Premium
Tetrabenzo[a,f,j,o]perylene: A Polycyclic Aromatic Hydrocarbon With An Open‐Shell Singlet Biradical Ground State
Author(s) -
Liu Junzhi,
Ravat Prince,
Wagner Manfred,
Baumgarten Martin,
Feng Xinliang,
Müllen Klaus
Publication year - 2015
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.201502657
Subject(s) - perylene , singlet state , zigzag , ground state , polycyclic aromatic hydrocarbon , chemistry , photochemistry , hydrocarbon , molecule , crystallography , physics , atomic physics , organic chemistry , excited state , geometry , mathematics
A novel tetrabenzo[a,f,j,o]perylene, namely “bistetracene” in which two tetracenes are connected side by side with two bonds, was synthesized and characterized. An optical energy gap of about 1.56 eV is derived from the UV/Vis absorption spectrum, showing the low optical gap feature of such zigzag‐edged polycyclic aromatic hydrocarbons (PAHs). Theoretical calculations and physical property investigations manifest that such a PAH possesses a prominent biradical character in the ground state, which is the first example among bistetracene derivatives. However, the bistetracene can easily undergo oxidation to tetrabenzo[a,f,j,o]perylene‐9,19‐dione (diketone) under ambient conditions. Thereby, such zigzag‐edged PAH provides insight into understanding the edge state of other expanded homologues, such as peri‐tetracenes or peri‐pentacenes.