The olefin metathesis reaction in the synthesis of resorc[4]arenes with intriguing architectures

Tetramerization of (E)-2,4-dimethoxycinnamic acid ω-undecenyl ester with ethereal BF3 gave three stereoisomers which were assigned as the chair, cone, and 1,2-alternate conformations. When the three resorc[4]arenes were submitted to olefin metathesis using the second generation Grubbs catalyst, different intra- and inter-molecular products were isolated, depending on conformation and reaction conditions. Molecular modeling studies showed that a basket-like resorc[4]arene, obtained by olefin metathesis of the cone resorc[4]arene ω-undecenyl ester, provide efficient shape complementarity to fullerenes C60 and C70 . Both self-assembly and encapsulation phenomena were demonstrated by UV spectroscopy.