Calix[4]arene-Functionalized Naphthalene and Perylene Imide Dyes

Calix[4]arenes bearing one, two, or four 1,8-naphthyl imide groups at the wide rim and bis-calix[4]arenes connected via perylene-bisimide dye spacers have been synthesized. The low-temperature NMR spectrum of the tetranaphthylimide suggests, in agreement with a crystal structure, a C 2-symmetrical pinched cone conformation stabilized via face-to-face π−π interactions between opposite naphthylimide groups. UV−vis and fluorescence studies have been carried out for the perylene bis-calix[4]arene dyes.