ORGN 118 |
| We have previously shown that aliphatic hydrocarbons and fluorocarbons help to direct the packing of electron-rich and -poor aromatic moieties. In the present work, we report the synthesis and characterization of a series of donor-acceptor dyads based on oligothiophenes (donor) and naphthalene diimides (acceptor). The donors bear aliphatic hydrocarbon side-chains while the acceptors bear aliphatic fluorocarbon side-chains. The halves of the dyads are connected by flexible tethers, assembled via “click” chemistry. Results of spectroscopic measurements (UV-vis, time-resolved fluorescence) reveal interactions between the parts of the dyads. Cyclic voltammetry of the quarterthiophene molecules led to their electrochemical polymerization, as evidenced by deposition of purple precipitates onto the working electrode. The phase behavior of the dyads, determined by DSC and optical microscopy, is also presented in light of the effects of the fluorocarbon side-chains.
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
