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Nanoscopic Imaging of meso ‐Tetraalkylporphyrins Prepared in High Yields Enabled by Montmorrilonite K10 and 3 Å Molecular Sieves
Author(s) -
Plamont Rémi,
Kikkawa Yoshihiro,
Takahashi Mayuko,
Kanesato Masatoshi,
Giorgi Michel,
Chan Kam Shun Anita,
Roussel Christian,
Balaban Teodor Silviu
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300532
Subject(s) - molecular sieve , nanoscopic scale , highly oriented pyrolytic graphite , pyrolytic carbon , stacking , materials science , chemical engineering , graphite , solvent , catalysis , crystallography , molecule , mesoporous material , nanostructure , crystal (programming language) , nanotechnology , organic chemistry , chemistry , composite material , pyrolysis , computer science , engineering , programming language
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.