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Towards Nonalternant Nanographenes through Self‐Promoted Intramolecular Indenoannulation Cascade by C−F Bond Activation
Author(s) -
Akhmetov Vladimir,
Feofanov Mikhail,
Papaianina Olena,
Troyanov Sergey,
Amsharov Konstantin
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201902586
Subject(s) - intramolecular force , context (archaeology) , cascade , aryl , chemistry , nanotechnology , combinatorial chemistry , materials science , stereochemistry , organic chemistry , biology , paleontology , alkyl , chromatography
Large polycyclic aromatic hydrocarbons (PAHs) containing pentagons represent an important class of compounds that are considered to be superior materials in future nano‐electronic applications. From this perspective, the development of synthetic approaches to large PAHs and nanographenes (NGs) is a matter of great importance. In this context indenoannulation appears to be the most practical way to introduce pentagons into NGs. Here we report that alumina‐mediated C−F bond activation is an attractive tool for the synthesis of non‐alternant NGs bearing several pentagons. The unique nature of the reaction leads to a rather counter‐intuitive outcome and allows considering each previous aryl–aryl coupling as a promoter of the following one, despite the continuous increase in the strain energy. Thus, the presented strategy combines both facile synthesis and significant yields for large nonalternant PAHs and NGs.