Towards a tristable [2]catenane

ORGN 44

Taichi Ikeda, ikeda@chem.ucla.edu1, Amar Flood, aflood@indiana.edu2, Weiqiao Deng3, Sourav Saha1, Ivan Aprahamian1, W. A. Goddard III3, and J. Fraser Stoddart, stoddart@chem.ucla.edu1. (1) California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, (2) Department of Chemistry, Indiana University, Bloomington, IN 47405, (3) Materials and Process Simulations Center, California Institute of Technology, Pasadena, CA 91125
The synthesis and characterization of the electrochemically-controllable two-station [2]catenanes and [2]rotaxanes have been tackled in the last decade or so. These studies have led to the attractive applications such as molecular switches, memories and linear molecular motors. The synthesis of the tristable three-station [2]catenanes and [2]rotaxanes could expand the possibility of the device applications. For instance, we have proposed an electrochemically-controllable RGB (Red/Green/Blue) [2]catenane (Box A), in which the color of the compound can be changed in relation to the location of the cyclobis(paraquat-p-phenylene) (CBPQT4+) on the crown ether with three stations. At first, we established the synthetic route to the three-station [2]catenane consisting of the CBPQT4+ and crown ether with three stations [tetrathiafulvalene (TTF), benzidine (BZ) and 1,5-dioxynaphthalene (DNP)] linked by the tetra(ethylene glycol) (First Model). The First Model [2]catenane was found to be a bistable one. Thus, the modified three-station [2]catenane (Second Model) was synthesized by taking into account the association constants (Box B) of each station. Although the Second Model [2]catenane was also found to be bistable one, these experimental results afford us the clue to the design of the electrochemically-controllable tristable [2]catenanes.

 

Materials, Devices, and Switches
8:00 AM-12:00 PM, Sunday, 10 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006