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Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational
Joscha Vollmeyer1, Friederike Eberhagen1, Sigurd Höger1
1Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany.
Beilstein Journal of Organic Chemistry
|January 1, 2015
Summary
Highly oriented pyrolytic graphite templates the self-assembly of naphthylene-phenylene-acetylene macrocycles. The graphite surface organizes these molecules regardless of their internal nanopore fillings.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Surface Science
Background:
- Shape-persistent macrocycles are crucial for constructing complex supramolecular architectures.
- Controlling the self-assembly of macrocycles at interfaces is key to designing functional materials.
- The influence of internal pore filling on macrocycle organization at solid/liquid interfaces remains an area of interest.
Purpose of the Study:
- To investigate the self-assembly behavior of three naphthylene-phenylene-acetylene macrocycles with varying nanopore fillings.
- To explore the role of highly oriented pyrolytic graphite (HOPG) as a template for macrocycle organization.
- To analyze the impact of molecular structure and pore filling on two-dimensional (2D) crystalline monolayer formation.
Main Methods:
- Utilizing in situ scanning tunneling microscopy (STM) to obtain submolecularly resolved images.
- Self-assembling macrocycles at the solid/liquid interface of HOPG and 1,2,4-trichlorobenzene.
- Analyzing the resulting 2D crystalline monolayer patterns and lattice parameters.
Main Results:
- Three shape-persistent macrocycles with identical backbones but different nanopore fillings were successfully self-assembled.
- Submolecularly resolved STM imaging revealed concentration-dependent conformational polymorphism and distinct packing motifs (open and dense).
- Identical lattice parameters were observed for all three macrocycles, indicating that graphite templating is independent of internal pore structure.
Conclusions:
- Highly oriented pyrolytic graphite effectively templates the organization of naphthylene-phenylene-acetylene macrocycles.
- The size and symmetry of the macrocycles, rather than their internal nanopore fillings, primarily dictate intermolecular distances.
- This study demonstrates graphite's utility as a universal template for macrocycle assembly, irrespective of their specific interior characteristics.
