C2- and C3-Symmetric Meta-substituted Thienyl Benzenes: A Comparative Synthetic and Structural Study

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.

Name thesis:degree_name

M Sc

Discipline thesis:degree_discipline

Chemistry

Year dc:date.issued

2007

Author dc:creator

• Cornacchio, Angelica Lee Petrina

Advisor dc:contributor.advisor

• Jones, Nathan

Handle dc:identifier.uri

https://hdl.handle.net/20.500.14721/19925

OAI identifier oai:identifier

oai:uwo.scholaris.ca:20.500.14721/19925