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Activating [4+4] photoreactivity in the solid-state via complexation : from 9-(methylaminomethyl)anthracene to its silver(I) complexes.

Spinelli, Floriana and d'Agostino, Simone and Taddei, Paola and Jones, Christopher David and Steed, Jonathan W. and Grepioni, Fabrizia (2018) 'Activating [4+4] photoreactivity in the solid-state via complexation : from 9-(methylaminomethyl)anthracene to its silver(I) complexes.', Dalton transactions., 16 (47). pp. 5725-5733.

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.

Item Type:Article
Full text:(AM) Accepted Manuscript
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Status:Peer-reviewed
Publisher Web site:https://doi.org/10.1039/C8DT00198G
Date accepted:28 March 2018
Date deposited:16 April 2018
Date of first online publication:29 March 2018
Date first made open access:28 March 2019

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