Abstract
We synthesized a series of new mono‐, di‐, tri‐ and tetra‐substituted perylene derivatives with strong bis(para‐methoxyphenyl)amine (DPA) donors at the uncommon 2,5,8,11‐positions. The properties of our new donor‐substituted perylenes were studied in detail to establish a structure‐property relationship. Interesting trends and unusual properties are observed for this series of new perylene derivatives, such as a decreasing charge transfer (CT) character with increasing number of DPA moieties and individual reversible oxidations for each DPA moiety. Thus, (DPA)‐Per possesses one reversible oxidation while (DPA)4‐Per has four. The mono‐ and di‐substituted derivatives display unusually large Stokes shifts not previously reported for perylenes. Furthermore, transient absorption measurements of the new derivatives reveal an excited state with lifetimes of several hundred microseconds, which sensitizes singlet oxygen with quantum yields of up to 0.83.
Highlights
Perylene diimides (PDIs) are one of the most intensively studied classes of functional organic materials due to their thermal, chemical and photochemical stability.[1,2,3,4,5] Their optical properties are especially interesting as they have quantum yields near unity and exceptional self-assembly behavior
We showed that (DPA)4-Per can sensitize singlet oxygen with a quantum yield of 0.60, which was detected by its luminescence at 1272 nm upon excitation of an O2-saturated toluene solution.[30]
The observed electrochemical behavior is consistent with our calculations, as each derivatives with strong bis(paramethoxyphenyl)amine (DPA) unit adds one orbital close to the HOMO of the respective derivative, so that the ease of removing an additional electron from the system increases with the number of substituents
Summary
Perylene diimides (PDIs) are one of the most intensively studied classes of functional organic materials due to their thermal, chemical and photochemical stability.[1,2,3,4,5] Their optical properties are especially interesting as they have quantum yields near unity and exceptional self-assembly behavior.
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