In by admin

Name Ms. Danielle Fagnani
Organization University of Florida
Type Poster
Topic PMSE/POLY
Title

SELF-ASSEMBLING PARACYCLOPHANES

Author(s)

Danielle E. Fagnani, Yu Zhu, Will R. Henderson, and Ronald K. Castellano

Author Location(s)

Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville FL 32611-7200, USA

Abstract

Paracyclophanes are an interesting class of compounds owing to their rare structural, chemical, optical, and physical properties. [2.2]Paracyclophane (pCp), an exemplar from this class of compounds, has fascinated researchers for decades, but has been virtually unexplored in supramolecular constructs. Recently, we have developed a new hydrogen-bond capable pCp derivative, pCp-4,7,12,15-tetracarboxamide ((±)-pCpTA), and an accompanying self-assembly strategy to uniquely promote the formation of π-stacked pCp nanorods. The crystal structure of (±)-pCpTA confirms the formation of the intended design: one-dimensional stacking promoted by cooperative transannular and intermolecular hydrogen bonds that helically “lace-up” the structure. Furthermore, each stack is homochiral, as dictated by the planar chirality of the monomer (Rp- or Sp-pCpTA), highlighting the stereospecific self-recognition capabilities of (±)-pCpTA. A combination of NMR, IR, and UV-Vis studies indicates the formation of aggregated species and characteristic properties of supramolecular polymers in solution. Current efforts, the focus of this poster, include the chiral resolution of the pCpTA monomers, incorporation of stronger hydrogen bonding units, and extension of the self-assembly design to [3.3]paracyclophane.