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Cyclopenta Ring Fused Bisanthene and Its Charged Species with Open‐Shell Singlet Diradical Character and Global Aromaticity/ Anti‐Aromaticity
Author(s) -
Wang Qing,
Gopalakrishna Tullimilli Y.,
Phan Hoa,
Herng Tun Seng,
Dong Shaoqiang,
Ding Jun,
Chi Chunyan
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704805
Subject(s) - aromaticity , diradical , annulene , singlet state , delocalized electron , chemistry , dication , ring (chemistry) , open shell , ground state , antiaromaticity , computational chemistry , photochemistry , molecule , physics , organic chemistry , atomic physics , excited state
Cyclopenta ring fused bisanthene and its charged species were synthesized. The neutral compound has an open‐shell singlet ground state and displays global anti‐aromaticity. The dication also exhibits singlet diradical character but has a unique [10]annulene‐within‐[18]annulene global aromatic structure. The dianion is closed‐shell singlet in the ground state and shows global aromaticity with 22 π electrons delocalized on the periphery. These findings prrovide new insight into the design and properties of global aromatic/anti‐aromatic systems based on π‐conjugated polycyclic hydrocarbons.