Synthesis and characterization of a $π$-extended Clar's goblet
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arXiv
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| Main Authors: | , , , , , , |
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| Format: | Preprint |
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2025
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| _version_ | 1866908605145415680 |
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| author | Mishra, Shantanu Vilas-Varela, Manuel Rončević, Igor Paschke, Fabian Albrecht, Florian Gross, Leo Peña, Diego |
| author_facet | Mishra, Shantanu Vilas-Varela, Manuel Rončević, Igor Paschke, Fabian Albrecht, Florian Gross, Leo Peña, Diego |
| contents | Concealed non-Kekulé polybenzenoid hydrocarbons have no sublattice imbalance yet cannot be assigned a classical Kekulé structure, leading to an open-shell ground state with potential application in organic spintronics. They constitute an exceedingly small fraction of the total number of polybenzenoid hydrocarbons that can be constructed for a given number of benzenoid rings, and their synthesis remains challenging. The archetype of such a system is Clar's goblet (C$_{38}$H$_{18}$), a diradical proposed by Erich Clar in 1972 and recently synthesized on a Au(111) surface. Here, we report the synthesis of a pi-extended Clar's goblet (C$_{76}$H$_{26}$), a tetraradical concealed non-Kekulé polybenzenoid hydrocarbon, by a combined in-solution and on-surface synthetic approach. By means of low-temperature scanning tunneling microscopy and atomic force microscopy, we characterized individual molecules adsorbed on a Cu(111) surface. We provide insights into the electronic properties of this elusive molecule, including the many-body nature of its ground and excited states, by mean-field and multiconfigurational quantum chemistry calculations. |
| format | Preprint |
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arxiv_https___arxiv_org_abs_2505_03289 |
| institution | arXiv |
| publishDate | 2025 |
| record_format | arxiv |
| spellingShingle | Synthesis and characterization of a $π$-extended Clar's goblet Mishra, Shantanu Vilas-Varela, Manuel Rončević, Igor Paschke, Fabian Albrecht, Florian Gross, Leo Peña, Diego Mesoscale and Nanoscale Physics Concealed non-Kekulé polybenzenoid hydrocarbons have no sublattice imbalance yet cannot be assigned a classical Kekulé structure, leading to an open-shell ground state with potential application in organic spintronics. They constitute an exceedingly small fraction of the total number of polybenzenoid hydrocarbons that can be constructed for a given number of benzenoid rings, and their synthesis remains challenging. The archetype of such a system is Clar's goblet (C$_{38}$H$_{18}$), a diradical proposed by Erich Clar in 1972 and recently synthesized on a Au(111) surface. Here, we report the synthesis of a pi-extended Clar's goblet (C$_{76}$H$_{26}$), a tetraradical concealed non-Kekulé polybenzenoid hydrocarbon, by a combined in-solution and on-surface synthetic approach. By means of low-temperature scanning tunneling microscopy and atomic force microscopy, we characterized individual molecules adsorbed on a Cu(111) surface. We provide insights into the electronic properties of this elusive molecule, including the many-body nature of its ground and excited states, by mean-field and multiconfigurational quantum chemistry calculations. |
| title | Synthesis and characterization of a $π$-extended Clar's goblet |
| topic | Mesoscale and Nanoscale Physics |
| url | https://arxiv.org/abs/2505.03289 |