{"id":{"repo_id":"uwo","oai_identifier":"oai:uwo.scholaris.ca:20.500.14721/19925"},"canonical_url":"https://search.dev.ndltd.org/etd/uwo/oai:uwo.scholaris.ca:20.500.14721/19925","repository":{"repo_id":"uwo","name":"Western University","base_url":"https://uwo.scholaris.ca/server/oai/request"},"display":{"title":"C2- and C3-Symmetric Meta-substituted Thienyl Benzenes: A Comparative Synthetic and Structural Study","abstract":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Cornacchio, Angelica Lee Petrina"],"institution":null,"degree_name":"M Sc","degree_level":null,"degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["Jones, Nathan"],"committee_chairs":[],"committee_members":[],"year":2007,"date_issued":"2007-01-01","date_published":"2007-01-01","updated_at":"2026-07-27T21:56:16Z","subjects":[],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/20.500.14721/19925","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Jones, Nathan"]},{"key":"dc:creator","label":"Author","values":["Cornacchio, Angelica Lee Petrina"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2025-06-25T19:12:20Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2025-06-25T19:12:20Z"]},{"key":"dc:date.issued","label":"Date","values":["2007-01-01"]},{"key":"dc:type","label":"Dc Type","values":["thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_name","label":"Degree Name","values":["M Sc"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/20.500.14721/19925"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:title","label":"Title","values":["C2- and C3-Symmetric Meta-substituted Thienyl Benzenes: A Comparative Synthetic and Structural Study"]}]}],"canonical_facts":{"dc:contributor.advisor":["Jones, Nathan"],"dc:creator":["Cornacchio, Angelica Lee Petrina"],"dc:date.accessioned":["2025-06-25T19:12:20Z"],"dc:date.available":["2025-06-25T19:12:20Z"],"dc:date.issued":["2007-01-01"],"dc:description.abstract":["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."],"dc:identifier.uri":["https://hdl.handle.net/20.500.14721/19925"],"dc:title":["C2- and C3-Symmetric Meta-substituted Thienyl Benzenes: A Comparative Synthetic and Structural Study"],"dc:type":["thesis"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_name":["M Sc"]},"updated_at":"2026-07-27T21:56:16Z"}