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

Spinelli, Floriana; d'Agostino, Simone; Taddei, Paola; Jones, Christopher David; Steed, Jonathan W.; Grepioni, Fabrizia

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.

Citation

Spinelli, F., d'Agostino, S., Taddei, P., Jones, C. D., Steed, J. W., & Grepioni, F. (2018). Activating [4+4] photoreactivity in the solid-state via complexation: from 9-(methylaminomethyl)anthracene to its silver(I) complexes. Dalton Transactions, 16(47), 5725-5733. https://doi.org/10.1039/c8dt00198g

• Journal Article Type: Article
• Acceptance Date: Mar 28, 2018
• Online Publication Date: Mar 29, 2018
• Publication Date: Apr 28, 2018
• Deposit Date: Mar 29, 2018
• Publicly Available Date: Mar 28, 2019
• Journal: Dalton Transactions
• Print ISSN: 1477-9226
• Electronic ISSN: 1477-9234
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 16
• Issue: 47
• Pages: 5725-5733
• DOI: https://doi.org/10.1039/c8dt00198g