Study of Energy Transfer in Supramolecular Homochiral [2.2]Paracyclophane Self-assembly

Alejandra Hermosilla Palacios, Danielle Fagnani, William Henderson, Ronald Castellano, and Valeria D. Kleiman

Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200

Study of Energy Transfer in Supramolecular Homochiral [2.2]Paracyclophane Self-assembly

Alejandra Hermosilla Palacios, Danielle Fagnani, William Henderson, Ronald Castellano, and Valeria D. Kleiman

Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200

It has been more than sixty years since the discovery of paracyclophanes (pCp) yet they have been unexplored as supramolecular constructs. Two short carbon bridges hold two benzene rings allowing efficient through-space interactions between them. Paracyclophane-4,7,12,15-tetracarboxamide (pCpTA) was synthetized showing intra and intermolecular hydrogen bonding, leading to formation of homochiral and one-dimensional helically laced stacks. This small molecule offers advantages over polymers such as ease of synthesis and purification, higher charge carrier mobilities and is not affected by batch-to-batch properties variations. Steady state absorption measurements have been performed to understand assembly formation, along with temperature dependent measurements. In addition, fluorescence quenching experiments have been carried out comparing stack formation and no stack formation quenching dynamics. Thus giving insight about the energy transfer in the stack. A better understanding of the mechanism can be used to design efficient devices with the help of these studies.