Nanoscopic Imaging of meso‐Tetraalkylporphyrins Prepared in High Yields Enabled by Montmorrilonite K10 and 3 Å Molecular Sieves. Issue 34 (9th July 2013)

• Record Type: Journal Article
• Authors: Plamont, Rémi; Kikkawa, Yoshihiro; Takahashi, Mayuko; Kanesato, Masatoshi; Giorgi, Michel; Chan Kam Shun, Anita; Roussel, Christian; Balaban, Teodor Silviu
• Is Part Of: Chemistry. Volume 19:Issue 34(2013)
• Page Start: 11293
• Page End: 11300
• Publication Date: 2013-07-09
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201300532
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>We have developed a high‐yielding synthesis of <italic>meso</italic>‐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 (<bold>C10</bold>) 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 <bold>C13</bold> to <bold>C16</bold>. For <bold>C13</bold> a single‐crystal X‐ray structure allowed an unprecedented insight into how packing from two dimensions is expanded into a three‐dimensional crystal lattice.</p> </abstract>