Azulene-Based Organic Cages Formed with 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene: Synthesis and Physicochemical Properties
Abstract A novel [2+3] imine cage, derived from 1,3-diformylazulene and 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene, was synthesized and characterized. NMR spectroscopy and single crystal X-ray diffraction confirmed the formation of a symmetric hexaimine structure. The cage exhibits fluorescence, as well as characteristic azulene redox behavior. However, its stability in solution is sensitive to the acidity of the solvent. Reduction with NaBH4 led to the isolation of a more stable hexaamine cage, providing a means to further stabilize the structure.
Authors
- Marius Andruh (ORCID: https://orcid.org/0000-0001-8224-4866)
- Cristian Enache (ORCID: https://orcid.org/0000-0002-7370-7942)
- Simona Nica (ORCID: https://orcid.org/0000-0001-5666-9043)
- Cătălin Maxim (ORCID: https://orcid.org/0000-0001-6033-3710)
- Andreea Dogaru (ORCID: https://orcid.org/0000-0001-9993-6949)
- Adrian Ion (ORCID: https://orcid.org/0009-0005-5582-3551)
- Anamaria Hanganu (ORCID: https://orcid.org/0000-0002-0433-752X)
Institutions
- University of Bucharest (RO)
- State Phytosanitary Administration (CZ)
- Institute of Organic Chemistry (HU)
- Romanian Academy (RO)
Publication Details
- Journal
- Synthesis
- Published
- 2025-04-23
- DOI
- https://doi.org/10.1055/a-2593-4590
- Primary Topic
- Chemical Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Unitatea Executiva pentru Finantarea Invatamantului Superior, a Cercetarii, Dezvoltarii si Inovarii