Syntheses, Solid State Structures and Photochemistry of ,-Bis-[(1,8-dichloroanthracen-10-yl)dimethylsilyl]alkanes

Niermeier P, Lamm J-H, Linnemannstöns M, Neumann B, Stammler H-G, Mitzel NW. Syntheses, Solid State Structures and Photochemistry of ,-Bis-[(1,8-dichloroanthracen-10-yl)dimethylsilyl]alkanes. SYNTHESIS-STUTTGART. 2018;50(15):3041-3047.Starting from 10-bromo-1,8-dichloroanthracene, a series of 1,8-dichlorinated anthracene derivatives, flexibly bridged in position 10 by -Me (2) Si- and -Me (2) Si-(CH (2) ) (n) -SiMe (2) - linker units, were synthesised. The linked anthracenes were generated by converting (1,8-dichloroanthracen-10-yl)lithium with chlorosilanes in salt-elimination reactions. The bichromophors were tested in UV light induced photo reactions. None of the new compounds yielded any intra- or intermolecular photoproduct. All ,-(dimethylsilyl)alkane-linked bisanthracenes decomposed to give 1,8-dichloro-9-hydroxyanthracen-10(9 H )-one in the presence of oxygen. A completely different behaviour was shown by the bisanthracenyldimethylsilane, undergoing a 9,10:3,4-photocyclomerisation reaction. The new compounds were characterised by NMR spectroscopy, mass spectrometry and in most cases by X-ray diffraction studies