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An Unprecedented Photochemical Reaction for Anthracene‐Containing Derivatives
Author(s) -
Zhao JiangLin,
Jiang XueKai,
Wu Chong,
Wang ChuanZeng,
Zeng Xi,
Redshaw Carl,
Yamato Takehiko
Publication year - 2016
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201600783
Subject(s) - anthracene , chemistry , photochemistry , photodissociation , anthraquinone , irradiation , organic chemistry , physics , nuclear physics
A series of anthracene‐containing derivatives have been synthesised and characterised. The photochemical behaviour of these derivatives have been investigated by 1 H NMR spectroscopy. An unprecedented photolysis reaction for anthracene‐containing derivatives was observed in the case of anthracenes directly armed with a ‐CH 2 O‐R group upon UV irradiation. The photolysis reaction process has been demonstrated to occur in three steps. Firstly, the anthracene‐containing derivatives are converted into the corresponding endoperoxide intermediate upon UV irradiation in the presence of air; then, the endoperoxide intermediate is decomposed to the corresponding starting compound and 9‐anthraldehyde; finally, 9‐anthraldehyde is further oxidised to anthraquinone. Additionally, the photolysis reaction of anthracene‐containing derivatives is significantly promoted in the presence of a thiacalix[4]arene platform.