Mechanically Interlocked Water-Soluble Pd₆ Host for the Selective Separation of Coal Tar-Based Planar Aromatic Molecules

Abstract

Research on the synthesis of catenated cages has been a growing field of interest in the past few years. While multiple types of catenated cages with different structures have been synthesized, the application of such systems has been much less explored. Specifically, the use of catenated cages in the separation of industrially relevant molecules that are present in coal tar has not been explored before. Herein, we demonstrate the use of a newly synthesized interlocked cage 1 [C 184 H 240 N 76 O 48 Pd 6 ] (M 6 L 4 ), formed through the self-assembly of ligand L.HNO 3 (tris(4-(1H-imidazole-1yl)benzylidene)hydrazine-1-carbohydrazonhydrazide) with acceptor cis-[(tmchda)Pd-(NO 3 ) 2 ] [tmchda = ±N,N,N′,N′-tetramethylcyclohexane-1,2-diamine] (M). The interlocked cage 1 was able to separate the isomers (anthracene and phenanthrene) using a simple solvent extraction technique. Using the same technique, the much more difficult separation of structurally and physiochemically similar compounds acenaphthene and acenaphthylene was performed for the first time with 1 as the host. Other noninterlocked hexanuclear Pd 6 cages having a wider cavity proved inefficient for such separation, demonstrating the uniqueness of the interlocked cage 1 for such challenging separation.