title: Nanoscopic imaging of meso-tetraalkylporphyrins prepared in high yields enabled by Montmorrilonite K10 and 3A molecular sieves.
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.
authors.affiliation: Aix Marseille Université, CNRS UMR 7313, Institut des Sciences Moléculaires de Marseille (iSm2), Chirosciences, Avenue Escadrille Normandie Niemen, St. Jerôme, 13397 Marseille CEDEX 20, France.
authors.forename: Rémi
authors.initials: R
authors.lastname: Plamont
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Kikkawa
authors.forename: Mayuko
authors.initials: M
authors.lastname: Takahashi
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kanesato
authors.forename: Michel
authors.initials: M
authors.lastname: Giorgi
authors.forename: Anita
authors.initials: A
authors.lastname: Chan Kam Shun
authors.forename: Christian
authors.initials: C
authors.lastname: Roussel
authors.forename: Teodor Silviu
authors.initials: TS
authors.lastname: Balaban
keywords: clays; graphite; interfaces; porphyrinoids; self-assembly