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We herein describe the synthesis of 3ʹ-aminofluorene-9-spiro5ʹ-imidazolidine-2ʹ,4ʹ-dithione through the reaction of fluorene-9-spiro4ʹ-thiazolidine-2ʹ,5ʹ-dithione with hydrazine, and subsequent investigation of the interactions of the synthesized spirocycle-containing imidazolidinedithione with organic solvents. Recrystallization from a solvent containing benzene led to the formation of an inter-molecular compound consisting of 3ʹ-aminofluorene9-spiro-5ʹ-imidazolidine-2ʹ,4ʹ-dithione and benzene in a 2:1 ratio through both intramolecular N-H∙∙∙S hydrogen bonds and additional weak N-H∙∙∙ interactions. The trapped benzene molecule was reversibly released by dissolution of the inter-molecular compound in acetone and subsequent concentration under reduced pressure at room temperature, and also by heating at 130–150 °C. INTRODUCTION Supramolecular systems comprised of inter-molecular compounds (IMCs) have received growing interest in the context of biometric molecular transport systems and lab-on-a-chip applications, including medical diagnoses, biosensors, bionic computers, and biological networks. In terms of molecular transport, three key technologies have been intensely investigated, namely the directional propagation of transporters, the controlled release of carrier molecules, and transmission/reception systems for transferred carrier molecules. As example carrier molecules, imidazole heterocycles containing oxygen or sulfur heteroatoms have attracted substantial attention due to their potential applications in agrochemical and pharmaceutical areas as anticancer, antibacterial, and antifungal agents. They also tend to exhibit diverse therapeutic abilities. Among these compounds, derivatives of imidazolidine-2-thiones display remarkable biological activities, including antimicrobial, antifungal, antithyroid, antioxidant, HETEROCYCLES, Vol. 96, No. 12, 2018 2087

Reversible Formation of an Inter-Molecular Compound Comprising 3ʹ-Aminofluorene-9-spiro-5ʹ-imidazolidine-2ʹ,4ʹ-dithione and Benzene