Synthesis of a Calix[4]semitube with a Selectively Dinitrated Face

This paper describes the synthesis and characterisation of the calix semitube 5. The calix[4]semitube consists of two calix[4]arenes connected through their lower rim from two phenol groups in distal positions. One calix[4]arene is unsubstituted on its upper rim, while the upper rim of the other calix[4]arene has two nitro groups in the 1,3- position and two tert-butyl groups in the remaining ones. The synthesis procedure yielded an amorphous structure, which did not provide a single crystal. The final compound was comprehensively characterised by infrared spectroscopy, mass spectrometry, and ¹H and ¹³C NMR spectroscopy. The results of the ¹H NMR spectroscopy confirmed that the calix[4]arene units adopted a cone conformation. This was confirmed by COSY and ¹H-¹³C HMBC. The results obtained confirm that the compound was successfully synthesised. The IUPAC name of 5 is 2,34-di-tert-butyl-39,49-dinitro-6,7,8,9,27,28,29,30-octahydro-15H,21H,36H,42H-4,32:11,25-bis(methano [1,3]benzenomethano)-16,20:37,41-di(metheno)tetrabenzo[g,g1,p,x][1,6,18,23] tetraoxacyclotetratriacontine-43,46,54,60-tetraol.