Donor-acceptor functionalized chromophores based on phenylacetylene/ethynylpyridine scaffoldings

ORGN 437

Eric L. Spitler, espitler@uoregon.edu and Michael M. Haley, haley@uoregon.edu. Department of Chemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403-1253
Highly conjugated carbon-rich compounds have been increasingly recognized as promising candidates for advanced optical and electronic device materials such as OLEDs and photovoltaic cells. Small conjugated organic molecules with spatially separated frontier molecular orbitals arising from electron donor-acceptor-functionalization (e.g., 1) can often lead to photonic properties ideal for such applications. Incorporation of pyridine rings as an acceptor unit allows systematic structure-property investigations that probe the optoelectronic consequences of small structural variations, including the location of the pyridyl nitrogen with respect to the conjugated bridge. Several such compounds have been synthesized, and the highly fluorescent intramolecular charge transfer compounds exhibit tunable emission spectra, strong solvatochromism, and dynamic response to ion complexation that provides potential as fluorescent sensors.