Anion-π Interactions in Direct Amination of Core-Unsubstituted Perylene Monoimides
Gültekin D.D. Acar M. Hanım Emanet N. Aydogdu S. Hatipoglu A. Myltykbayeva Z. Koca A. Kazaz C. Fidan M. Bozdemir Ö.A.
2026John Wiley and Sons Inc
Chemistry - A European Journal
2026
The incorporation of amino substituents at the peri-positions of perylene monoimides (PMIs) produces elusive push-pull systems with absorption and emission properties in the UV–vis and Near-IR regions. We describe a survey of different direct amination methods for the one-step synthesis of a series of 9-alkylamino and 9-arylamino PMIs. The first method tested is direct amination in neat amines and succesfull only for pyrrolidine. The second method uses the PCC/AgNO3 oxidant system, and high yields are obtained with pyrrolidine. The third method employs KMnO4/AgNO3 as a stronger oxidant system. Pyrrolidine and piperidine are favorable amines for this method, and even diamino PMIs can be obtained. The fourth method uses a Cu(II) salt as a catalyst, and cyclic amines afford products in high yields. The final method is the anion-mediated direct amination and provides the most suitable method for a variety of cyclic, alkyl, and aryl amines to give 9-alkylamino and 9-arylamino PMIs in high yields. In this method, TBAF or TBAOH is used as the anion source, and our detailed spectroscopic and synthetic studies reveal that, as a result of single-electron transfer from the anion, PMIs can generate radical anions and participate in a radical mechanism in amination.
anion-π interactions , direct amination , perylene monoimides , radical anions , rylene imides
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Department of Chemistry and Chemical Process Technologies, Technical Sciences Vocational School, Atatürk University, Erzurum, Turkey
Department of Chemistry, Atatürk University, Erzurum, Turkey
Department of Chemistry, Yildiz Technical University, Istanbul, Turkey
Research Institute of New Chemical Technologies and Materials, Al-Farabi Kazakh National University, Almaty, Kazakhstan
Chemical Engineering Department, Engineering Faculty, Marmara University Recep Tayyip Erdoğan Campus, Istanbul, Turkey
Department of Physics, Atatürk University, Erzurum, Turkey
Department of Chemistry and Chemical Process Technologies
Department of Chemistry
Department of Chemistry
Research Institute of New Chemical Technologies and Materials
Chemical Engineering Department
Department of Physics
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