Date of Award


Degree Type


Degree Name

Master of Science




Dr. Nathan Jones


Suzuki, Stille and Kumada coupling approaches to the syntheses of various C1- and C3- symmetric thienylbenzene compounds (A and B, respectively) are systematically compared. Novel routes are reported for the syntheses of C3-symmetric compounds using Kumada (n = 0) and Stille (n = 1) coupling reactions. Potentiodynamic treatment of these compounds produces polymers whose properties as a function of the length of the thienyl substituent (n= 1 vs. n = 2), and of cross-linking (C2 vs. C3), are compared. The solidstate structures of C2- and C3-symmetric (n = 1) compounds are also discussed. Furthermore, the syntheses of novel meta-substituted benzenes that bear both thiophene and halogen groups are reported (C, n = 0 or 1). Further elaboration of the third meta position using Kumada, Stille and Sonogashira coupling methods gives a family of C2-symmetric compounds of the general structure l,3-bis(thienyl)-5-R-benzene, where R is either an electron-donating or -withdrawing group. The physical and optical properties of these compounds are compared using spectroscopic (UV-visible absorption and fluorescence) and electrochemical measurements. The anodic peak potentials (Epa) obtained for these compounds do not correlate with their σm Hammett parameters.



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