RT Journal Article
T1 Generating antiaromaticity in polycyclic conjugated hydrocarbons by thermally selective skeletal rearrangements at interfaces
A1 Pérez-Elvira, Elena
A1 Barragán, Ana
A1 Chen, Qifan
A1 Soler-Polo, Diego
A1 Sánchez-Grande, Ana
A1 Vicent, Diego
A1 Lauwaet, Koen
A1 Santos Barahona, José Manuel
A1 Mutombo, Pingo
A1 Mendieta-Moreno, Jesús I.
A1 Torre, Bruno de la
A1 Gallego, José M.
A1 Miranda, Rodolfo
A1 Martín, Nazario
A1 Martín León, Nazario
A1 Jelínek, Pavel
A1 Urgel, José I.
A1 Écija, David
AB Antiaromatic polycyclic conjugated hydrocarbons (PCHs) are attractive research targets in modern organic chemistry in view of their interesting structural, electronic and magnetic properties. Unlike aromatic compounds, the synthesis of antiaromatic PHs is challenging as a result of their high reactivity and lack of stability, stemming from the small energy gap between their highest occupied and lowest unoccupied molecular orbitals. In this work, we describe a strategy toward the introduction of antiaromatic units in PHs via thermally selective intra- and intermolecular ring-rearrangement reactions of dibromomethylene-functionalized molecular precursors upon sublimation on a hot Au(111) metal surface, not available in solution chemistry. The synthetic value of these reactions is proven by 1) the integration of pentalene segments into acene-based precursors which undergo intramolecular ring-rearrangement; 2) the formation of π-conjugated ladder polymers, linked through cyclobutadiene connections, through ring-rearrangement and homocoupling reactions of indenofluorene-based precursors. The elucidation of the reaction products of the title reactions are investigated by scanning tunneling and noncontact atomic force microscopy investigations, and the mechanistic insights are unveiled by state-of-the-art computational studies
PB Nature Springer
SN 2731-0582
YR 2023
FD 2023
LK https://hdl.handle.net/20.500.14352/92016
UL https://hdl.handle.net/20.500.14352/92016
LA eng
NO Pérez-Elvira, E., Barragán, A., Chen, Q. et al. Generating antiaromaticity in polycyclic conjugated hydrocarbons by thermally selective skeletal rearrangements at interfaces. Nat. Synth 2, 1159–1170 (2023). https://doi.org/10.1038/s44160-023-00390-8
NO Comunidad de Madrid
NO Ministerio de Ciencia, Innovacion y Universidades (España)
NO European Commission
NO CzechNanoLab Research Infrastructure
NO Ministry of Education, Youth and Sports of the Czech Republic
DS Docta Complutense
RD 6 abr 2025