ArticleAngewandte Chemie (International ed. in English)2020
Base-Assisted Imidization: A Synthetic Method for the Introduction of Bulky Imide Substituents to Control Packing and Optical Properties of Naphthalene and Perylene Imides.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Colour by design: tuning the solid-state emission of coronene bisimide by tailored matrices.Chemical science · 2026Article
- Probing Side-Chain Engineering for Modulating Exciton Dynamics in Non‑fullerene Acceptors.ACS omega · 2026Article
- Brightness of fluorescent organic nanomaterials.Chemical Society reviews · 2023Review
- Enantioselective Recognition of Helicenes by a Tailored Chiral Benzo[ghi]perylene Trisimide π-Scaffold.Angewandte Chemie (International ed. in English) · 2022Article
- Multilayer stacks of polycyclic aromatic hydrocarbons.Nature chemistry · 2022Article
- Macrocyclic Donor-Acceptor Dyads Composed of a Perylene Bisimide Dye Surrounded by Oligothiophene Bridges.Angewandte Chemie (International ed. in English) · 2022Article
- Base-Assisted Imidization: A Synthetic Method for the Introduction of Bulky Imide Substituents to Control Packing and Optical Properties of Naphthalene and Perylene Imides.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
5 authors.
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Abstract
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 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.
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