{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/21003"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/21003","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Hydrogen bond mediated self-assembly: Solid state structures and synthesis of building blocks","abstract":"\"The X-ray structure of a trimesic acid$\\bullet$pyrene$\\bullet$ethanol cocrystal is described. The \"\"chicken-wire\"\" network found in trimesic acid was expanded through ethanol bridging of some of the hydrogen bonded carboxylic acid dimers. The expanded chicken wire networks of the structure do not interpenetrate. The Cambridge Crystallographic Data File (CCDF) was searched to determine the ratio of hydroxy bridge carboxylic acids to standard dimers. Standard dimers represented 93%, singly bridged dimers 1%, and doubly bridged dimers 6% of the total number of hits.\"","abstract_html":""The X-ray structure of a trimesic acid$\\bullet$pyrene$\\bullet$ethanol cocrystal is described. The ""chicken-wire"" network found in trimesic acid was expanded through ethanol bridging of some of the hydrogen bonded carboxylic acid dimers. The expanded chicken wire networks of the structure do not interpenetrate. The Cambridge Crystallographic Data File (CCDF) was searched to determine the ratio of hydroxy bridge carboxylic acids to standard dimers. Standard dimers represented 93%, singly bridged dimers 1%, and doubly bridged dimers 6% of the total number of hits."","abstract_has_math":true,"creators":["Fenlon, Edward Emmett"],"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":2011,"date_issued":"2011-05-07T12:55:28Z","date_published":"2011-05-07T12:55:28Z","updated_at":"2026-07-22T22:25:17Z","subjects":["Chemistry, Organic","Chemistry, Physical"],"languages":["eng"],"rights":["Copyright 1995 Fenlon, Edward Emmett"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9624344","(UMI)AAI9624344"],"render_values":[{"text":"AAI9624344","href":null,"code":true},{"text":"(UMI)AAI9624344","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/21003","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":["Fenlon, Edward Emmett"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011-05-07T12:55:28Z","10000-01-01","1995"]},{"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, Physical"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1995 Fenlon, Edward Emmett"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9624344","(UMI)AAI9624344","http://hdl.handle.net/2142/21003"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["\"The X-ray structure of a trimesic acid$\\bullet$pyrene$\\bullet$ethanol cocrystal is described. The \"\"chicken-wire\"\" network found in trimesic acid was expanded through ethanol bridging of some of the hydrogen bonded carboxylic acid dimers. The expanded chicken wire networks of the structure do not interpenetrate. The Cambridge Crystallographic Data File (CCDF) was searched to determine the ratio of hydroxy bridge carboxylic acids to standard dimers. Standard dimers represented 93%, singly bridged dimers 1%, and doubly bridged dimers 6% of the total number of hits.\"","The five step synthesis of bis-guanine 78, potentially capable of forming a helical aggregate with bis-cytosine 88, is described. The X-ray crystal structure of bis-cytosine 88 is presented.","The design and synthesis of 1,7,10-anthyridin-6(7H)-one 123a and pyrido- (3,2-g) -pteridin-4(3H)-one 150, each capable of forming cyclic hydrogen bonded hexamers are described. Several 1,7,10-anthyridines were prepared. The final step in the syntheses was a double ring annulation by a Friedlander-like condensation between 2,6-diaminopyridine-3-carboxaldehyde and methyl 3,5-dioxo-5-amino pentanoate. The synthesis of pyrido- (3,2-g) -pteridin-4(3H)-one 150 required 14 steps and proceeded in 3.3% yield. The convergent step in the synthesis was a Timmis condensation between 6-amino-2-(methylthio)-5-nitroso-pyrimidin-4-one and nitrile 134 to form pterin 146. Preliminary gel permeation chromatography (GPC) studies suggest that 150 forms a discrete aggregate in methylene chloride and tetrahydrofuran.","Made available in DSpace on 2011-05-07T12:55:28Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9624344.pdf: 3950234 bytes, checksum: 1fa51d81134daa51ff8696baaca14237 (MD5) Previous issue date: 1995","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:47:49Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:21:37-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"]},{"key":"dc:title","label":"Title","values":["Hydrogen bond mediated self-assembly: Solid state structures and synthesis of building blocks"]}]}],"canonical_facts":{"dc:contributor":["Zimmerman, Steven C."],"dc:creator":["Fenlon, Edward Emmett"],"dc:date":["2011-05-07T12:55:28Z","10000-01-01","1995"],"dc:description":["\"The X-ray structure of a trimesic acid$\\bullet$pyrene$\\bullet$ethanol cocrystal is described. The \"\"chicken-wire\"\" network found in trimesic acid was expanded through ethanol bridging of some of the hydrogen bonded carboxylic acid dimers. The expanded chicken wire networks of the structure do not interpenetrate. The Cambridge Crystallographic Data File (CCDF) was searched to determine the ratio of hydroxy bridge carboxylic acids to standard dimers. Standard dimers represented 93%, singly bridged dimers 1%, and doubly bridged dimers 6% of the total number of hits.\"","The five step synthesis of bis-guanine 78, potentially capable of forming a helical aggregate with bis-cytosine 88, is described. The X-ray crystal structure of bis-cytosine 88 is presented.","The design and synthesis of 1,7,10-anthyridin-6(7H)-one 123a and pyrido- (3,2-g) -pteridin-4(3H)-one 150, each capable of forming cyclic hydrogen bonded hexamers are described. Several 1,7,10-anthyridines were prepared. The final step in the syntheses was a double ring annulation by a Friedlander-like condensation between 2,6-diaminopyridine-3-carboxaldehyde and methyl 3,5-dioxo-5-amino pentanoate. The synthesis of pyrido- (3,2-g) -pteridin-4(3H)-one 150 required 14 steps and proceeded in 3.3% yield. The convergent step in the synthesis was a Timmis condensation between 6-amino-2-(methylthio)-5-nitroso-pyrimidin-4-one and nitrile 134 to form pterin 146. Preliminary gel permeation chromatography (GPC) studies suggest that 150 forms a discrete aggregate in methylene chloride and tetrahydrofuran.","Made available in DSpace on 2011-05-07T12:55:28Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9624344.pdf: 3950234 bytes, checksum: 1fa51d81134daa51ff8696baaca14237 (MD5) Previous issue date: 1995","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:47:49Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:21:37-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"],"dc:identifier":["AAI9624344","(UMI)AAI9624344","http://hdl.handle.net/2142/21003"],"dc:language":["eng"],"dc:rights":["Copyright 1995 Fenlon, Edward Emmett"],"dc:subject":["Chemistry, Organic","Chemistry, Physical"],"dc:title":["Hydrogen bond mediated self-assembly: Solid state structures and synthesis of building blocks"],"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":"2026-07-22T22:25:17Z"}