{"id":{"repo_id":"vilnius","oai_identifier":"oai:vu.lt:elaba:11736637"},"canonical_url":"https://search.dev.ndltd.org/etd/vilnius/oai:vu.lt:elaba:11736637","repository":{"repo_id":"vilnius","name":"Vilnius University","base_url":"https://epublications.vu.lt/oai"},"display":{"title":"Pirolo[2,3-d]pirimidino π-konjuguotų fluoroforų, turinčių 1,2,3-triazolo ir etinil jungtukus, sintezė ir fotofizikinės savybės /","abstract":"The main goal of the work was to synthesize pyrrolo[2,3-d]pyrimidine-core based oligoarylenes with ethynyl and 1,2,3-triazole linkers and to evaluate their photophysical properties. Novel chromophores - 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared by CuAAC reaction. It was demonstrated that in the CuAAC reaction of 2,4-diazidopyrrolo[2,3-d]pyrimidine along with 1,4-disubstituted 1,2,3-triazoles some amounts of 1,5-disubstituted isomers were formed. The synthesized 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolopyrimidines exhibit efficient fluorescence in the range from 402 nm to 650 nm. A comparative study of Sonogashira and Stille reactions as well as Suzuki and Stille reactions for the introduction of alkynyl and aryl moieties onto pyrrolo[2,3-d]pyrimidine has been carried out. The synthesis of pyrrolo[2,3-d]pyrimidine oligoarylenes bearing different alkynyl and aryl substituents can be accomplished by applying two-step processes: Sonogashira – Stille or Stille – Stille. Likewise, 2,4-bis(arylethynyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidines bearing the same substituents can be obtained by one step Stille coupling starting from 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. Pd(PPh3)2Cl2/AsPPh3 has emerged as suitable catalyst system for Stille alkynylation and arylation reactions providing the desired products in good yields. The developed protocol allows a wide library of novel 2-aryl-4-(arylethynyl)pyrrolo[2,3-d]pyrimidines and 2,4-bis(arylethynyl)pyrrolo[2,3-d]pyrimidines to be generated, including those with different arylethynyl groups in positions 2 and 4 of the heterocycle.","abstract_html":"The main goal of the work was to synthesize pyrrolo[2,3-d]pyrimidine-core based oligoarylenes with ethynyl and 1,2,3-triazole linkers and to evaluate their photophysical properties. Novel chromophores - 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared by CuAAC reaction. It was demonstrated that in the CuAAC reaction of 2,4-diazidopyrrolo[2,3-d]pyrimidine along with 1,4-disubstituted 1,2,3-triazoles some amounts of 1,5-disubstituted isomers were formed. The synthesized 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolopyrimidines exhibit efficient fluorescence in the range from 402 nm to 650 nm. A comparative study of Sonogashira and Stille reactions as well as Suzuki and Stille reactions for the introduction of alkynyl and aryl moieties onto pyrrolo[2,3-d]pyrimidine has been carried out. The synthesis of pyrrolo[2,3-d]pyrimidine oligoarylenes bearing different alkynyl and aryl substituents can be accomplished by applying two-step processes: Sonogashira – Stille or Stille – Stille. Likewise, 2,4-bis(arylethynyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidines bearing the same substituents can be obtained by one step Stille coupling starting from 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. Pd(PPh3)2Cl2/AsPPh3 has emerged as suitable catalyst system for Stille alkynylation and arylation reactions providing the desired products in good yields. The developed protocol allows a wide library of novel 2-aryl-4-(arylethynyl)pyrrolo[2,3-d]pyrimidines and 2,4-bis(arylethynyl)pyrrolo[2,3-d]pyrimidines to be generated, including those with different arylethynyl groups in positions 2 and 4 of the heterocycle.","abstract_has_math":false,"creators":["Bucevičius, Jonas,"],"institution":"Institutional Repository of Vilnius University","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015","date_published":"2015","updated_at":"2026-07-24T05:55:31Z","subjects":["Pyrrolo[2,3-d]pyrimidine ; fluorescence ; palladium catalyzed reactions ; 1,2,3-triazoles ; cycloaddition"],"languages":["lit"],"rights":["info:eu-repo/semantics/openAccess"],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://repository.vu.lt/VU:ELABAETD11736637&prefLang=en_US","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Bucevičius, Jonas,"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015"]},{"key":"dc:publisher","label":"Institution","values":["Institutional Repository of Vilnius University"]},{"key":"dc:relation","label":"Dc Relation","values":["https://epublications.vu.lt/object/elaba:11736637/11736637.pdf"]},{"key":"dc:type","label":"Dc Type","values":["info:eu-repo/semantics/doctoralThesis"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Pyrrolo[2,3-d]pyrimidine ; fluorescence ; palladium catalyzed reactions ; 1,2,3-triazoles ; cycloaddition"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["lit"]},{"key":"dc:rights","label":"Dc Rights","values":["info:eu-repo/semantics/openAccess"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://repository.vu.lt/VU:ELABAETD11736637&prefLang=en_US"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The main goal of the work was to synthesize pyrrolo[2,3-d]pyrimidine-core based oligoarylenes with ethynyl and 1,2,3-triazole linkers and to evaluate their photophysical properties. Novel chromophores - 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared by CuAAC reaction. It was demonstrated that in the CuAAC reaction of 2,4-diazidopyrrolo[2,3-d]pyrimidine along with 1,4-disubstituted 1,2,3-triazoles some amounts of 1,5-disubstituted isomers were formed. The synthesized 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolopyrimidines exhibit efficient fluorescence in the range from 402 nm to 650 nm. A comparative study of Sonogashira and Stille reactions as well as Suzuki and Stille reactions for the introduction of alkynyl and aryl moieties onto pyrrolo[2,3-d]pyrimidine has been carried out. The synthesis of pyrrolo[2,3-d]pyrimidine oligoarylenes bearing different alkynyl and aryl substituents can be accomplished by applying two-step processes: Sonogashira – Stille or Stille – Stille. Likewise, 2,4-bis(arylethynyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidines bearing the same substituents can be obtained by one step Stille coupling starting from 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. Pd(PPh3)2Cl2/AsPPh3 has emerged as suitable catalyst system for Stille alkynylation and arylation reactions providing the desired products in good yields. The developed protocol allows a wide library of novel 2-aryl-4-(arylethynyl)pyrrolo[2,3-d]pyrimidines and 2,4-bis(arylethynyl)pyrrolo[2,3-d]pyrimidines to be generated, including those with different arylethynyl groups in positions 2 and 4 of the heterocycle."]},{"key":"dc:format","label":"Dc Format","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Pirolo[2,3-d]pirimidino π-konjuguotų fluoroforų, turinčių 1,2,3-triazolo ir etinil jungtukus, sintezė ir fotofizikinės savybės /","Pyrrolo[2,3-d]pyrimidine-based π-conjugated fluorophores with 1,2,3-triazole and ethynyl linkers: synthesis and photophysical properties."]}]}],"canonical_facts":{"dc:creator":["Bucevičius, Jonas,"],"dc:date":["2015"],"dc:description":["The main goal of the work was to synthesize pyrrolo[2,3-d]pyrimidine-core based oligoarylenes with ethynyl and 1,2,3-triazole linkers and to evaluate their photophysical properties. Novel chromophores - 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolo[2,3-d]pyrimidines were prepared by CuAAC reaction. It was demonstrated that in the CuAAC reaction of 2,4-diazidopyrrolo[2,3-d]pyrimidine along with 1,4-disubstituted 1,2,3-triazoles some amounts of 1,5-disubstituted isomers were formed. The synthesized 2,4-bis(4-aryl-1,2,3-triazol-1-yl)pyrrolopyrimidines exhibit efficient fluorescence in the range from 402 nm to 650 nm. A comparative study of Sonogashira and Stille reactions as well as Suzuki and Stille reactions for the introduction of alkynyl and aryl moieties onto pyrrolo[2,3-d]pyrimidine has been carried out. The synthesis of pyrrolo[2,3-d]pyrimidine oligoarylenes bearing different alkynyl and aryl substituents can be accomplished by applying two-step processes: Sonogashira – Stille or Stille – Stille. Likewise, 2,4-bis(arylethynyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidines bearing the same substituents can be obtained by one step Stille coupling starting from 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine. Pd(PPh3)2Cl2/AsPPh3 has emerged as suitable catalyst system for Stille alkynylation and arylation reactions providing the desired products in good yields. The developed protocol allows a wide library of novel 2-aryl-4-(arylethynyl)pyrrolo[2,3-d]pyrimidines and 2,4-bis(arylethynyl)pyrrolo[2,3-d]pyrimidines to be generated, including those with different arylethynyl groups in positions 2 and 4 of the heterocycle."],"dc:format":["application/pdf"],"dc:identifier":["https://repository.vu.lt/VU:ELABAETD11736637&prefLang=en_US"],"dc:language":["lit"],"dc:publisher":["Institutional Repository of Vilnius University"],"dc:relation":["https://epublications.vu.lt/object/elaba:11736637/11736637.pdf"],"dc:rights":["info:eu-repo/semantics/openAccess"],"dc:subject":["Pyrrolo[2,3-d]pyrimidine ; fluorescence ; palladium catalyzed reactions ; 1,2,3-triazoles ; cycloaddition"],"dc:title":["Pirolo[2,3-d]pirimidino π-konjuguotų fluoroforų, turinčių 1,2,3-triazolo ir etinil jungtukus, sintezė ir fotofizikinės savybės /","Pyrrolo[2,3-d]pyrimidine-based π-conjugated fluorophores with 1,2,3-triazole and ethynyl linkers: synthesis and photophysical properties."],"dc:type":["info:eu-repo/semantics/doctoralThesis"]},"updated_at":"2026-07-24T05:55:31Z"}