Nanoscopic Imaging of meso‐Tetraalkylporphyrins Prepared in High Yields Enabled by Montmorrilonite K10 and 3 Å Molecular Sieves

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Abstract
We have developed a high‐yielding synthesis of meso‐tetraalkylporphyrins, which previously have been obtained only in lower yields. By employing Montmorrilonite K10 as the acid catalyst and 3 Å molecular sieves as the dehydrating agent, yields that reached 70 % could be achieved with some aliphatic aldehydes. The free‐base porphyrins with decyl (C10) or longer chains were imaged at the single‐molecule level at the solvent/surface interface. Highly oriented pyrolytic graphite (HOPG) was used as a π‐stacking surface, whereas 1‐phenyloctane and 1‐phenylnonane were used as solvents. An odd–even effect was observed from C13 to C16. For C13 a single‐crystal X‐ray structure allowed an unprecedented insight into how packing from two dimensions is expanded into a three‐dimensional crystal lattice.
Funding Information
  • Sumitomo Foundation
  • JSPS (23750137)
  • MEXT KAKENHI, Japan (23106722)
  • FP7 Future and Emerging Technologies Programme

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