Synthesis, Photophysical and Electronic Properties of Mono‐, Di‐, and Tri‐Amino‐Substituted Ortho‐Perylenes, and Comparison to the Tetra‐Substituted Derivative

Please always quote using this URN: urn:nbn:de:bvb:20-opus-217835
  • 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 DPAWe 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.show moreshow less

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Metadaten
Author: Julia Merz, Lena Dietrich, Jörn Nitsch, Ivo Krummenacher, Holger Braunschweig, Michael Moos, David Mims, Christoph Lambert, Todd B. Marder
URN:urn:nbn:de:bvb:20-opus-217835
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Chemistry – A European Journal
Year of Completion:2020
Volume:26
Issue:52
First Page:12050
Last Page:12059
Source:Chemistry – A European Journal 2020, 26(52):12050-12059. DOI: 10.1002/chem.202001475
DOI:https://doi.org/10.1002/chem.202001475
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:borylation; intersystem crossing; luminescence; polycyclic aromatic hydrocarbon; triarylamine
Release Date:2021/07/20
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International