COMPLEXATION OF AROMATIC MOLECULES WITH NEW CALIXARENE DERIVATIVES CONTAINING TWO ARYL SULFIDE RINGS
The cuplike structure of calix[4]arenes is one of the most attractive features, which has been observed both in the solid state and in solution. The newly synthesized 5,11,17,23-tetrakis(3-mercaptopropyl)calix[4]arene (1) and 25,26,27,28-tetrakis(5-mercaptopenthoxy)calix[4]arene containing aryl sulfide rings (2), have four alkyl thiol linkages, which allow the calixarenes to attach onto the gold surface. Surface plasmon resonance (SPR) spectroscopy allows us to monitor the binding of calixarene derivatives on the gold surface. The 1 and 2 bind very effectively on the gold surface and self-assembled layers of 1 and 2 produce significant change in SPR signals in 30 min. Calixarenes layers are used as platforms for molecular recognition, where complementary binding sites are easily and selectively introduced. The aromatic molecules used in this study are anthracene, pyrene, coronene and rubrene. The host-guest properties of these aromatic molecules and the calixarene cavity exhibit selectivity of these aromatic molecules. The anthracene, pyrene and coronene have moderate binding affinity to the cavity, and the rubrene does not bind at all.