Anthracene-Containing [2]Rotaxanes: Synthesis, Spectroscopic, and Electrochemical Properties

✍ Scribed by Roberto Ballardini; Vincenzo Balzani; Wim Dehaen; Adele E. Dell'Erba; Françisco M. Raymo; J. Fraser Stoddart; Margherita Venturi

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 569 KB
• Volume: 2000
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(200002)2000:4<591::aid-ejoc591>3.0.co;2-i

✦ Synopsis

Two dumbbell-shaped compounds (8 and 11), each composed of two polyether chains intercepted by a 1,4-dioxybenzene recognition site, terminated by tetraarylmethane-based stoppers, and emanating from a central 9,10-or a 2,6-dioxyanthracene unit, have been synthesized. Two [2]rotaxanes (9 ⋅ 4 PF 6 and 12 ⋅ 4 PF 6 ) have been prepared by interlocking these dumbbell-shaped compounds (8 and 11) with a bipyridinium-based tetracationic cyclophane (15 ⋅ 4 PF 6 ) -namely, cyclobis(paraquat-p-phenylene). A [3]rotaxane (10 ⋅ 8 PF 6 ) incorporating two cyclophane components (15 ⋅ 4 PF 6 ) was also obtained when the 9,10-dioxyanthracene-containing dumbbell-shaped compound (8) incorporating two 1,4-dioxybenzene recognition sites was employed. The 1 H-NMR spectroscopic investigation of the [2]rotaxanes (9 ⋅ 4 PF 6 and 12 ⋅ 4PF 6 ) revealed that the cyclophane component encircles