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A Peri‐tetracene Diradicaloid: Synthesis and Properties
Author(s) -
Ni Yong,
Gopalakrishna Tullimilli Y.,
Phan Hoa,
Herng Tun Seng,
Wu Shaofei,
Han Yi,
Ding Jun,
Wu Jishan
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201804276
Subject(s) - tetracene , diradical , zigzag , singlet state , character (mathematics) , materials science , graphene , singlet fission , derivative (finance) , crystallography , chemistry , nanotechnology , chemical physics , molecule , computational chemistry , triplet state , atomic physics , physics , organic chemistry , geometry , mathematics , financial economics , economics , excited state
Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character ( y 0 =51.5 % by calculation) and a small singlet–triplet gap (Δ E S‐T =−2.5 kcal mol −1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3 .