Calix[4]pyrroles in environmental and green chemistry applications

Kaliks[4]pyrrolit ovat kemiallisesti merkittävä makrosyklien ryhmä, joka tunnetaan kyvystään toimia monipuolisina supramolekulaarisina isäntärakenteina. Ne voivat muodostaa isäntä-vieras-komplekseja sekä ionisten yhdisteiden että neutraalien molekyylien kanssa. Niiden konformaatiojoustavuus on keske...

Täydet tiedot

Bibliografiset tiedot
Päätekijä: Kangas, Aliisa
Muut tekijät: Matemaattis-luonnontieteellinen tiedekunta, Faculty of Sciences, Kemian laitos, Department of Chemistry, Jyväskylän yliopisto, University of Jyväskylä
Aineistotyyppi: Pro gradu
Kieli:eng
Julkaistu: 2025
Aiheet:
Linkit: https://jyx.jyu.fi/handle/123456789/103064
_version_ 1834222500979933184
author Kangas, Aliisa
author2 Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_facet Kangas, Aliisa Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä Kangas, Aliisa Matemaattis-luonnontieteellinen tiedekunta Faculty of Sciences Kemian laitos Department of Chemistry Jyväskylän yliopisto University of Jyväskylä
author_sort Kangas, Aliisa
datasource_str_mv jyx
description Kaliks[4]pyrrolit ovat kemiallisesti merkittävä makrosyklien ryhmä, joka tunnetaan kyvystään toimia monipuolisina supramolekulaarisina isäntärakenteina. Ne voivat muodostaa isäntä-vieras-komplekseja sekä ionisten yhdisteiden että neutraalien molekyylien kanssa. Niiden konformaatiojoustavuus on keskeisessä roolissa molekyylien tunnistuksessa, erityisesti anionien aiheuttamien rakennemuutosten kautta, jotka mahdollistavat ioniparien yhteistoiminnallisen sitoutumisen. Helpon synteesin, rakenteellisen muunneltavuuden ja vahvan sitoutumiskyvyn ansiosta kaliks[4]pyrrolit ovat nousseet lupaaviksi yhdisteiksi molekyylitunnistuksessa ja ympäristön puhdistusteknologioissa. Niiden soveltamista vesipitoisiin ympäristöihin rajoittaa kuitenkin heikko vesiliukoisuus, minkä vuoksi funktionalisointia hydrofiilisillä ryhmillä on tutkittu yhteensopivuuden parantamiseksi vesipohjaisten järjestelmien kanssa. Tämä pro gradu -tutkielma sisältää kirjallisuuskatsauksen isäntä-vieras-kemiaan, keskittyen erityisesti kaliks[4]pyrroleihin. Katsauksessa käsitellään näiden yhdisteiden molekyylirakennetta, fysikaaliskemiallisia ominaisuuksia sekä synteesistrategioita, mukaan lukien perinteiset ja vihreän kemian mukaiset menetelmät, joilla pyritään vähentämään ympäristökuormitusta. Lisäksi tarkastellaan kaliks[4]pyrrolien soveltuvuutta ympäristökemiaan, erityisesti ionisten ja neutraalien haitta-aineiden poistamiseen vesiliuoksista neste-neste- ja polymeerisorbenttipohjaisten uuttomenetelmien avulla. Kokeellinen osio kuvaa kaliks[4]pyrrolien synteesiä ja PEGylaatiota, jonka tavoitteena oli parantaa yhdisteiden vesiliukoisuutta. Yhtä onnistuneesti PEGyloitua kaliks[4]pyrrolia hyödynnettiin misellimuodostuksessa yhdessä ei-ionisen pinta-aktiivisen aineen kanssa. Muodostuneita supramolekulaarisia järjestelmiä karakterisoitiin erilaisin analyyttisin menetelmin niiden rakenteen ja mahdollisen käytön arvioimiseksi uuttosovelluksissa. Calix[4]pyrroles are a chemically significant class of macrocycles, known for their ability to act as versatile supramolecular hosts capable of forming host-guest complexes with both ionic compounds and neutral molecules. Their conformational flexibility plays a central role in their molecular recognition behavior, particularly through anion-induced structural changes that enable cooperative binding of ion pairs. Due to their ease of synthesis, structural tunability, and strong binding affinities, calix[4]pyrroles have emerged as promising candidates for applications in molecular recognition and environmental remediation technologies. However, one of the main challenges hindering their broader application in aqueous environments is their generally poor water solubility. To address this, increasing attention has been directed toward functionalizing calix[4]pyrroles with hydrophilic groups to improve their compatibility with water-based systems. This master’s thesis presents a literature review on host-guest chemistry, with a specific focus on calix[4]pyrroles. It covers their molecular structure, physicochemical properties, and both conventional synthetic strategies and green chemistry approaches aimed at minimizing environmental impact. In addition, their role in environmental chemistry is explored, particularly regarding the removal of harmful ionic and neutral pollutants from aqueous solutions through liquid-liquid and polymer sorbent-based extraction methods. The experimental part describes the synthesis of calix[4]pyrroles and their subsequent PEGylation. One successfully synthesized PEGylated calix[4]pyrrole was used in co-micellization with a non-ionic surfactant to form micellar assemblies. These supramolecular systems were characterized using various analytical techniques to evaluate their structure and potential as extraction media.
first_indexed 2025-06-04T20:05:47Z
format Pro gradu
free_online_boolean 1
fullrecord [{"key": "dc.contributor.advisor", "value": "Helttunen, Kaisa", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.advisor", "value": "Naulap\u00e4\u00e4, Julia", "language": null, "element": "contributor", "qualifier": "advisor", "schema": "dc"}, {"key": "dc.contributor.author", "value": "Kangas, Aliisa", "language": null, "element": "contributor", "qualifier": "author", "schema": "dc"}, {"key": "dc.date.accessioned", "value": "2025-06-04T08:44:29Z", "language": null, "element": "date", "qualifier": "accessioned", "schema": "dc"}, {"key": "dc.date.available", "value": "2025-06-04T08:44:29Z", "language": null, "element": "date", "qualifier": "available", "schema": "dc"}, {"key": "dc.date.issued", "value": "2025", "language": null, "element": "date", "qualifier": "issued", "schema": "dc"}, {"key": "dc.identifier.uri", "value": "https://jyx.jyu.fi/handle/123456789/103064", "language": null, "element": "identifier", "qualifier": "uri", "schema": "dc"}, {"key": "dc.description.abstract", "value": "Kaliks[4]pyrrolit ovat kemiallisesti merkitt\u00e4v\u00e4 makrosyklien ryhm\u00e4, joka tunnetaan kyvyst\u00e4\u00e4n toimia monipuolisina supramolekulaarisina is\u00e4nt\u00e4rakenteina. Ne voivat muodostaa is\u00e4nt\u00e4-vieras-komplekseja sek\u00e4 ionisten yhdisteiden ett\u00e4 neutraalien molekyylien kanssa. Niiden konformaatiojoustavuus on keskeisess\u00e4 roolissa molekyylien tunnistuksessa, erityisesti anionien aiheuttamien rakennemuutosten kautta, jotka mahdollistavat ioniparien yhteistoiminnallisen sitoutumisen. Helpon synteesin, rakenteellisen muunneltavuuden ja vahvan sitoutumiskyvyn ansiosta kaliks[4]pyrrolit ovat nousseet lupaaviksi yhdisteiksi molekyylitunnistuksessa ja ymp\u00e4rist\u00f6n puhdistusteknologioissa. Niiden soveltamista vesipitoisiin ymp\u00e4rist\u00f6ihin rajoittaa kuitenkin heikko vesiliukoisuus, mink\u00e4 vuoksi funktionalisointia hydrofiilisill\u00e4 ryhmill\u00e4 on tutkittu yhteensopivuuden parantamiseksi vesipohjaisten j\u00e4rjestelmien kanssa.\n\nT\u00e4m\u00e4 pro gradu -tutkielma sis\u00e4lt\u00e4\u00e4 kirjallisuuskatsauksen is\u00e4nt\u00e4-vieras-kemiaan, keskittyen erityisesti kaliks[4]pyrroleihin. Katsauksessa k\u00e4sitell\u00e4\u00e4n n\u00e4iden yhdisteiden molekyylirakennetta, fysikaaliskemiallisia ominaisuuksia sek\u00e4 synteesistrategioita, mukaan lukien perinteiset ja vihre\u00e4n kemian mukaiset menetelm\u00e4t, joilla pyrit\u00e4\u00e4n v\u00e4hent\u00e4m\u00e4\u00e4n ymp\u00e4rist\u00f6kuormitusta. Lis\u00e4ksi tarkastellaan kaliks[4]pyrrolien soveltuvuutta ymp\u00e4rist\u00f6kemiaan, erityisesti ionisten ja neutraalien haitta-aineiden poistamiseen vesiliuoksista neste-neste- ja polymeerisorbenttipohjaisten uuttomenetelmien avulla.\n\nKokeellinen osio kuvaa kaliks[4]pyrrolien synteesi\u00e4 ja PEGylaatiota, jonka tavoitteena oli parantaa yhdisteiden vesiliukoisuutta. Yht\u00e4 onnistuneesti PEGyloitua kaliks[4]pyrrolia hy\u00f6dynnettiin misellimuodostuksessa yhdess\u00e4 ei-ionisen pinta-aktiivisen aineen kanssa. Muodostuneita supramolekulaarisia j\u00e4rjestelmi\u00e4 karakterisoitiin erilaisin analyyttisin menetelmin niiden rakenteen ja mahdollisen k\u00e4yt\u00f6n arvioimiseksi uuttosovelluksissa.", "language": "fi", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.abstract", "value": "Calix[4]pyrroles are a chemically significant class of macrocycles, known for their ability to act as versatile supramolecular hosts capable of forming host-guest complexes with both ionic compounds and neutral molecules. Their conformational flexibility plays a central role in their molecular recognition behavior, particularly through anion-induced structural changes that enable cooperative binding of ion pairs. Due to their ease of synthesis, structural tunability, and strong binding affinities, calix[4]pyrroles have emerged as promising candidates for applications in molecular recognition and environmental remediation technologies. However, one of the main challenges hindering their broader application in aqueous environments is their generally poor water solubility. To address this, increasing attention has been directed toward functionalizing calix[4]pyrroles with hydrophilic groups to improve their compatibility with water-based systems.\n\nThis master\u2019s thesis presents a literature review on host-guest chemistry, with a specific focus on calix[4]pyrroles. It covers their molecular structure, physicochemical properties, and both conventional synthetic strategies and green chemistry approaches aimed at minimizing environmental impact. In addition, their role in environmental chemistry is explored, particularly regarding the removal of harmful ionic and neutral pollutants from aqueous solutions through liquid-liquid and polymer sorbent-based extraction methods.\n\nThe experimental part describes the synthesis of calix[4]pyrroles and their subsequent PEGylation. One successfully synthesized PEGylated calix[4]pyrrole was used in co-micellization with a non-ionic surfactant to form micellar assemblies. These supramolecular systems were characterized using various analytical techniques to evaluate their structure and potential as extraction media.", "language": "en", "element": "description", "qualifier": "abstract", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Submitted by Paivi Vuorio (paelvuor@jyu.fi) on 2025-06-04T08:44:29Z\nNo. of bitstreams: 0", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.description.provenance", "value": "Made available in DSpace on 2025-06-04T08:44:29Z (GMT). No. of bitstreams: 0\n Previous issue date: 2025", "language": "en", "element": "description", "qualifier": "provenance", "schema": "dc"}, {"key": "dc.format.extent", "value": "102", "language": null, "element": "format", "qualifier": "extent", "schema": "dc"}, {"key": "dc.language.iso", "value": "eng", "language": null, "element": "language", "qualifier": "iso", "schema": "dc"}, {"key": "dc.rights", "value": "In Copyright", "language": null, "element": "rights", "qualifier": null, "schema": "dc"}, {"key": "dc.subject.other", "value": "calix[4]pyrroles", "language": null, "element": "subject", "qualifier": "other", "schema": "dc"}, {"key": "dc.title", "value": "Calix[4]pyrroles in environmental and green chemistry applications", "language": null, "element": "title", "qualifier": null, "schema": "dc"}, {"key": "dc.type", "value": "master thesis", "language": null, "element": "type", "qualifier": null, "schema": "dc"}, {"key": "dc.identifier.urn", "value": "URN:NBN:fi:jyu-202506044868", "language": null, "element": "identifier", "qualifier": "urn", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Matemaattis-luonnontieteellinen tiedekunta", "language": "fi", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.faculty", "value": "Faculty of Sciences", "language": "en", "element": "contributor", "qualifier": "faculty", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Kemian laitos", "language": "fi", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.department", "value": "Department of Chemistry", "language": "en", "element": "contributor", "qualifier": "department", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "Jyv\u00e4skyl\u00e4n yliopisto", "language": null, "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.contributor.organization", "value": "University of Jyv\u00e4skyl\u00e4", "language": null, "element": "contributor", "qualifier": "organization", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Orgaaninen kemia", "language": "fi", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "dc.subject.discipline", "value": "Organic Chemistry", "language": "en", "element": "subject", "qualifier": "discipline", "schema": "dc"}, {"key": "dc.type.coar", "value": "http://purl.org/coar/resource_type/c_bdcc", "language": null, "element": "type", "qualifier": "coar", "schema": "dc"}, {"key": "dc.rights.copyright", "value": "\u00a9 The Author(s)", "language": "fi", "element": "rights", "qualifier": "copyright", "schema": "dc"}, {"key": "dc.rights.accesslevel", "value": "openAccess", "language": null, "element": "rights", "qualifier": "accesslevel", "schema": "dc"}, {"key": "dc.type.publication", "value": "masterThesis", "language": null, "element": "type", "qualifier": "publication", "schema": "dc"}, {"key": "dc.subject.yso", "value": "uutto", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "saasteet", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "ymp\u00e4rist\u00f6kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "orgaaninen kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "vihre\u00e4 kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "ionit", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "supramolekulaarinen kemia", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.subject.yso", "value": "synteesi", "language": null, "element": "subject", "qualifier": "yso", "schema": "dc"}, {"key": "dc.rights.url", "value": "https://rightsstatements.org/page/InC/1.0/", "language": null, "element": "rights", "qualifier": "url", "schema": "dc"}]
id jyx.123456789_103064
language eng
last_indexed 2025-06-04T20:05:47Z
main_date 2025-01-01T00:00:00Z
main_date_str 2025
online_boolean 1
online_urls_str_mv {"url":"https:\/\/jyx.jyu.fi\/bitstreams\/f6459266-7f6e-4db9-b99e-c9d500828c41\/download","text":"URN:NBN:fi:jyu-202506044868.pdf","source":"jyx","mediaType":"application\/pdf"}
publishDate 2025
record_format qdc
source_str_mv jyx
spellingShingle Kangas, Aliisa Calix[4]pyrroles in environmental and green chemistry applications calix[4]pyrroles Orgaaninen kemia Organic Chemistry uutto saasteet ympäristökemia orgaaninen kemia vihreä kemia ionit supramolekulaarinen kemia synteesi
title Calix[4]pyrroles in environmental and green chemistry applications
title_full Calix[4]pyrroles in environmental and green chemistry applications
title_fullStr Calix[4]pyrroles in environmental and green chemistry applications Calix[4]pyrroles in environmental and green chemistry applications
title_full_unstemmed Calix[4]pyrroles in environmental and green chemistry applications Calix[4]pyrroles in environmental and green chemistry applications
title_short Calix[4]pyrroles in environmental and green chemistry applications
title_sort calix 4 pyrroles in environmental and green chemistry applications
title_txtP Calix[4]pyrroles in environmental and green chemistry applications
topic calix[4]pyrroles Orgaaninen kemia Organic Chemistry uutto saasteet ympäristökemia orgaaninen kemia vihreä kemia ionit supramolekulaarinen kemia synteesi
topic_facet Orgaaninen kemia Organic Chemistry calix[4]pyrroles ionit orgaaninen kemia saasteet supramolekulaarinen kemia synteesi uutto vihreä kemia ympäristökemia
url https://jyx.jyu.fi/handle/123456789/103064 http://www.urn.fi/URN:NBN:fi:jyu-202506044868
work_keys_str_mv AT kangasaliisa calix4pyrrolesinenvironmentalandgreenchemistryapplications