Journal
DALTON TRANSACTIONS
Volume 47, Issue 16, Pages 5725-5733Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8dt00198g
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- University of Bologna
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The [4 + 4] photoreactivity of the anthracene derivative 9-(methylaminomethyl)anthracene (MAMA) has been investigated in solution, gel medium and in the solid state. While quantitative formation of the cyloaddition photoproduct was achieved upon irradiation at lambda = 365 nm of ethanol solutions of MAMA, only partial and slow conversion was detected in gels of low molecular weight gelators, and solid-state reactivity was not observed due to the unfavourable relative orientation of the anthracene moieties in the crystal. In hexafluorophosphate, tetrafluoroborate and nitrate silver(i) complexes, however, 9-(methylaminomethyl)anthracene exhibits a more favourable mutual orientation for the aromatic fragments, and [4 + 4] photoreactivity resulted. All compounds were structurally characterized via single crystal and/or X-ray powder diffraction and by Raman spectroscopy; this last technique proved effective in detection of the photoproduct in all solid state complexes.
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