Macrocyclic thiourea and thioamide receptor synthesis and utilization

Tutkielman teoreettinen osa käsittelee makrosyklisten tioamidi- ja tioureareseptorien synteesimenetelmiä ja sovelluksia supramolekyylikemian tutkimuksessa. Käsitellyt reseptorit ovat jaoteltu sitoutumisominaisuuksiensa perusteella. Pääpaino on reseptorien synteettisten proseduurien ja kompleksaatiot...

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Main Author: Peshev, Ivan
Other Authors: Matemaattis-luonnontieteellinen tiedekunta, Faculty of Sciences, Kemian laitos, Department of Chemistry, Jyväskylän yliopisto, University of Jyväskylä
Format: Master's thesis
Language:eng
Published: 2020
Subjects:
Online Access: https://jyx.jyu.fi/handle/123456789/68863
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author Peshev, Ivan
author2 Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_facet Peshev, Ivan Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä Peshev, Ivan Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_sort Peshev, Ivan
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description Tutkielman teoreettinen osa käsittelee makrosyklisten tioamidi- ja tioureareseptorien synteesimenetelmiä ja sovelluksia supramolekyylikemian tutkimuksessa. Käsitellyt reseptorit ovat jaoteltu sitoutumisominaisuuksiensa perusteella. Pääpaino on reseptorien synteettisten proseduurien ja kompleksaatiotutkimusten käsittelyssä. Kirjallinen osa sisältää myös johdantokappaleen, jossa käsitellään tutkielman kannalta relevantteja ilmiöitä supramolekyylikemian tutkimuksessa. Kokeellisen osan tavoitteena oli syntetisoida useita tioureayksiköitä sisältäviä asyklisiä ja makrosyklisiä reseptoreita. Lisäksi testattiin osan onnistuneesti syntetisoitujen tuotteiden halogeenisitoutumiskyky jodia sisältäviä yhdisteitä kohtaan. Kompleksaatiotutkimukset suoritettiin reseptorien kiteytysyritysten kautta analysoimalla muodostuneita rakenteita röntgenkristallografialla. Halogeenisitoutumista seurattiin myös 1H ja 13C NMR tekniikoiden avulla. Työssä saatiin muodostettua halogeenisidos tripodaalisten tioureareseptorien ja perfluorattujen jodibentseeniyhdisteiden välille. Kompleksaatiotutkimusten tulokset osoittivat, että puhtaan jodin lisäys johtaa reseptorien hajoamiseen ja elementaarisen rikin vapautumiseen. The theoretical part of the thesis discusses the synthetic procedures for thioamide and thiourea macrocyclic receptors and their utilization in supramolecular chemistry research. Covered receptors are organized based on their binding properties towards guests. The focus is on synthetic procedures and conducted complexation studies of macrocyclic thiocarbonyl structures. Theoretical work contains also an introductory part discussing the main principles of supramolecular chemistry that are related to the topic. The experimental part aimed to synthesize various acyclic and macrocyclic receptors containing several thiourea moieties. Part of the successfully synthesized structures were tested for halogen bonding abilities towards guests containing iodine. Complexation studies were mostly carried in the solid-state by preparation of crystallization samples. Some endeavors also included 1H and 13C NMR binding studies. Successful attempts for halogen bond formation were achieved between tripodal thiourea receptors and perfluorinated iodobenzene guests. Results showed that the addition of pure iodine caused receptor decomposition and formation of elemental sulfur.
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spellingShingle Peshev, Ivan Macrocyclic thiourea and thioamide receptor synthesis and utilization Orgaaninen kemia Organic Chemistry 4035 supramolekulaarinen kemia orgaaninen kemia vetysidokset halogeenit reseptorit kiteet jodi supramolecular chemistry organic chemistry hydrogen bonds halogens receptors crystals iodine
title Macrocyclic thiourea and thioamide receptor synthesis and utilization
title_full Macrocyclic thiourea and thioamide receptor synthesis and utilization
title_fullStr Macrocyclic thiourea and thioamide receptor synthesis and utilization Macrocyclic thiourea and thioamide receptor synthesis and utilization
title_full_unstemmed Macrocyclic thiourea and thioamide receptor synthesis and utilization Macrocyclic thiourea and thioamide receptor synthesis and utilization
title_short Macrocyclic thiourea and thioamide receptor synthesis and utilization
title_sort macrocyclic thiourea and thioamide receptor synthesis and utilization
title_txtP Macrocyclic thiourea and thioamide receptor synthesis and utilization
topic Orgaaninen kemia Organic Chemistry 4035 supramolekulaarinen kemia orgaaninen kemia vetysidokset halogeenit reseptorit kiteet jodi supramolecular chemistry organic chemistry hydrogen bonds halogens receptors crystals iodine
topic_facet 4035 Orgaaninen kemia Organic Chemistry crystals halogeenit halogens hydrogen bonds iodine jodi kiteet orgaaninen kemia organic chemistry receptors reseptorit supramolecular chemistry supramolekulaarinen kemia vetysidokset
url https://jyx.jyu.fi/handle/123456789/68863 http://www.urn.fi/URN:NBN:fi:jyu-202005063074
work_keys_str_mv AT peshevivan macrocyclicthioureaandthioamidereceptorsynthesisandutilization