Carbazole based donor-acceptor compounds: Highly fluorescent organic nanoparticles

ORGN 568

Sujeewa S. Palayangoda, palayas@bgsu.edu, Xichen Cai, xichenc@bgsu.edu, Ravi M. Adhikari, ravia@bgsu.edu, and Douglas C. Neckers, neckers@photo.bgsu.edu. Center for Photochemical Sciences, Bowling Green State University, 141 Overman Hall, Bowling Green, OH 43403
Highly fluorescent and stable carbazole based donor-acceptor compounds 1,2-dicyano-trans-1,2-bis-4(carbazolyl)phenylethylene (1) and 1,2-dicyano-trans-1,2-bis-4(3,6-di-t-butylcarbazolyl)phenylethylene (2) are synthesized and characterized. They show negative solvatochromic absorption behavior, but show both positive and negative solvatochromic behavior in the fluorescence spectra. They also show very high solid state quantum yields of emission (0.72 and 0.88). In water/THF mixture, 1 as well as 2 aggregate into 50-150 nm nanoparticles and the emission quantum yield of 1 and 2 nanoparticles is much higher than that of 1 and 2 in solution.