{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/77259"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/77259","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Part I: Rapid Synthesis of Dendrimers by an Orthogonal Coupling Strategy. Part II: Design, Synthesis, and Characterization of Hydrogen-Bond Mediated Self-Assembling Dendrimers","abstract":"Part I. Layered dendrimers were rapidly synthesized using an orthogonal coupling strategy. Fourth generation dendron 71 was prepared in four steps by sequential use of two AB$\\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula $\\rm C\\sb{1292}H\\sb{1369}IO\\sb{242}$ and a molecular weight of 20897 amu, was synthesized in just three steps from the corresponding AB$\\sb4$ monomers 72 and 73. In comparison to the most efficient dendrimer synthesis available, the orthogonal coupling strategy halves the number of synthetic steps needed by obviating protection-deprotection and activation chemistry.","abstract_html":"Part I. Layered dendrimers were rapidly synthesized using an orthogonal coupling strategy. Fourth generation dendron 71 was prepared in four steps by sequential use of two AB$\\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula $\\rm C\\sb{1292}H\\sb{1369}IO\\sb{242}$ and a molecular weight of 20897 amu, was synthesized in just three steps from the corresponding AB$\\sb4$ monomers 72 and 73. In comparison to the most efficient dendrimer synthesis available, the orthogonal coupling strategy halves the number of synthetic steps needed by obviating protection-deprotection and activation chemistry.","abstract_has_math":true,"creators":["Zeng, Fanwen"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Zimmerman, Steven C."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-05-13T15:37:29Z","date_published":"2015-05-13T15:37:29Z","updated_at":"2026-07-22T22:26:10Z","subjects":["Chemistry, Organic","Chemistry, Polymer"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI9737300"],"render_values":[{"text":"(UMI)AAI9737300","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/77259","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Zimmerman, Steven C."]},{"key":"dc:creator","label":"Author","values":["Zeng, Fanwen"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-05-13T15:37:29Z","10000-01-01","1997"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic","Chemistry, Polymer"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/77259","(UMI)AAI9737300"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Part I. Layered dendrimers were rapidly synthesized using an orthogonal coupling strategy. Fourth generation dendron 71 was prepared in four steps by sequential use of two AB$\\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula $\\rm C\\sb{1292}H\\sb{1369}IO\\sb{242}$ and a molecular weight of 20897 amu, was synthesized in just three steps from the corresponding AB$\\sb4$ monomers 72 and 73. In comparison to the most efficient dendrimer synthesis available, the orthogonal coupling strategy halves the number of synthetic steps needed by obviating protection-deprotection and activation chemistry.","Part II. Discrete aggregates with a size in the nano-scale were formed by the hydrogen-bond mediated self-assembly of dendritic macromolecules. Several hydrogen bonding units were investigated, including anthyridine and diaminodihydropyridine moieties that are complementary (AAA-DDD), and self-complementary isophthalic acid, and 6-aminonicotinic acid subunits. Among them, dendritic tetraacids 189a-d were shown to self-assemble in a generation-dependent manner. The lower generation tetraacid 189a prefers to form a series of linear aggregates, while the higher generation tetraacids 189b-d tend to form a cyclic hexamer. The observation was supported by SEC dilution studies, VPO, and comparison with covalent models 208a-c.","Made available in DSpace on 2015-05-13T15:37:29Z (GMT). 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Layered dendrimers were rapidly synthesized using an orthogonal coupling strategy. Fourth generation dendron 71 was prepared in four steps by sequential use of two AB$\\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula $\\rm C\\sb{1292}H\\sb{1369}IO\\sb{242}$ and a molecular weight of 20897 amu, was synthesized in just three steps from the corresponding AB$\\sb4$ monomers 72 and 73. In comparison to the most efficient dendrimer synthesis available, the orthogonal coupling strategy halves the number of synthetic steps needed by obviating protection-deprotection and activation chemistry.","Part II. Discrete aggregates with a size in the nano-scale were formed by the hydrogen-bond mediated self-assembly of dendritic macromolecules. Several hydrogen bonding units were investigated, including anthyridine and diaminodihydropyridine moieties that are complementary (AAA-DDD), and self-complementary isophthalic acid, and 6-aminonicotinic acid subunits. Among them, dendritic tetraacids 189a-d were shown to self-assemble in a generation-dependent manner. The lower generation tetraacid 189a prefers to form a series of linear aggregates, while the higher generation tetraacids 189b-d tend to form a cyclic hexamer. The observation was supported by SEC dilution studies, VPO, and comparison with covalent models 208a-c.","Made available in DSpace on 2015-05-13T15:37:29Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 9737300.PDF: 8844152 bytes, checksum: 9c5e0c6d0fc5919ba1f49e2be7d0e02c (MD5) Previous issue date: 1997","Embargo set by: Seth Robbins for item 78470 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","220 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1997."],"dc:identifier":["http://hdl.handle.net/2142/77259","(UMI)AAI9737300"],"dc:language":["eng"],"dc:subject":["Chemistry, Organic","Chemistry, Polymer"],"dc:title":["Part I: Rapid Synthesis of Dendrimers by an Orthogonal Coupling Strategy. Part II: Design, Synthesis, and Characterization of Hydrogen-Bond Mediated Self-Assembling Dendrimers"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:10Z"}