Azulene-Based Organic Cages Formed with 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene: Synthesis and Physicochemical Properties

Adrian E. Ion; Andreea Dogaru; Catalin Maxim; Anamaria Hanganu; Cristian Enache; Marius Andruh; Simona Nica

doi:10.1055/a-2593-4590

Synthesis, Table of Contents

Synthesis 2025; 57(14): 2189-2196
DOI: 10.1055/a-2593-4590

paper

Romanian Chemists in Synthesis

Azulene-Based Organic Cages Formed with 1,3,5-Tris(aminomethyl)-2,4,6-triethylbenzene: Synthesis and Physicochemical Properties

Adrian E. Ion

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

,

Andreea Dogaru

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

,

Catalin Maxim

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

^bFaculty of Chemistry, University of Bucharest, Regina Elisabeta Blvd. 4–12, 030018 Bucharest, Romania

,

Anamaria Hanganu

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

^bFaculty of Chemistry, University of Bucharest, Regina Elisabeta Blvd. 4–12, 030018 Bucharest, Romania

,

Cristian Enache

^cNational Phytosanitary Authority of Agriculture Ministery, Blvd. Voluntari 11, 077190 Voluntari, Ilfov, Romania

,

Marius Andruh∗

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

^bFaculty of Chemistry, University of Bucharest, Regina Elisabeta Blvd. 4–12, 030018 Bucharest, Romania

,

Simona Nica∗

^aC. D. Nenitzescu Institute of Organic and Supramolecular Chemistry, Splaiul Independentei 202B, 060023 Bucharest, Romania

› Author Affiliations

Abstract

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This paper is dedicated to the memory of Professor Ovidiu Maior, an example of scientific excellence and mentorship.

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.

Key words

azulene-based cages - Schiff base - fluorescence - redox active - hexaamine macrocycle

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References

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Supplementary Material

Supporting Information