Tetra- and Octapyrroles Synthesized from Confusion and Fusion Approaches

Abstract

By oxidation of an alternately N-confused bilane in CH 2 Cl 2 , a C−N fused tetrapyrrin was synthesized that bears a 5.5.5-tricyclic ring generated from an intramolecular C−N linkage. When CH 3 CN was used as the reaction medium, a multiply C−N-fused octapyrrolic dimer was also obtained that contained two 5.5.5.7.5-pentacyclic moieties and a bipyrrole unit generated from the intramolecular C−N linkage and intermolecular C−C linkage, respectively. This could be coordinated with Ni(acac) 2 to afford a mixed-ligand complex.

Rational Synthesis of 5,5,5‐Tricyclic Fused Thia‐heptaphyrin (1.1.1.1.1.1.0) From a Helical Oligopyrrin Hybrid

“…For instance, singly/doubly N‐fused porphyrins, fused heptaphyrins/hexaphyrins have been reported . In our previous work, unique tetra‐ and octapyrrins were synthesized by combining the confusion and fusion approaches . Subsequent trials on synthesizing the corresponding porphyrinoids through oxidative ring closure reactions failed, presumably due to the inappropriate distances between the terminal pyrrole units of the tetra‐ and octapyrrins.…”

Sterically Protected N2O-Type Benzopyrromethene Boron Complexes from Boronic Acids with Intense Red/Near-Infrared Fluorescence

“…Fluorescent dyes have found diverse applications in medical and material sciences, including noninvasive bioimaging, molecular sensing, photothermal therapy, photovoltaic, and optoelectronics . Stable tetracoordinated organoboron complexes as potential functional fluorescent dyes have recently received much attention since boron complexation can rigidify molecules and thus generate or enhance fluorescence.…”

Stable 5,5′-Substituted 2,2′-Bipyrroles: Building Blocks for Macrocyclic and Materials Chemistry

“…The successful preparation of such a quaterpyrrole prompted us to generalize this synthetic methodology, giving a straightforward access to substituted bipyrroles 3 bearing aromatic and unsaturated moieties at positions 5,5′ (Scheme ). The conjugated structure and the presence of the bipyrrolic moiety make these new molecules of interest in the design of metal ligands, − macrocyclic receptors, ,,− molecular electronics, light-emitting diodes, electrochromic devices, molecular wires, the preparation of conjugated low band gap polymers, − and polymer-based sensors. − …”