1. Binary Conformational Switches in a Porphyrin Chain: Tautomerization and Stereoisomerization
- Author
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Simone Velari, Zhijing Feng, Carlo Dri, Giovanni Comelli, Maria Peressi, Andrea Goldoni, Feng, Zhijing, Velari, Simone, Dri, Carlo, Goldoni, Andrea, Peressi, Maria, and Comelli, Giovanni
- Subjects
Proton ,Hydrogen ,chemistry.chemical_element ,02 engineering and technology ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Porphyrin ,chemistry.chemical_compound ,Chain (algebraic topology) ,Conformational switch ,Self-assembly ,Scanning tunneling microscopy ,Density Functional Theory ,Physical and Theoretical Chemistry ,021001 nanoscience & nanotechnology ,Tautomer ,0104 chemical sciences ,Surfaces, Coatings and Films ,Electronic, Optical and Magnetic Materials ,General Energy ,chemistry ,Intramolecular force ,Phthalocyanine ,0210 nano-technology ,Derivative (chemistry) - Abstract
In the last decade, hydrogen (H-)tautomerization, that is, a reaction that involves simple intramolecular proton transfer, has been studied in single phthalocyanine, porphyrin, and porphycene derivatives as a prototypical single molecular conductance switch. Here, by means of low-temperature scanning tunneling microscopy and density functional theory calculations, we report a binary H-tautomerism and stereoisomeric conformational switch in (amino-functionalized) porphyrins assembled in molecular chains on a gold surface. We show that the formation of the chain is crucial for the binary tautomeric switch mechanism as the single molecule switches differently. Our findings suggest that the (amino-)functionalization of molecules can be exploited not only to drive the formation of molecular self-assemblies but also to steer their switching properties.
- Published
- 2020