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We herein report the preparation of constitutional isomers of brominated-functionalized pillar[5]arenes via co-condensation of 1,4-bis(2-bromoethoxy)benzene and 1,4-dimethoxybenzene. The structures of the obtained isomers were then established using single crystal X-ray diffraction. We also found that the isomeric yield distribution of the different constitutional isomers was independent of the monomer's mole feed ratio, as revealed by HPLC analysis of the crude mixture. Finally, further characterization of the separated constitutional isomers indicated that they possess different melting points, NMR spectra, crystal structures, binding constants and stacking patterns in the solid state.

Constitutional isomers of brominated-functionalized copillar[5]arenes: synthesis, characterization, and crystal structures