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A Dipleiadiene‐Embedded Aromatic Saddle Consisting of 86 Carbon Atoms
Author(s) -
Pun Sai Ho,
Chan Chi Kit,
Luo Jiye,
Liu Zhifeng,
Miao Qian
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711437
Subject(s) - moiety , bent molecular geometry , saddle , ring (chemistry) , molecule , naphthalene , crystallography , chemistry , derivative (finance) , aromaticity , stereochemistry , materials science , computational chemistry , organic chemistry , mathematical optimization , mathematics , financial economics , economics
This study presents a new type of negatively curved nanographene (C 86 H 32 ) that contains an unprecedented pattern of heptagons. A tert ‐butylated derivative of C 86 H 32 was successfully synthesized using tetrabenzodipleiadiene as a key building block. This synthesis involved a ring expansion reaction as a key step to form the seven‐membered rings in the framework of tetrabenzodipleiadiene. The single‐crystal structure reveals a saddle‐shaped molecule with a highly bent naphthalene moiety at the center of the polycyclic backbone. As found from the DFT calculations, this aromatic saddle is flexible at room temperature and has a saddle‐shaped geometry as the dominant conformation. The DFT calculations along with experimental results show that the attachment of t ‐butyl groups to the central tetrabenzodipleiadiene moiety of nanographene C 86 H 32 can stabilize the saddle conformation and make this nanographene less flexible.