meso-Aryl tribenzosubporphyrin—a totally substituted subporphyrin species

Abstract

meso-Aryl tribenzosubporphyrin was synthesized by a self-condensation of 3-benzalphthalimidine and by a condensation of phthalimide with phenylacetic acid using boric acid as a template; the compounds derived were characterized based on a wide range of spectroscopic and electrochemical methods.

Comparative electronic structures and UV–vis spectra of tribenzosubporphyrin, tribenzomonoazasubporphyrin, tribenzodiazasubporphyrin, and subphthalocyanine: Insight from DFT and TDDFT calculations

“…In 2006, the analogues of subphthalocyanines in which all meso-nitrogen atoms were substituted with the sp 2 -hybrid carbons, the tribenzosubporphyrines [30], were synthesized and characterized as their boron complexes. Later, the meso-phenyl tribenzosubporphyrins were also reported by Luk'yanets, Kobayashi and co-workers [31]. Tribenzosubporphyrins also exhibit intense fluorescence, strong UV-vis absorption, and the similar to subphthalocyanine bowl-shaped geometry.…”

Synthesis of Meso‐Substituted Subphthalocyanine–Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins

“…The selection of a boronate ester template leads to control over the apical substituent (13,(15)(16)(17). Most significant, however, is the ability to engineer the new "meso" substituents at willsynthetic control that makes this new class of hybrid structures uniquely attractive.…”

“…[7] The optical properties of SubPcs are distinctive as they show intense absorption and emission around 550 nm, leading to a particular focus on their application as components in photovoltaic cells. [7,[11][12][13] A small number of subporphyrins are also known, the most notable examples being the synthetic breakthroughs reported by Osuka and Kobayashi leading to the first syntheses of boron tribenzosubporphyrins 5 [14] and 6 [15] ( Figure 2). The most challenging core modification of the oligopyrrole/indole macrocycles is arguably the generation of hybrid structures [16] that lie between the classic porphyrin and phthalocyanine parent structures.…”

Fluorescent Boron Complexes of 25‐Oxa­smaragdyrins Containing Axial Silyloxy Groups

“…In continuation of our studies on B III complexes of meso ‐triaryl 25‐oxasmaragdyrins,2 here we describe the synthesis, structures and properties of the first examples of compounds 5 and 6 (Scheme ), fluorescent B III complexes of meso ‐triaryl 25‐oxasmaragdyrins containing rare silyloxy groups as axial ligands. Torres et al20 and Kobayashi et al21 synthesized B III complexes of subphthalocyanines/subporphyrins containing axial silyloxy groups and explored their properties. To the best of our knowledge, except for the reports on B III subphthalocyanines/subporphyrins20,21 containing axial silyloxy groups, there is no other available report on B III porphyrins/corroles/expanded porphyrinoids containing axial silyloxy groups.…”

“…Torres et al20 and Kobayashi et al21 synthesized B III complexes of subphthalocyanines/subporphyrins containing axial silyloxy groups and explored their properties. To the best of our knowledge, except for the reports on B III subphthalocyanines/subporphyrins20,21 containing axial silyloxy groups, there is no other available report on B III porphyrins/corroles/expanded porphyrinoids containing axial silyloxy groups. Compounds 5 and 6 were prepared in high yields by treating B(OH) 2 complexes of meso ‐triaryl 25‐oxasmaragdyrins such as 3a or 3b with different alkyl/aryl chlorosilanes under mild reaction conditions.…”