Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings
Abstract: We describe a new type of nitrogen‐centered polycyclic scaffold comprising a unique combination of 5‐, 6‐, and 7‐membered rings. The compound is accessible through an intramolecular oxidative cyclodehydrogenation of tri (1‐naphthyl) amine. To the best of our knowledge this is the very first example of a direct 3‐fold cyclization of a triarylamine under oxidative conditions. The unusual ring fusion motif is confirmed by X‐ray crystallography and the impact of cyclization on the electronic and photophysical properties is investigated both experimentally and theoretically based on density‐functional theory (DFT) calculations. The formation of the unexpected product is rationalized by detailed mechanistic studies on the DFT level. The results suggest the cyclization to occur under kinetic control via a dicationic mechanism.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings ; day:24 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie ; (24.08.2022) (gesamt 1)
- Creator
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Nebauer, Johannes
Neiß, Christian
Krug, Marcel
Vogel, Alexander
Fehn, Dominik
Ozaki, Shuhei
Rominger, Frank
Meyer, Karsten
Kamada, Kenji
Guldi, Dirk M.
Görling, Andreas
Kivala, Milan
- DOI
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10.1002/ange.202205287
- URN
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urn:nbn:de:101:1-2022082515045823690908
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:30 AM CEST
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Associated
- Nebauer, Johannes
- Neiß, Christian
- Krug, Marcel
- Vogel, Alexander
- Fehn, Dominik
- Ozaki, Shuhei
- Rominger, Frank
- Meyer, Karsten
- Kamada, Kenji
- Guldi, Dirk M.
- Görling, Andreas
- Kivala, Milan
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Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings
Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings
Electronic Interplay between Porphyrinoids and Push-Pull Chromophores
Photophysical investigations of pentacene dimers and beyond: Elucidating the mechanism of the singlet fission process
Self-Assembling Monolayers as Contamination Protection Evaluation of Adsorbed Alkylamine Films from ODACON F Emulsion
Shadow Corrosion Phenomenon – An out-of-pile Study on Electrochemical Effects
The Role of Fullerenes in the Photo-degradation of Organic Solar Cells
Comprehensive Photophysical Characterization of Advanced Hexa-peri-hexabenzocoronene and Carbon Nanodot Systems
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Tunable optical properties of mixed self-assembled monolayers on metal oxide nanoparticles
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Quantitative Transduction of Excited-State Energy inFluorophore-Heterofullerene Conjugates
Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings
Oxidative Cyclodehydrogenation of Trinaphthylamine: Selective Formation of a Nitrogen‐Centered Polycyclic π‐System Comprising 5‐ and 7‐Membered Rings
Electronic Interplay between Porphyrinoids and Push-Pull Chromophores
Photophysical investigations of pentacene dimers and beyond: Elucidating the mechanism of the singlet fission process
Self-Assembling Monolayers as Contamination Protection Evaluation of Adsorbed Alkylamine Films from ODACON F Emulsion
Shadow Corrosion Phenomenon – An out-of-pile Study on Electrochemical Effects
The Role of Fullerenes in the Photo-degradation of Organic Solar Cells
Comprehensive Photophysical Characterization of Advanced Hexa-peri-hexabenzocoronene and Carbon Nanodot Systems
Photon- and Charge Management in Advanced Molecular Multicomponent Covalent/Non-Covalent Ensembles
Tunable optical properties of mixed self-assembled monolayers on metal oxide nanoparticles
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