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Studies on the photocyclization reaction of 8‐styryl‐substituted coralyne derivatives
Author(s) -
Pithan Phil Marvin,
Ihmels Heiko
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3858
Subject(s) - chemistry , isomerization , cationic polymerization , photochemistry , derivative (finance) , double bond , absorption (acoustics) , medicinal chemistry , organic chemistry , catalysis , physics , acoustics , financial economics , economics
The photoreactivity of four 8‐styryl‐substituted coralyne derivatives was examined by UV/VIS‐ and 1 H‐NMR‐spectroscopy. Except for the dimethylamino‐substituted derivative, these cationic azoniaheterocyclic dyes undergo photocyclization that most likely proceeds through an initial E ‐ Z ‐isomerization of the double bond. Subsequent oxidation of the intermediates under aerobic conditions gave the pyrrolo‐annelated quinolizinium derivatives as final products, thus providing a useful synthetic route to polycyclic azoniahetarene derivatives. The 6‐(4‐chlorophenyl)‐substituted pyrroloquinolizinium derivative was isolated on a preparative scale, and the investigation of its photophysical properties revealed significantly red‐shifted absorption ( λ abs = 465–480 nm) and emission bands ( λ fl = 550–562 nm) in comparison to the parent coralyne and the styryl‐substituted derivatives.