Tetraaryltetraanthra[2,3]porphyrins: Synthesis, Structure, and Optical Properties

Abstract

A synthetic route to symmetrical tetraaryltetraanthra[2,3]porphyrins (Ar(4)TAPs) was developed. Ar(4)TAPs bearing various substituents in meso-phenyls and anthracene residues were prepared from the corresponding pyrrolic precursors. The synthesized porphyrins possess high solubility and exhibit remarkably strong absorption bands in the near-infrared region (790-950 nm). The scope of the method, selection of the peripheral substituents, choice of the metal, and their influence on the optical properties are discussed together with the first X-ray crystallographic data for anthraporphyrin.

Reversible oxygen addition on a triplet sensitizer molecule: protection from excited state depopulation

“…In our recent work on the synthesis of tetraanthraporphyrins 17 we observed a photoactivated addition of up to four oxygen molecules per porphyrin molecule, leading to the formation of corresponding endoperoxides. We proposed that such an addition can serve as a tool for preventing oxygen from quenching of porphyrin phosphorescence.…”

Studying the intersystem crossing rate and triplet quantum yield of meso-substituted porphyrins by means of pulse train fluorescence technique

“…The remarkable optical properties of porphyrins continue to attract significant attention, mainly due to their large excited state absorption [1,2] (particularly in the near-IR part of the spectrum [3]), two-photon absorption [4,5], fast intersystem crossing (ISC) [6], excellent optical stability and biocompatibility [7]. As a result of these features porphyrins have extensively been studied with respect to the development of novel optoelectronic and photonic devices [8].…”

Upconverting the IR-A Range of the Sun Spectrum using Palladium Tetraaryltetraanthra[2,3]porphyrins

“…20 Typical procedure for the metallation of free base TAP: Synthesis of free-base TAP porphyrins was performed as previously described.…”

“…17 Despite perspective properties of TAP-rubrene system, particularly its reasonable efficiency (quantum yield of ~ 1% demonstrated) further ivestigation of TAPs as sensitizers has been terminated by their availability. 20 Based on this synthetic work TAPs with various substitution pattern became available as regular sensitizers for TTA-UC. The first representative of the TAP family was reported by Kobayashi and co-workers.…”