Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2,9-Bis(4-hydroxyphenyl)-1,10-phenanthroline, alpha,omega-Dibromides, and Resorcinol or 2,7-Dihydroxynaphthalene Academic Article uri icon


  • 1,3-Bis(6-bromohexyloxy)benzene, 2,7-bis(6-bromohexyloxy)naphthalene, 1,3-bis(4-bromomethylbenzyloxy)benzene, and 1,3-bis(3-bromomethylbenzyloxy)benzene were prepared via Williamson ether synthesis using resorcinol or 2,7-dihydroxynaphthalene and 1,6-dibromohexane, 1,4-bis(bromomethyl)benzene, or 1,3-bis(bromomethyl)benzene (2147% yield). These dibromides were condensed with 2,9-bis(4-hydroxyphenyl)-1,10-phenanthroline in the presence of K2CO3 to give the corresponding 31- to 35-membered macrocycles (3ad, 2263% yield). When 3ad were treated with CuI, mononuclear 1:1 complexes formed, in which the CuI chelates to the nitrogen donor atoms of the phenanthroline moiety (4ad, 4080% yield). The crystal structures of 3ac and 4ac were determined and analyzed using density functional theory calculations and in the context of rotaxanes that could be formed by treatment of 4ad with terminal alkynes (e.g. macrocycle dimensions, void volumes). The copper and iodide atoms in 4ac significantly protrude from the least-squares plane of the phenanthroline moiety (0.460.63 and 1.652.07 ).

published proceedings


author list (cited authors)

  • Baranova, Z., Amini, H., Neupane, M., Garrett, S. C., Ehnbom, A., Bhuvanesh, N., Reibenspies, J. H., & Gladysz, J. A.

citation count

  • 2

complete list of authors

  • Baranova, Zuzana||Amini, Hashem||Neupane, Madhav||Garrett, Sydney C||Ehnbom, Andreas||Bhuvanesh, Nattamai||Reibenspies, Joseph H||Gladysz, John A

publication date

  • January 2017