Design and synthesis of color-switchable RGB dye

ORGN 757

Taichi Ikeda, ikeda@chem.ucla.edu1, Amar Flood, aflood@indiana.edu2, Weiqiao Deng3, Adides Williams1, W. A. Goddard III4, 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 Simulation Center, California Institute of Technology, Pasadena, CA 91125, (4) Materials and Process Simulations Center, California Institute of Technology, Beckman Institute (139-74), Pasadena, CA 91125
The concept of an electronic paper display (E-PAD), a reflective display that feels like a document printed on conventional paper, emerged in the late 90s. In order to realize a color E-PAD, three different pixels (Red, Green, and Blue) must be arranged on the surface, which makes it difficult to realize the low-cost, easy-to-make color E-PAD. Thus, we have proposed a new concept for the simple design color E-PAD using “RGB dye” impregnated polymer matrix. The RGB dye is defined as a dye that enables to show red green and blue (RGB) colors depending on the applied voltage (Box A).

To realize an RGB dye, we designed a [2]catenane (Box B) consisting of a large macrocycle having three stations interlocked with the cyclobis(paraquat-p-phenylene) (CBPQT4+). The color of the molecule depends on the charge transfer between each station and CBPQT4+. A DFT calculation has suggested that 1,5-dioxynaphthalene (NP), tetrathiafulvalene (TTF), and 2,2'-difluorinated benzidine (F2BZ) would be the best combination to generate RGB colors (Final Model).2 Towards the RGB dye, we started from the synthesis of simple [2]catenanes with three stations NP, TTF and benzidine (BZ) (First and Second Models). The structures of the [2]catenanes were confirmed by ESI-MS and 1H NMR spectroscopy. We have analyzed the electrochemical behavior and color change of these three stations [2]catenanes by spectro-electrochemistry. All aspects of this research will be presented at the poster.