Formation and isolation of huge cyclic oligomers: posycondensation of 1,5-bis(1-hydroxy-3,6,9-trioxanonyl) naphthalene and terephthaloyl chloride

Abstract

Polycondensation of 1,5-bis(1-hydroxy-3,6,9-trioxanonyl) naphthalene 3and terephthaloyl chloride 4 gives giant macrocycles, i.e. crownophanes (2n) with 30n(n= 1–5) atom perimeters, in ca. 30%m/m overall yield; owing to self-complementarity by edge–face arene–arene interactions, a packing ratio of 71. 8% is found for 2(1).