{"id":{"repo_id":"unr","oai_identifier":"oai:scholarwolf.unr.edu:11714/7468"},"canonical_url":"https://search.dev.ndltd.org/etd/unr/oai:scholarwolf.unr.edu:11714/7468","repository":{"repo_id":"unr","name":"University of Nevada - Reno","base_url":"https://scholarwolf.unr.edu/server/oai/request"},"display":{"title":"Synthesis of contorted nanographenes via multi-fold alkyne benzannulation reactions","abstract":"Nanographenes (NGs) of unique shape, size and properties are always at the center of attraction because of their potential application as semiconducting materials in organo-electronic devices. Contorted NGs have gained increased attention because of their fascinating molecular packing, reduced π-π interaction, enhanced solubility and lower band gap compared to the planar analogues. We have synthesized a library of contorted NGs by utilizing the non-oxidative, alkyne benzannu-lation reaction catalyzed by indium chloride and silver bis triflimide by exploiting high energy content of carbon-carbon triple bonds of the diyne precursors under a mild-reaction conditions. We employed two-fold InCl3/AgNTf2-catalyzed alkyne benzannulation reaction to afford a broad collection of highly functionalized, laterally π-expanded, [5]helicene-like naphtho[1,2-a]pyrene derivatives in moderate to very good yields. We were able to utilize this method to expand conju-gation of the HBC core to get a variety of π-extended HBC NGs. The Suzuki cross-coupling of the halogen(s) substituted smaller polycyclic aromatic hydrocarbons with diyne boronic ester gave polyalkyne precursors, which were subjected to multi-fold alkyne benzannulation reaction to af-ford larger, highly soluble contorted NGs. This work also proved the applicability InCl3 and AgNTf2 in the synthesis of up to six benzene ring in one-pot reaction condition. In most of the cases, the chiral, helically twisted skeletons were unambiguously determined through X-ray crys-tallography. We are also very close (two-steps away) towards the synthesis of longer pyrenacenes such as quateropyrene and quinteropyrene following our previous protocol for the synthesis of pyrene, peropyrene and teropyrene.","abstract_html":"Nanographenes (NGs) of unique shape, size and properties are always at the center of attraction because of their potential application as semiconducting materials in organo-electronic devices. Contorted NGs have gained increased attention because of their fascinating molecular packing, reduced π-π interaction, enhanced solubility and lower band gap compared to the planar analogues. We have synthesized a library of contorted NGs by utilizing the non-oxidative, alkyne benzannu-lation reaction catalyzed by indium chloride and silver bis triflimide by exploiting high energy content of carbon-carbon triple bonds of the diyne precursors under a mild-reaction conditions. We employed two-fold InCl3/AgNTf2-catalyzed alkyne benzannulation reaction to afford a broad collection of highly functionalized, laterally π-expanded, [5]helicene-like naphtho[1,2-a]pyrene derivatives in moderate to very good yields. We were able to utilize this method to expand conju-gation of the HBC core to get a variety of π-extended HBC NGs. The Suzuki cross-coupling of the halogen(s) substituted smaller polycyclic aromatic hydrocarbons with diyne boronic ester gave polyalkyne precursors, which were subjected to multi-fold alkyne benzannulation reaction to af-ford larger, highly soluble contorted NGs. This work also proved the applicability InCl3 and AgNTf2 in the synthesis of up to six benzene ring in one-pot reaction condition. In most of the cases, the chiral, helically twisted skeletons were unambiguously determined through X-ray crys-tallography. We are also very close (two-steps away) towards the synthesis of longer pyrenacenes such as quateropyrene and quinteropyrene following our previous protocol for the synthesis of pyrene, peropyrene and teropyrene.","abstract_has_math":false,"creators":["Sitaula, Paban"],"institution":null,"degree_name":null,"degree_level":"Doctorate Degree","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Chalifoux, Wesley A."],"committee_chairs":[],"committee_members":["Sheridan, Robert S.","Casey, Sean M.","Pinsky, Mark","Sengupta, Shamik"],"year":2020,"date_issued":"2020","date_published":"2020","updated_at":"2026-07-27T21:47:14Z","subjects":["Alkyne benzannulation reaction","Carbon rich material","Helical NGs","HBC NGs","Lewis acid","Nanographenes (NGs)","Twisted Nanographenes"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"http://hdl.handle.net/11714/7468","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Chalifoux, Wesley A."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Sheridan, Robert S.","Casey, Sean M.","Pinsky, Mark","Sengupta, Shamik"]},{"key":"dc:creator","label":"Author","values":["Sitaula, Paban"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2020-06-15T19:14:46Z"]},{"key":"dc:date.issued","label":"Date","values":["2020"]},{"key":"dc:type","label":"Dc Type","values":["Dissertation"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Doctorate Degree"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Alkyne benzannulation reaction","Carbon rich material","Helical NGs","HBC NGs","Lewis acid","Nanographenes (NGs)","Twisted Nanographenes"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/11714/7468"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Nanographenes (NGs) of unique shape, size and properties are always at the center of attraction because of their potential application as semiconducting materials in organo-electronic devices. Contorted NGs have gained increased attention because of their fascinating molecular packing, reduced π-π interaction, enhanced solubility and lower band gap compared to the planar analogues. We have synthesized a library of contorted NGs by utilizing the non-oxidative, alkyne benzannu-lation reaction catalyzed by indium chloride and silver bis triflimide by exploiting high energy content of carbon-carbon triple bonds of the diyne precursors under a mild-reaction conditions. We employed two-fold InCl3/AgNTf2-catalyzed alkyne benzannulation reaction to afford a broad collection of highly functionalized, laterally π-expanded, [5]helicene-like naphtho[1,2-a]pyrene derivatives in moderate to very good yields. We were able to utilize this method to expand conju-gation of the HBC core to get a variety of π-extended HBC NGs. The Suzuki cross-coupling of the halogen(s) substituted smaller polycyclic aromatic hydrocarbons with diyne boronic ester gave polyalkyne precursors, which were subjected to multi-fold alkyne benzannulation reaction to af-ford larger, highly soluble contorted NGs. This work also proved the applicability InCl3 and AgNTf2 in the synthesis of up to six benzene ring in one-pot reaction condition. In most of the cases, the chiral, helically twisted skeletons were unambiguously determined through X-ray crys-tallography. We are also very close (two-steps away) towards the synthesis of longer pyrenacenes such as quateropyrene and quinteropyrene following our previous protocol for the synthesis of pyrene, peropyrene and teropyrene."]},{"key":"dc:format","label":"Dc Format","values":["PDF"]},{"key":"dc:title","label":"Title","values":["Synthesis of contorted nanographenes via multi-fold alkyne benzannulation reactions"]}]}],"canonical_facts":{"dc:contributor.advisor":["Chalifoux, Wesley A."],"dc:contributor.committeemember":["Sheridan, Robert S.","Casey, Sean M.","Pinsky, Mark","Sengupta, Shamik"],"dc:creator":["Sitaula, Paban"],"dc:date.accessioned":["2020-06-15T19:14:46Z"],"dc:date.issued":["2020"],"dc:description.abstract":["Nanographenes (NGs) of unique shape, size and properties are always at the center of attraction because of their potential application as semiconducting materials in organo-electronic devices. Contorted NGs have gained increased attention because of their fascinating molecular packing, reduced π-π interaction, enhanced solubility and lower band gap compared to the planar analogues. We have synthesized a library of contorted NGs by utilizing the non-oxidative, alkyne benzannu-lation reaction catalyzed by indium chloride and silver bis triflimide by exploiting high energy content of carbon-carbon triple bonds of the diyne precursors under a mild-reaction conditions. We employed two-fold InCl3/AgNTf2-catalyzed alkyne benzannulation reaction to afford a broad collection of highly functionalized, laterally π-expanded, [5]helicene-like naphtho[1,2-a]pyrene derivatives in moderate to very good yields. We were able to utilize this method to expand conju-gation of the HBC core to get a variety of π-extended HBC NGs. The Suzuki cross-coupling of the halogen(s) substituted smaller polycyclic aromatic hydrocarbons with diyne boronic ester gave polyalkyne precursors, which were subjected to multi-fold alkyne benzannulation reaction to af-ford larger, highly soluble contorted NGs. This work also proved the applicability InCl3 and AgNTf2 in the synthesis of up to six benzene ring in one-pot reaction condition. In most of the cases, the chiral, helically twisted skeletons were unambiguously determined through X-ray crys-tallography. We are also very close (two-steps away) towards the synthesis of longer pyrenacenes such as quateropyrene and quinteropyrene following our previous protocol for the synthesis of pyrene, peropyrene and teropyrene."],"dc:format":["PDF"],"dc:identifier.uri":["http://hdl.handle.net/11714/7468"],"dc:subject":["Alkyne benzannulation reaction","Carbon rich material","Helical NGs","HBC NGs","Lewis acid","Nanographenes (NGs)","Twisted Nanographenes"],"dc:title":["Synthesis of contorted nanographenes via multi-fold alkyne benzannulation reactions"],"dc:type":["Dissertation"],"thesis:degree_level":["Doctorate Degree"]},"updated_at":"2026-07-27T21:47:14Z"}