N-Annulated Perylene Fused Porphyrins with Enhanced Near-IR Absorption and Emission

Abstract

N-Annulated perylene fused porphyrins 1 and 2 were synthesized by oxidative dehydrogenation using a Sc(OTf)(3)/DDQ system. These newly synthesized hybrid molecules are highly soluble in organic solvents and exhibit remarkably intense near-IR absorption, as well as detectable photoluminescence quantum yields, all of which are comparable to or even exceed those of either meso-β doubly linked porphyrin dimer/trimer or bis/tri-N-annulated rylenes.

Porphyrin Donor and Tunable Push–Pull Acceptor Conjugates—Experimental Investigation of Marcus Theory

“…Halogen–lithium exchange and quenching with molecular iodine provided the corresponding iodide 13 . The previously reported phenylacetylene‐ and pinacolborane‐substituted porphyrins 14 and 15 could then be coupled with aryl halides 13 or 12 to give 16 and 17 , respectively. Aldehyde 18 , the synthesis of which is outlined in Section S2 of the Supporting Information, could be used to form porphyrin 19 , whereby the aliphatic portion of the linker is bound directly to the porphyrin.…”

Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells

“…This was attempted in some push− pull porphyrins incorporating diketopyrrolopyrrole (DPP), 290 BODIPY 291 subunits, or another porphyrin (dimer 128 or triad 129 Figure 56). 292,293 In conjunction with the electrolyte based on the Co III/II tris(2,2′-bipyrine) complex, [Co(bipy) 3 ] 3+/2+ , the TiO 2 /DSSCs devices made with WW-5 or WW-6 dyes showed impressive photovoltaic performances (Table 31), achieving a PCE of 10.3% and 10.5% respectively, under AMG 1.5 standard conditions, equaling those of YD2-o-C8 under same conditions (η = 10.5%), and were even slightly higher under half-sun illumination (η = 11.1%, 11.3%, and 10.8% under 50 mW·cm −2 irradiance, respectively). Various factors were considered for the design of these dyes.…”

Reoxidation of Transition‐metal Catalysts with O2

“…In the early stage, we disclosed a novel Cu-catalyzed aerobic oxidative amidation of propiolic acids under air as the first intermolecular C(sp)-X bond formation via decarboxylation. [22] The use of propiolic acid derivatives, which are readily available, easy to store, and simple to handle, as the coupling partner efficiently inhibits the formation of dimerization product diynes, as well as reduces the loading of the catalyst and the amide nucleophiles (Scheme 13a).…”