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

doi:10.1039/c8dt00198g

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

Authors

Floriana Spinelli

Simone d'Agostino

Paola Taddei

Christopher David Jones

Professor Jonathan Steed jon.steed@durham.ac.uk
Professor

Fabrizia Grepioni

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