Studying an antiaromatic polycyclic hydrocarbon adsorbed on different surfaces

Zsolt Majzik (), Niko Pavliček, Manuel Vilas-Varela, Dolores Pérez, Nikolaj Moll, Enrique Guitián, Gerhard Meyer, Diego Peña () and Leo Gross
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Zsolt Majzik: IBM Research - Zurich
Niko Pavliček: IBM Research - Zurich
Manuel Vilas-Varela: Universidade de Santiago de Compostela
Dolores Pérez: Universidade de Santiago de Compostela
Nikolaj Moll: IBM Research - Zurich
Enrique Guitián: Universidade de Santiago de Compostela
Gerhard Meyer: IBM Research - Zurich
Diego Peña: Universidade de Santiago de Compostela
Leo Gross: IBM Research - Zurich

Nature Communications, 2018, vol. 9, issue 1, 1-6

Abstract: Abstract Antiaromatic and open-shell molecules are attractive because of their distinct electronic and magnetic behaviour. However, their increased reactivity creates a challenge for probing their properties. Here, we describe the on-surface and in-solution generation and characterisation of a highly reactive antiaromatic molecule: indeno[1,2-b]fluorene (IF). In solution, we generated IF by KI-induced dehalogenation of a dibromo-substituted precursor molecule and found that IF survives for minutes at ambient conditions. Using atom manipulation at low temperatures we generated IF on Cu(111) and on bilayer NaCl. On these surfaces, we characterised IF by bond-order analysis using non-contact atomic force microscopy with CO-functionalised tips and by orbital imaging using scanning tunnelling microscopy. We found that the closed-shell configuration and antiaromatic character predicted for gas-phase IF are preserved on the NaCl film. On Cu(111), we observed significant bond-order reorganisation within the s-indacene moiety because of chemisorption, highlighting the importance of molecule surface interactions on the π-electron distribution.

Date: 2018
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DOI: 10.1038/s41467-018-03368-9

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