Grant: Discovery Grants Program - Individual

The general aim of this proposed research is to broaden the basic knowledge we have been developing over the past years in the field of organic synthesis and to exploit this expertise to synthesize and characterize new organic molecules with properties that render them candidates for incorporation in organic electronic devices (e.g. organic light-emitting diodes, field effect transistors) and/or testing for biological activity (e.g. anti-cancer, anti-inflammatory). The focal points of this proposal are a specific class of molecules called pyrenophanes and a particular chemical reaction called the inverse electron demand Diels-Alder (IEDDA) reaction. We have developed a very effective method for synthesizing pyrenophanes, which are potentially useful in organic electronic devices because of the rich photochemistry and photophysics associated with the main part of the molecule (a pyrene system). We propose to synthesize a broad range of new pyrenophanes with new and unusual structures and fully characterize the products wth an eye to potential application in devices. The IEDDA reaction is an infrequently used variant of one of the most useful reactions in the field of organic chemistry. We have developed a class of IEDDA reactions that lead to the formation of certain heterocyclic aromatic compounds (xanthones and benzocoumarins) that are not only subunits of many naturally occurring and biologically active (e.g. anti-cancer, anti-inflammatory) compounds, but also can possess interesting and potentially useful optical properties. We propose to use our IEDDA chemistry to synthesize and characterize a variety of xanthone and bezocoumarin-based molecules with an eye to potential application in devices as therapeutic agents. The proposed research is fundamental in nature and deals primarily with synthesis and characterization. The design and fabrication of organic electronic devices is beyond the scope of this proposal.