Activating [4 + 4] photoreactivity in the solid-state via complexation: from 9-(methylaminomethyl)anthracene to its silver(i) complexes. Issue 16 (10th April 2018)

• Record Type: Journal Article
• Authors: Spinelli, Floriana; d'Agostino, Simone; Taddei, Paola; Jones, Christopher D.; Steed, Jonathan W.; Grepioni, Fabrizia
• Is Part Of: Dalton transactions. Volume 47:Issue 16(2018)
• Page Start: 5725
• Page End: 5733
• Publication Date: 2018-04-10
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c8dt00198g
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Photoreactivity of an otherwise photostable anthracene derivative can be observed in the solid state upon complexation to silver(i ) salts. 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.