Crystal structures of amarine and isoamarine and copper(I) coordination chemistry with their allylation products

Abstract: The crystal structures of amarine (1) and isoamarine (2), important intermediates in the preparation of 1,2-diphenyl-diaminoethane, were successfully determined. Their allylation products, 1,3-diallyl amarine (1)(CH2 ph name="dbnd" />CH2)2Br (3) and isoamarine bromide (2)(CH2 ph name="dbnd" />CH2)2Br (4) [the crystal structures of (1)(CH2 ph name="dbnd" />CH2)2PF6(3-Br+PF6) and (2)(CH2 ph name="dbnd" />CH2)2PF6 (4-Br+PF6) are also successfully determined to confirm allylation products], react with CuBr to afford (1)2(CH2 ph name="dbnd" />CH2)4(Cu2Br4) (5) and (2)(CH2 ph name="dbnd" />CH2)2(Cu2Br3) (6), respectively. Crystal structures of 5 and 6 reveal that 5 is an anion discrete complex without olefin moiety coordination, and 6 has a 1D infinite chain with olefin moiety coordination as a bridging spacer. The fluorescent emission spectra of 5 (λ emax =570nm) and 6 (λ emax =642nm) were measured, and display a significant difference that can be used for solid state fluorescent sensing them. [Copyright &y& Elsevier]