Calix[4]arene-functionalized naphthalene and perylene imide dyes.
[reaction: see text] 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 C2-symmetrical pinched cone conformation stabilized via face-to-face pi-pi interactions between opposite naphthylimide groups. UV-vis and fluorescence studies have been carried out for the perylene bis-calix[4]arene dyes.
Fachbereich Chemie und Pharmazie, Abteilung Lehramt Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, D-55099 Mainz, Germany.
Myroslav O
MO
Vysotsky
Volker
V
Böhmer
Frank
F
Würthner
Chang-Cheng
CC
You
Kari
K
Rissanen
D047250:Calixarenes; D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes; D010569:Perylene; D010636:Phenols / Q000737:chemistry
D004396:Coloring Agents; D005456:Fluorescent Dyes; D007094:Imides; D009281:Naphthalenes; D010636:Phenols; C121325:calix(4)arene; D047250:Calixarenes; C031721:naphthalene; D010569:Perylene