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Novel fluorinated amino-stilbenes and their solid-state photodimerization

2010; Royal Society of Chemistry; Volume: 34; Issue: 11 Linguagem: Inglês

10.1039/c0nj00264j

1369-9261

Antonio Papagni, Paola Del Buttero, Chiara Bertarelli, L. Miozzo, Massimo Moret, Mary T. Pryce, Silvia Rizzato,

Luminescence and Fluorescent Materials

We synthesized a series of polyfluoro-amino-stilbenes in satisfactory yields by Wittig reaction of 4-piperazinyl-benzalhehydes with pentafluoro-benzylidene-triphenyl-phosphorane and we analyzed the photochemical behavior of these stilbenes in the solid state; thanks to arene–perfluoroarene π–π interactions, some of them have shown a good propensity to give the corresponding cyclobutane photodimers in quantitative yields. The photocyclization is reversible both in solution and in polymeric matrix, affording the corresponding stilbenes with different cis–trans stereo-selectivity.