Crystallographic Studies of Supramolecular Synthons in Amine Solvates of trans-1,5-Dichloro-9,10-diethynyl-9,10- dihydroanthracene-9,10-diol

Abstract

Solvent inclusion in organic crystals is quite uncommon, as it is observed in only 15% of cases. Solvation could be imagined to result from the interruption of the “normal” crystallization process because of the preferential formation of directional hydrogen bonds between the included solvent and the organic component. However, it is surprising to note that only a limited number of studies have been performed using amine based solvents, yet amines, next to hydroxyl groups, are the most extensively studied functional group in the field of crystal engineering. In this work, we attempt to determine a correlation between molecular functionality and crystal structures among the 15 different pseudopolymorphs of 1,5-dichloro-trans-9,10-diethynyl-9,10-dihydroanthracene-9,10-diol (DDDA). This work aims to gain an insight into the interaction hierarchy between four molecular functionalities of a solvent molecule, namely, a hydroxy group (benzylic), an ethynyl group, an aromatic chlorine atom, and an amino group and the DDDA molecule.