{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/22668"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/22668","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Studies in molecular recognition. Part I. Expanded molecular tweezers: Design and synthesis of novel receptors. Part II. Molecular self-assembly: Use of carboxylic acids as self-assembly elements","abstract":"In Part I, the design, synthetic approaches, and complexation studies of molecular tweezers possessing spacer units $>$7 A are discussed. A general feature of these approaches is the use of the Friedlander reaction to generate the spacer unit. A tweezer utilizing 2,7-dimethoxyacridine as the chromophore with an inter-chromophore distance of 9.7 A was synthesized. This expanded tweezer was found to bind 2,4,5,7-tetranitrofluorenone (TENF) with a K$\\sb{\\rm a}$ $<$ 10 M$\\sp{-1}$. Progress in the synthesis of a water soluble tweezer with an expanded spacer unit is also reported.","abstract_html":"In Part I, the design, synthetic approaches, and complexation studies of molecular tweezers possessing spacer units $&gt;$7 A are discussed. A general feature of these approaches is the use of the Friedlander reaction to generate the spacer unit. A tweezer utilizing 2,7-dimethoxyacridine as the chromophore with an inter-chromophore distance of 9.7 A was synthesized. This expanded tweezer was found to bind 2,4,5,7-tetranitrofluorenone (TENF) with a K$\\sb{\\rm a}$ $&lt;$ 10 M$\\sp{-1}$. Progress in the synthesis of a water soluble tweezer with an expanded spacer unit is also reported.","abstract_has_math":true,"creators":["Reichert, David Edward Caples"],"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":1994,"date_issued":"1994","date_published":"1994","updated_at":"2026-07-22T22:25:20Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":["Copyright 1994 Reichert, David Edward Caples"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9512525","(UMI)AAI9512525"],"render_values":[{"text":"AAI9512525","href":null,"code":true},{"text":"(UMI)AAI9512525","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/22668","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":["Reichert, David Edward Caples"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1994","2011-05-07T13:47:27Z","10000-01-01"]},{"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"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1994 Reichert, David Edward Caples"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9512525","(UMI)AAI9512525","http://hdl.handle.net/2142/22668"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["In Part I, the design, synthetic approaches, and complexation studies of molecular tweezers possessing spacer units $>$7 A are discussed. A general feature of these approaches is the use of the Friedlander reaction to generate the spacer unit. A tweezer utilizing 2,7-dimethoxyacridine as the chromophore with an inter-chromophore distance of 9.7 A was synthesized. This expanded tweezer was found to bind 2,4,5,7-tetranitrofluorenone (TENF) with a K$\\sb{\\rm a}$ $<$ 10 M$\\sp{-1}$. Progress in the synthesis of a water soluble tweezer with an expanded spacer unit is also reported.","In Part II, the design and synthesis of a novel molecular tweezer which utilizes carboxylic acids as self-assembly elements is reported. The key feature of the synthesis was the Suzuki coupling of the bis(boronic acid) derived from 2,12-dibromo-7-(4$ \\sp\\prime$-methoxyphenyl)-5,6,8,9-tetrahydro-dibenz (c, h) acridine and 5-methylisophthalate triflate. The addition of a solubilizing group and hydrolysis of the methyl esters gave a molecular tweezer with four carboxylic acids which was soluble in organic solvents. Preliminary investigations suggest that the tweezer forms a well-defined aggregate in CH$\\sb2$Cl$\\sb2$.","Made available in DSpace on 2011-05-07T13:47:27Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9512525.pdf: 3602490 bytes, checksum: 3ba37e4b5171c4153f9dd2933a9a5046 (MD5) Previous issue date: 1994","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:59:11Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:27:53-05:00 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":["Studies in molecular recognition. Part I. Expanded molecular tweezers: Design and synthesis of novel receptors. Part II. Molecular self-assembly: Use of carboxylic acids as self-assembly elements"]}]}],"canonical_facts":{"dc:contributor":["Zimmerman, Steven C."],"dc:creator":["Reichert, David Edward Caples"],"dc:date":["1994","2011-05-07T13:47:27Z","10000-01-01"],"dc:description":["In Part I, the design, synthetic approaches, and complexation studies of molecular tweezers possessing spacer units $>$7 A are discussed. A general feature of these approaches is the use of the Friedlander reaction to generate the spacer unit. A tweezer utilizing 2,7-dimethoxyacridine as the chromophore with an inter-chromophore distance of 9.7 A was synthesized. This expanded tweezer was found to bind 2,4,5,7-tetranitrofluorenone (TENF) with a K$\\sb{\\rm a}$ $<$ 10 M$\\sp{-1}$. Progress in the synthesis of a water soluble tweezer with an expanded spacer unit is also reported.","In Part II, the design and synthesis of a novel molecular tweezer which utilizes carboxylic acids as self-assembly elements is reported. The key feature of the synthesis was the Suzuki coupling of the bis(boronic acid) derived from 2,12-dibromo-7-(4$ \\sp\\prime$-methoxyphenyl)-5,6,8,9-tetrahydro-dibenz (c, h) acridine and 5-methylisophthalate triflate. The addition of a solubilizing group and hydrolysis of the methyl esters gave a molecular tweezer with four carboxylic acids which was soluble in organic solvents. Preliminary investigations suggest that the tweezer forms a well-defined aggregate in CH$\\sb2$Cl$\\sb2$.","Made available in DSpace on 2011-05-07T13:47:27Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9512525.pdf: 3602490 bytes, checksum: 3ba37e4b5171c4153f9dd2933a9a5046 (MD5) Previous issue date: 1994","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:59:11Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:27:53-05:00 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":["AAI9512525","(UMI)AAI9512525","http://hdl.handle.net/2142/22668"],"dc:language":["eng"],"dc:rights":["Copyright 1994 Reichert, David Edward Caples"],"dc:subject":["Chemistry, Organic"],"dc:title":["Studies in molecular recognition. Part I. Expanded molecular tweezers: Design and synthesis of novel receptors. Part II. Molecular self-assembly: Use of carboxylic acids as self-assembly elements"],"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":"2026-07-22T22:25:20Z"}