Selective Recognition of Phenazine by 2,6-Dibutoxylnaphthalene-Based Tetralactam Macrocycle

A 2,6-dibutoxylnaphthalene-based tetralactam macrocycle was designed and synthesized. This macrocycle shows highly selective recognition to phenazine – a well-known secondary metabolite in bacteria and an emerging disinfection byproduct in drinking water. In contrast, the macrocycle shows no binding to the structurally similar dibenzo-1,4-dioxin. It was revealed that hydrogen bonding, π-π and σ-π interactions are the major driving forces between phenazine and the new tetralactam macrocycle. A perfect complementarity in electrostatic potential surfaces may explain the high selectivity. In addition, the macrocycle shows fluorescent response to phenazine, demonstrating its potential in fluorescent detection of phenazine.