupitan, Jan Patrick
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/337939
Acceso en línea:http://hdl.handle.net/10261/337939
Access Level:acceso abierto
Descripción
Sumario:The development of functional organic molecules requires structures of increasing size and complexity, which are typically obtained by the covalent coupling of smaller building blocks. Herein, with the aid of high-resolution scanning tunneling microscopy/spectroscopy and density functional theory, the coupling of a sterically demanded pentacene derivative on Au(111) into fused dimers connected by non-benzenoid rings was studied. The diradical character of the products was tuned according to the coupling section. In particular, the antiaromaticity of cyclobutadiene as the coupling motif and its position within the structure play a decisive role in shifting the natural orbital occupancies toward a stronger diradical electronic character. Understanding these structure–property relations is desirable not only for fundamental reasons but also for designing new complex and functional molecular structures.

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