RT Journal Article
T1 Enantioselective synthesis of a two-fold inherently chiral molecular nanographene
A1 Buendía, Manuel
A1 Fernández García, Jesús Manuel
A1 Perles Hernáez, Josefina
A1 Filippone, Salvatore
A1 Martín León, Nazario
AB The introduction and precise control of stereogenic elements in chemical structures is typically a challenging task. Most asymmetric methods require the presence of a heteroatom in the starting substrates acting as an anchor point for the successful transfer of chiral information. For this reason, compounds comprising only carbon atoms, such as optically active molecular nanographenes, are usually obtained as racemates, and isolated by chiral chromatographic separation. Here, we report an enantioselective strategy that uses three stereocontrolled synthetic steps to introduce and extend three different types of stereogenic elements, namely central, axial and helicoidal chirality, into a polycyclic aromatic structure. Thus, two chiral nanographene layers are covalently connected through a chiral triindane core. The final stereocontrolled graphitization Scholl reaction affords the formation of chiral nanographene units with remarkable enantiomeric excesses, high stereochemical stability and good chiroptical properties.
PB Springer Nature
YR 2024
FD 2024-02-22
LK https://hdl.handle.net/20.500.14352/120330
UL https://hdl.handle.net/20.500.14352/120330
LA eng
NO Buendía, M.; Fernández-García, J. M.; Perles, J.; Filippone, S.; Martín, N. Enantioselective Synthesis of a Two-Fold Inherently Chiral Molecular Nanographene. Nat. Synth 2024, 3 (4), 545–553. https://doi.org/10.1038/s44160-024-00484-x.
NO M.B., S.F., J.M.F.-G. and N.M. acknowledge financial support from the Spanish MICIN (project PID2020-114653RB-I00), they also acknowledge financial support from the ERC (SyG TOMATTO ERC-2020-951224) and from the ‘(MAD2D-CM)-UCM’ project funded by Comunidad de Madrid, by the Recovery, Transformation and Resilience Plan and by NextGenerationEU from the European Union. M.B. also acknowledges financial support from the Spanish MICIN (project CTQ2017-83531-R). J.P. thanks M. Ramírez and P. Martínez-Martín for their help with the molecular models. We also acknowledge L. Favereau for his help in the CPL measurements at Rennes Institute of Chemical Sciences, Rennes, France.
NO Ministerio de Ciencia, Innovación y Universidades.
NO Comunidad de Madrid
NO Tomatto ERC (EU)
DS Docta Complutense
RD 9 dic 2025