Synthesis and Supramolecular Properties of a Novel Octaphosphonate Porphyrin

Abstract

Two complementary routes were developed for preparing novel octaphosphonate porphyrins. The use of protected/deprotected phosphonate-substituted precursors in the rational synthesis gave an overall yield 16 %. A more streamlined synthetic path gave 21 % overall yield of the target molecule. Octaphosphonate porphyrin possesses promising properties in supramolecular aggregate formation with cyclam. Cofacial reversible self-assembly of a meso-substituted octaphos-

RETRACTED: pH Dependent Molecular Self-Assembly of Octaphosphonate Porphyrin of Nanoscale Dimensions: Nanosphere and Nanorod Aggregates

“…However, studies along these lines are still limited [ 4 , 5 ]. Nevertheless, in our earlier work, we have demonstrated synthesis of novel octaphosphanatoporphyrin (OctaPhosPor) 1 [ 20 ], and its cofacial reversible self-assembly with cyclam, which yields micrometer long monomolecular nanowires. We speculated that self-assembly was modulated by intermolecular hydrogen bonding of the amino groups of cyclam with phosphonato moieties of 1 .…”

Phosphonate-Derivatized Porphyrins for Photoelectrochemical Applications

“…Synthesis of meso-substituted porphyrins was carried out by acid-catalyzed condensation reactions following procedures developed by Lindsey et al , The synthetic route to the porphyrins is shown in Scheme . Compounds 7 , 8 , 9 , 10 , and 11 (Scheme ; Scheme S1, SI) were synthesized by literature procedures. Compound 12 was reported earlier.…”

“…Synthesis of meso-substituted porphyrins was carried out by acid-catalyzed condensation reactions following procedures developed by Lindsey et al 17,18 The synthetic route to the porphyrins is shown in Scheme 1. Compounds 7, 19 8, 20 9, 21 23 5-(Heptafluoropropyl)dipyrrylmethane (12). 2,2,3,3,4,4,4-Heptafluorobutanal (4g, 20.2 mmol) was dissolved in THF (60 mL), and the solution was degassed by argon bubbling for 20 min.…”

Melamine and Spermine Mediated Supramolecular self–assembly of Octaphosphonate Tetraphenyl Porphyrin

“…[17][18][19][20][21][22] In recent years, we have undertaken work based on {porphyrin-5,10,15,20-tetrayltetrakis[(benzene-5,1,3-triyl)bis (methylene)]}octakis(phosphonic acid) 1 and reported several findings on nanostructure syntheses using this material such as nanowires, nanorods, spherical aggregates and chiral supramolecular nanostructures using a bottom-up approach based on supramolecular self-assembly. [23][24][25]…”