The influence of tetrahydroquinoline rings in dicyanodihydrofuran (DCDHF) fluorophores

ORGN 512

Hui Wang, hwang@kent.edu1, Zhikuan Lu, zlu1@kent.edu1, Robert J. Twieg, rtwieg@lci.kent.edu1, Samuel J. Lord, sjlord@stanford.edu2, and W. E. Moerner, wmoerner@stanford.edu2. (1) Department of Chemistry, Kent State University, Kent State University, Kent, OH 44240, (2) Department of Chemistry, Stanford University, Stanford, CA 94305-5080
We have synthesized several series of DCDHF fluorophores with the amine donor either acyclic or constrained in one or two tetrahydroquinoline rings. The absorption and the fluorescence emission wavelength and quantum yields have been measured and correlated with the specific donor structures. Generally, inclusion of the donor in a ring annulated to the benzene or naphthalene aromatic (Ar) p-core results in a bathochromic shift of absorption and emission accompanied by an increase in the quantum yield. The left group in the diagram shows that the emission wavelength of a set of three fluorophores with n=0 and Ar = benzene with none, one or two tetrahydroquinoline rings and the same trend is observed in the right group with the same components except here n=1). Thus, the tetrahydroquinoline donor provides an efficient way to tailor the properties of fluorophores with substituted amines as electron-donating groups.

 

Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006