Synthesis, Structure, and Anion Binding Properties of Electron‐Deficient Tetrahomocorona[4]arenes: Shape Selectivity in Anion–π Interactions

• Published in: Angewandte Chemie Vol. 130; no. 22; pp. 6646 - 6650
• Main Authors: Liu, Han‐Bin, Zhang, Qian, Wang, Mei‐Xiang
• Format: Journal Article
• Language: English
• Published: 28.05.2018
• Subjects: Anion-π-Wechselwirkungen; Anionenerkennung; Coronarene; Makrocyclen; Thiocyanat
• ISSN: 0044-8249; 1521-3757
• DOI: 10.1002/ange.201802650

Tetrahomocorona[2]arene[2]tetrazines were constructed by means of a fragment coupling strategy based on nucleophilic aromatic substitution reaction starting from 3,6‐dichlorotetrazine and o‐, m‐, and p‐bis(hydroxymethyl)benzenes. The unprecedented macrocycles gave rectangular box‐like cavities with tunable cavity sizes and deficient electronic properties depending on the substitution pattern of phenylene. Due to anion–π interactions, they formed complexes selectively with azide and thiocyanate owing to complementary shapes between host and guest. Passt! Tetrahomocorona[2]aren‐[2]Tetrazine, die elektronenarme rechteckige Hohlräume mit einstellbarer Größe enthalten, bilden selektiv Komplexe mit Azid und Thiocyanat. Die Selektivität geht auf die komplementären Formen zwischen Wirt und Gast bei der Bildung der Anion‐π‐Wechselwirkungen zurück.