Abstract
The development of supramolecular synthons capable of driving hierarchical two-dimensional (2D) self-assembly is an important step toward the growth of complex and functional molecular surfaces. In this work, the formation of nucleobase quartets consisting of adenine and thymine groups was used to control the 2D self-assembly of porphyrins. Tetra-(phenylthymine) zinc porphyrin (Zn-tetra-TP) and tetra-(phenyladenine) porphyrin (tetra-AP) were synthesized, and scanning tunneling microscopy (STM) experiments were performed to visualize their self-assembly at the liquid–solid interface between an organic solvent and a graphite surface. Monocomponent solutions of both Zn-tetra-TP and tetra-AP form stable 2D structures with either thymine–thymine or adenine–adenine hydrogen bonding. Structural models based on STM data were validated using molecular mechanics (MM) simulations. In contrast, bicomponent mixtures showed the formation of a structure with p4 symmetry consisting of alternating Zn-tetra-TP and tetra-AP...
Highlights
The use of recognition interactions to control the two-dimensional (2D) self-assembly of molecules provides a route to form complex and potentially functional nanostructured surfaces.13 In combination with the molecular resolution of surfaces provided by scanning tunneling microscopy (STM) this goal has been the driving force behind a wealth of research activity.3-6 These studies use concepts from reticular synthesis7 and molecular tectonics.8 Rigid and planar molecular building blocks known as tectons are decorated with functional groups at specific positions
molecular mechanics (MM) simulations suggest that hydrogen bonding inter-actions within these structures are based on the formation of adenine-thymine (ATAT) quartets with Watson-Crick base pairing between adenine and thymine groups
Tetra-AP was found to be sparingly soluble in DMSO with lower solubility in other common organic solvents, behaviour similar to that observed for tetra-TP.44
Summary
The use of recognition interactions to control the two-dimensional (2D) self-assembly of molecules provides a route to form complex and potentially functional nanostructured surfaces. In combination with the molecular resolution of surfaces provided by scanning tunneling microscopy (STM) this goal has been the driving force behind a wealth of research activity. These studies use concepts from reticular synthesis and molecular tectonics. Rigid and planar molecular building blocks known as tectons are decorated with functional groups at specific positions. The use of recognition interactions to control the two-dimensional (2D) self-assembly of molecules provides a route to form complex and potentially functional nanostructured surfaces.. In combination with the molecular resolution of surfaces provided by scanning tunneling microscopy (STM) this goal has been the driving force behind a wealth of research activity.. In combination with the molecular resolution of surfaces provided by scanning tunneling microscopy (STM) this goal has been the driving force behind a wealth of research activity.3-6 These studies use concepts from reticular synthesis and molecular tectonics.. Recognition interactions between functional groups on different tectons form supramolecular synthons linking the tectons together and driving self-assembly. A key example of the use of hydrogen bonds as molecular recognition interactions in 2D self-assembly is the triple hydrogen bond interaction formed between perylenetetracarboxylic diimide (PTCDI) and melamine. Hydrogen bonds in particular have been widely used as stabilizing interactions for 2D self-assembly. A key example of the use of hydrogen bonds as molecular recognition interactions in 2D self-assembly is the triple hydrogen bond interaction formed between perylenetetracarboxylic diimide (PTCDI) and melamine.
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