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AuthorXu, Youzhidc.contributor.author
Date of accession2019-12-18T16:20:15Zdc.date.accessioned
Available in OPARU since2019-12-18T16:20:15Zdc.date.available
Year of creation2019dc.date.created
Date of first publication2019-12-18dc.date.issued
AbstractThe central goal of this thesis was to tackle the challenging synthesis of strained carbon nanohoops and explore their applications in supramolecular chemistry as well as material science. Strained carbon nanohoops are macrocycles whose backbones are comprised only of sp2- and/or sp-hybridized carbon atoms and that are particularly shape-persistent. [n]Cycloparaphenylene-acetylenes ([n]CPPAs) and [n]cycloparaphenylenes ([n]CPPs) are the most prominent examples of strained carbon nanohoops that are synthetically accessible. Following a decade of rapid progress on the synthesis of nanohoops, the research interest is shifting towards investigations of their properties and applications. [10]CPP is undoubtedly one of the most interesting family members of [n]CPPs, because it has a perfect ring size for the strong concave–convex π–π interaction with C60/C70. Therefore, the work of this thesis is focused on unleashing the supramolecular potential of [10]CPP derivatives and analogues. The first chapter of this thesis introduces nonplanar π-conjugated systems, and mainly focuses on the synthesis and supramolecular chemistry of strained carbon nanohoops (the last of these topics is presented in the form of a review article, which was recently published in Angewandte Chemie). Chapter 2 is a synopsis on the aims and achievements of each of the three research projects that have been carried out (Figure 1). Chapter 3 is presented in the form of articles that have recently been published or are under peer-review. Section 3.1 (Project I) describes the synthesis of two new [2]rotaxanes featuring [10]CPP. In these mechanically interlocked architectures, [10]CPP served as a supramolecular directing group to improve the regioselectivity of fullerene bisaddition. Section 3.2 (Project II) deals with an efficient modular electron transport system, in which [10]CPP plays the role of a rigid non-covalent bridge between zinc porphyrin and a range of fullerenes. Section 3.3 (Project III) presents the synthesis, optoelectronic properties and fullerene affinity of a series of highly strained porphyrinylene nanohoops ([10]CPP analogues). Chapter 4 contains closing remarks about the scope and significance of the presented work as well as further ideas that are currently being tested in the Delius lab.dc.description.abstract
Languageendc.language.iso
PublisherUniversität Ulmdc.publisher
Articles in publ.Xu, Y.; Gsänger, S.; Minameyer, M. B.; Schwer, F.; Shyshov, O.; Drewello, T.; Meyer, B.; von Delius, M.* Highly Strained, Radially π-Conjugated Porphyrinylene Nanohoops. J. Am. Chem. Soc. 2019, 141, 18500-18507dc.relation.haspart
Articles in publ.Xu, Y.; Kaur, R.; Wang, B.; Minameyer, M. B.; Gsänger, S.; Meyer, B.; Drewello, T.; Guldi, D. M.*; von Delius, M.* Concave-Convex π-π Template Approach Enables the Synthesis of [10]Cycloparaphenylene- Fullerene [2]Rotaxanes. J. Am. Chem. Soc. 2018, 140, 13413–13420.dc.relation.haspart
Articles in publ.Xu, Y.; Wang, B.; Kaur, R.; Minameyer, M. B; Bothe, M.; Drewello, T.; Guldi, D. M.*; von Delius, M.* A Supramolecular [10]CPP Junction Enables Efficient Electron Transfer in Modular Porphyrin- [10]CPP-Fullerene Complexes. Angew. Chem., Int. Ed. 2018, 57, 11549–11553.dc.relation.haspart
Articles in publ.Xu, Y.; von Delius, M.* The Supramolecular Chemistry of Nanohoops Angew. Chem., Int. Ed. 2019, 58, DOI: 10.1002/anie.201906069.dc.relation.haspart
LicenseStandarddc.rights
Link to license texthttps://oparu.uni-ulm.de/xmlui/license_v3dc.rights.uri
KeywordCycloparaphenylenedc.subject
KeywordStrained carbon nanohoopsdc.subject
KeywordPorphyrinylenedc.subject
Dewey Decimal GroupDDC 540 / Chemistry & allied sciencesdc.subject.ddc
LCSHRotaxanesdc.subject.lcsh
LCSHFullerenesdc.subject.lcsh
TitleSynthesis and supramolecular chemistry of strained carbon nanohoopsdc.title
Resource typeDissertationdc.type
Date of acceptance2019-11-18dcterms.dateAccepted
Refereevon Delius, Maxdc.contributor.referee
RefereeKühne, Alexanderdc.contributor.referee
DOIhttp://dx.doi.org/10.18725/OPARU-23305dc.identifier.doi
PPN168595362Xdc.identifier.ppn
URNhttp://nbn-resolving.de/urn:nbn:de:bsz:289-oparu-23368-3dc.identifier.urn
GNDRotaxanedc.subject.gnd
GNDFullerenedc.subject.gnd
FacultyFakultät für Naturwissenschaftenuulm.affiliationGeneral
InstitutionInstitut für Organische Chemie Iuulm.affiliationSpecific
InstitutionInstitut für Organische Chemie III (Makromolekulare Chemie und Organische Materialien)uulm.affiliationSpecific
Grantor of degreeFakultät für Naturwissenschaftenuulm.thesisGrantor
DCMI TypeTextuulm.typeDCMI
CategoryPublikationenuulm.category
FundingSFB 953 / Synthetische Kohlenstoffallotrope / DFG / SFB / 182849149uulm.funding
University Bibliographyjauulm.unibibliographie


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