Base‐Assisted Imidization: A Synthetic Method for the Introduction of Bulky Imide Substituents to Control Packing and Optical Properties of Naphthalene and Perylene Imides

Please always quote using this URN: urn:nbn:de:bvb:20-opus-218246
  • We report the direct imidization of naphthalene and perylene dicarboxylic anhydrides/esters with bulky ortho,ortho‐diaryl‐ and ortho,ortho‐dialkynylaniline derivatives. This imidization method uses n‐butyllithium as a strong base to increase the reactivity of bulky amine derivatives, proceeds under mild reaction conditions, requires only stoichiometric amounts of reactants and gives straightforward access to new sterically crowded rylene dicarboximides. Mechanistic investigations suggest an isoimide as intermediary product, which was convertedWe report the direct imidization of naphthalene and perylene dicarboxylic anhydrides/esters with bulky ortho,ortho‐diaryl‐ and ortho,ortho‐dialkynylaniline derivatives. This imidization method uses n‐butyllithium as a strong base to increase the reactivity of bulky amine derivatives, proceeds under mild reaction conditions, requires only stoichiometric amounts of reactants and gives straightforward access to new sterically crowded rylene dicarboximides. Mechanistic investigations suggest an isoimide as intermediary product, which was converted to the corresponding imide upon addition of an aqueous base. Single‐crystal X‐ray diffraction analyses reveal dimeric packing motifs for monoimides, while two‐side shielded bisimides crystallize in isolated molecules without close π–π‐interactions. Spectroscopic investigations disclose the influence of the bulky substituents on the optical properties in the solid state.show moreshow less

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Metadaten
Author: Magnus Mahl, Kazutaka Shoyama, Ana‐Maria Krause, David Schmidt, Frank WürthnerORCiDGND
URN:urn:nbn:de:bvb:20-opus-218246
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Angewandte Chemie International Edition
Year of Completion:2020
Volume:59
Issue:32
First Page:13401
Last Page:13405
Source:Angewandte Chemie International Edition 2020, 59(32):13401–13405. DOI: 10.1002/anie.202004965
DOI:https://doi.org/10.1002/anie.202004965
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:dyes; fluorescence; imidization; perylene imide; solid-state emitters
Release Date:2021/08/20
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International