Phosphorescent perylene imides

Abstract

Asymmetrically substituted perylene imide derivatives PIa and PIx display phosphorescence in glassy matrices at 77 K. The lifetime is 49.0 ms for PIa and 13.5 ms for PIx. The triplet energy is 1.79 eV for PIa and 1.68 eV for PIx as confirmed by sensitization experiments of the C 60 triplet.

Near‐IR Phosphorescent Ruthenium(II) and Iridium(III) Perylene Bisimide Metal Complexes

“…[18] In line with our theoretical studies, we attribute the phosphorescence in 1 to originate from a mixed 3 ML(ab-PBI)/ 3 ILCT state, whereas emission in 2 is 3 IL(ab-PBI) in nature. [7] Introduction of the electron-withdrawing aza-nitrogen in ab-PBI and the Lewis acidic metal fragments in 1 and 2 apparently stabilize the bonding PBI molecular orbitals to a greater extent than the anti-bonding MOs. [19] A similar triplet excited-state energy of 1.68 eV has been found by Flamigni upon attachment of electron withdrawing functional groups at the perylene moiety.…”

“…[5] Many of these applications make use of the energetically lowest singlet excited state (S 1 ) of PBI. [7] However, the phosphorescence spectrum could only be obtained in a 77 K glass matrix by an external heavy atom effect that is mediated by ethyl iodide. One example has been described by Janssen and co-workers, who investigated a cofacially stacked PBI dimer and could demonstrate triplet state formation by singlet oxygen sensitization experiments.…”

Highly Soluble Benzo[ghi]perylenetriimide Derivatives: Stable and Air‐Insensitive Electron Acceptors for Artificial Photosynthesis

“…[18] This value is even higher than that of fullerene systems such as C 60 [ E (T 1 )≈1.63 eV][19] and [60]PCBM [ E (T 1 )≈1.50 eV]. [20] Consequently, in the design of long-lived charge-transfer states,[21] the BPTI chromophore could potentially provide the solution to avoid triplet formation by charge recombination.…”

Photoinduced processes in a dyad made of a linear and an angular perylene bisimide

“…Therefore, at variance with most perylene bisimides, it displays typical triplet state photoreactivity as singlet oxygen photosensitization 8 with ϕ Δ = 0.68 ± 0.02, and low temperature phosphorescence at 692 nm. 9 PIa has also been used as an electron donor in a dyad comprising corrole and has provided a charge separated state lifetime of several microseconds, an impressive result if one considers the simple structure of the array and the close proximity of the reactants. 10 The reason for such behaviour has to be ascribed to a quite high driving force, of the order of 2 eV, together with a very small rearrangement of the molecular structure from the charge separated state to the ground state.…”

“…[7][8][9] This new perylene bisimide derivative is more electron rich than PI0, in addition to a still high fluorescence quantum yield (ϕ fl = 0.37 ± 0.03) PIa is able to undergo efficient intersystem crossing. Therefore, at variance with most perylene bisimides, it displays typical triplet state photoreactivity as singlet oxygen photosensitization 8 with ϕ Δ = 0.68 ± 0.02, and low temperature phosphorescence at 692 nm.…”