Solid-state hydrogen bonded assembly of N,N′-bis(glycinyl)-pyromellitic diimide with aromatic guests

Abstract

The compound N,N′-bis(glycinyl)pyromellitic diimide (L) forms inclusion compounds with aromatic hydrocarbons such as anthracene (D1), phenanthrene (D2) and perylene (D3) as well as tetrathiafulvalene (D4). The aromatic guest molecules are held in the spaces between the aromatic units of extended self-assembly of L derived from the hydrogen bonding between the carboxylic acid end groups of L. The crystal structures of each of these inclusion compounds are determined along with the parent compound L. A R44(12) hydrogen bond pattern involving the carboxylic groups and two bridging methanol molecules is observed in the anthracene inclusion compound of L, whereas in the case of other inclusion compounds conventional R22(8) type hydrogen bonding is observed. While forming inclusion compounds of L with tetrathiafulvalene, the carboxylic acid of L has R22(8) and C11(3) types of hydrogen bonding patterns in the lattice. Preferential inclusion compound formation of L with anthracene over isomeric phenanthrene is observed.