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

0572146 - FZÚ 2024 RIV US eng J - Journal Article
Wang, T. - Angulo-Portugal, P. - Berdonces-Layunta, A. - Jančařík, A. - Gourdon, A. - Holec, J. - Kumar, Manish - Soler Polo, Diego Manuel - Jelínek, Pavel - Casanova, D. - Corso, M. - de Oteyza, D.G. - Calupitan, J.P.
Tuning the diradical character of pentacene derivatives via non- benzenoid coupling motifs.
Journal of the American Chemical Society. Roč. 145, č. 18 (2023), s. 10333-10341. ISSN 0002-7863. E-ISSN 1520-5126
R&D Projects: GA ČR(CZ) GX20-13692X
Research Infrastructure: e-INFRA CZ - 90140; CzechNanoLab II - 90251
Institutional support: RVO:68378271
Keywords : pentacene derivatives * non-benzenoid coupling
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 15, year: 2022
Method of publishing: Open access

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.
Permanent Link: https://hdl.handle.net/11104/0345547