C_3v (Trimethyl) p‐(Benzyloxy)calix[6]arene: A Versatile Platform for the Synthesis of Functionalized C_3v Calix[6]arenes

Abstract

Partial methylation of p-(benzyloxy)calix [6]arene leads to the corresponding trimethylated C 3v derivative. This compound was used for the synthesis of new functional calixarenes. The presence of the p-(benzyloxy) substituent allows this new C 3v

A New, Simple and Versatile Strategy for the Synthesis of Short Segments of Zigzag‐Type Carbon Nanotubes

“…Regarding the synthesis of 9 (Figure ), the key cone‐locked decabromo derivative scaffold 8 was obtained by direct alkylation of the starting p ‐(benzyloxy)calix[5]arene in acetonitrile. The presence of the cone conformer was demonstrated by both 1 H NMR spectroscopy experiments (Figure S5 in the Supporting Information) and single‐crystal XRD analysis (Figure and Figures S5a and S19 in the Supporting Information).…”

“…Regarding the synthesis of the calix[6]arene‐derived SWCNT short segment 15 , (Figure ), the synthesis of the dodecabrominated scaffold 14 was more complex than the two previous cases. Indeed, locking the starting p ‐(benzyloxy)calix[6]arene 10 in the cone conformation requires the two‐step pre‐ organisation sequence depicted in Figure . Compound 10 was first alkylated by triethyleneglycol bis(tosylate) (step a in Figure ), and then by methyl iodide (step b in Figure ).…”

p‐(Benzyloxy)calix[8]arene Synthesis Revisited: p‐(Benzyloxy)calix[4]‐, p‐(Benzyloxy)calix[5]‐, p‐(Benzyloxy)calix[7]‐, and p‐(Benzyloxy)bis(homooxa)calix[4]arenes

“…The ease of removal of the benzyl groups under mild hydrogenolysis conditions, along with the possibility to easily convert these derivatives into calixquinones [51] opens very interesting perspectives for the formation of new ligands, easily derivatized at the pposition.…”

“…The results reported here (along with previous ones [7,16,21,42] ) clearly demonstrate the potential of p-(benzyloxy)phenol for calixarene synthesis. The ease of removal of the benzyl groups under mild hydrogenolysis conditions, along with the possibility to easily convert these derivatives into calixquinones [51] opens very interesting perspectives for the formation of new ligands, easily derivatized at the pposition.…”

Functionalization reactions of calixarenes

“…Some examples of functionalization of the calixarene narrow rim, selected from a large number of such processes, [96][97][98][99][100][101] are presented. For the functionalization of calixarene narrow rim using Pdcatalyzed Sonogashira coupling reactions, the bis-triflate calixarene 76 and alkynes 77a-d have been employed.…”