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 λ = 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.
Activating [4+4] photoreactivity in the solid-state via complexation: from 9-(methylaminomethyl)anthracene to its silver(I) complexes / Floriana Spinelli, Simone d’ Agostino, Paola Taddei, Christopher D. Jones, Jonathan W. Steed, Fabrizia Grepioni. - In: DALTON TRANSACTIONS. - ISSN 1477-9234. - ELETTRONICO. - 47:(2018), pp. 5725-5733. [10.1039/c8dt00198g]
Activating [4+4] photoreactivity in the solid-state via complexation: from 9-(methylaminomethyl)anthracene to its silver(I) complexes.
Floriana Spinelli;Simone d’ Agostino;Paola Taddei;Fabrizia Grepioni
2018
Abstract
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 λ = 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.