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Photochromism in the arylaroylaziridine system
Author(s) -
Padwa Albert,
Hamilton Lewis
Publication year - 1967
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.5570040121
Subject(s) - photochromism , chemistry , photochemistry , ring (chemistry) , absorption (acoustics) , absorption spectroscopy , aziridine , colored , double bond , polymer chemistry , organic chemistry , optics , physics , materials science , composite material
Photochromism of a number of arylaroylaziridines has been observed in the solid state or in the rigid matrix. The photochromic behavior is dependent on the intensity of the incident radiation, the reaction medium, the wavelength of light used and on the relationship of the substituents on the three‐membered ring. From the visible absorption spectra it is clear that cis ‐arylaroylaziridines give different colored species than do the trans isomers. These results suggest that the coloration is due to an extensive electrical interaction between the bent bonds of the aziridine ring and the π orbitals of the benzoyl and phenyl groups. Attempts to trap the colored species by co‐irradiation with substrates containing a multiple bond failed. A reaction has been found to occur upon heating various arylaroylaziridines with dimethylacetylene dicarboxylate in inert solvents.