Premium
Synthesis, Photophysical and Electronic Properties of Mono‐, Di‐, and Tri‐Amino‐Substituted Ortho‐Perylenes, and Comparison to the Tetra‐Substituted Derivative
Author(s) -
Merz Julia,
Dietrich Lena,
Nitsch Jörn,
Krummenacher Ivo,
Braunschweig Holger,
Moos Michael,
Mims David,
Lambert Christoph,
Marder Todd B.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001475
Subject(s) - perylene , moiety , chemistry , tetra , photochemistry , excited state , amine gas treating , phosphorescence , derivative (finance) , molecule , fluorescence , stereochemistry , medicinal chemistry , organic chemistry , physics , quantum mechanics , nuclear physics , financial economics , economics
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.