{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:49:28Z","timestamp":1760316568186,"version":"build-2065373602"},"reference-count":87,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2006,12,1]],"date-time":"2006-12-01T00:00:00Z","timestamp":1164931200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2007,3,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This article describes two different types of dynamic combinatorial libraries of host and guest molecules. The first part of this article describes the encapsulation of alizarin trimer <jats:bold>2\u2009a<\/jats:bold><jats:sub>3<\/jats:sub> by dynamic mixtures of up to twenty different self\u2010assembled molecular receptors together with the amplification and selection of the best binder. Receptors (<jats:bold>1\u2009a<\/jats:bold>\u2013<jats:bold>d<\/jats:bold>)<jats:sub>3<\/jats:sub><jats:bold>\u22c5<\/jats:bold>(DEB)<jats:sub>6<\/jats:sub> are formed by the self\u2010assembly of six diethyl barbiturate (DEB) and calix[4]arene dimelamine derivatives <jats:bold>1\u2009a<\/jats:bold>\u2013<jats:bold>d<\/jats:bold> by using hydrogen bonds. The largest amplification factor (2.8) for a host assembly (<jats:bold>1\u2009a<\/jats:bold><jats:sub>3<\/jats:sub><jats:bold>\u22c5<\/jats:bold> (DEB)<jats:sub>6<\/jats:sub>) was observed after the addition of <jats:bold>2\u2009a<\/jats:bold> to four\u2010component library <jats:bold>1\u2009a<\/jats:bold><jats:sub><jats:italic>n<\/jats:italic><\/jats:sub><jats:bold>\u22c51\u2009b<\/jats:bold><jats:sub>(3\u2212<jats:italic>n<\/jats:italic>)<\/jats:sub><jats:bold>\u22c5<\/jats:bold>(DEB)<jats:sub>6<\/jats:sub> (<jats:italic>n<\/jats:italic>=0\u20133). Addition of <jats:bold>2\u2009a<\/jats:bold> to twenty\u2010component library <jats:bold>1\u2009a<\/jats:bold><jats:sub><jats:italic>n<\/jats:italic><\/jats:sub><jats:bold>\u22c51\u2009b<\/jats:bold><jats:sub><jats:italic>m<\/jats:italic><\/jats:sub><jats:bold>\u22c51\u2009c<\/jats:bold><jats:sub><jats:italic>o<\/jats:italic><\/jats:sub><jats:bold>\u22c51\u2009d<\/jats:bold><jats:sub>(3\u2212(<jats:italic>n<\/jats:italic>+<jats:italic>m<\/jats:italic>+<jats:italic>o<\/jats:italic>))<\/jats:sub><jats:bold>\u22c5<\/jats:bold>(DEB)<jats:sub>6<\/jats:sub> (<jats:italic>n<\/jats:italic>, <jats:italic>m<\/jats:italic>, <jats:italic>o<\/jats:italic>=0\u20133; (<jats:italic>n<\/jats:italic>+<jats:italic>m<\/jats:italic>+<jats:italic>o<\/jats:italic>)\u22643) also showed amplification of receptor <jats:bold>1\u2009a<\/jats:bold><jats:sub>3<\/jats:sub><jats:bold>\u22c5<\/jats:bold>(DEB)<jats:sub>6<\/jats:sub>. The second part of this article describes the complexation of libraries of different alizarin\u2010like guest molecules (<jats:bold>2\u2009a<\/jats:bold>\u2013<jats:bold>d<\/jats:bold>) and the self\u2010assembled receptor <jats:bold>1\u2009a<\/jats:bold><jats:sub>3<\/jats:sub><jats:bold>\u22c5<\/jats:bold>(DEB)<jats:sub>6<\/jats:sub>. This receptor is able to template the formation of the best\u2010fitting guest trimer.<\/jats:p>","DOI":"10.1002\/chem.200601198","type":"journal-article","created":{"date-parts":[[2006,12,1]],"date-time":"2006-12-01T05:32:07Z","timestamp":1164951127000},"page":"2377-2385","source":"Crossref","is-referenced-by-count":19,"title":["Dynamic Combinatorial Libraries Based on Hydrogen\u2010Bonded Molecular Boxes"],"prefix":"10.1002","volume":"13","author":[{"given":"Jessica\u2005M.\u2005C.\u2005A.","family":"Kerckhoffs","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miguel\u2005A.","family":"Mateos\u2010Timoneda","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"David\u2005N.","family":"Reinhoudt","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mercedes","family":"Crego\u2010Calama","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,2,19]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For examples of combinatorial libraries 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Chem. 2003, 115","first-page":"1308","author":"Brisig B.","key":"e_1_2_6_52_2"},{"key":"e_1_2_6_52_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390326"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.082643499"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1072361"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja005507o"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0351589"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(20000218)112:4<771::AID-ANGE771>3.0.CO;2-7"},{"key":"e_1_2_6_57_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(20000218)39:4<755::AID-ANIE755>3.0.CO;2-6"},{"key":"e_1_2_6_58_2","unstructured":"\u00a0"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0202006"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351623"},{"key":"e_1_2_6_60_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351623"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19970031115"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19961081113"},{"key":"e_1_2_6_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199612151"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352733"},{"key":"e_1_2_6_63_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352733"},{"key":"e_1_2_6_64_2","unstructured":"Here the amplified receptors are considered in principle as the best binders. Nevertheless the amplification could be biased by the concentration of guest see ref.\u2005[9]. Other experiments with different concentrations showed similar results. Furthermore after templation by the guest only homomeric assemblies are formed thus the libraries are not biased by the experimental conditions otherwise the heteromeric assemblies would be preferred see ref.\u2005[9b]."},{"key":"e_1_2_6_65_2","unstructured":"In general the signals observed in this solvent are sharper than those in CDCl3. The shifts of the1H\u2005NMR signals for the encapsulation of2\u2009aby1\u2009a3\u22c5(DEB)6in [D8]toluene differ slightly from those observed in CDCl3."},{"key":"e_1_2_6_66_2","unstructured":"The signal labeled \u25aa in Figure\u20058b clearly comes from the homomeric complex1\u2009a3\u22c5(DEB)6\u22c52\u2009a3as shown by the1H\u2005NMR spectrum of the individual assembly (Figure\u20058c). Integration of the signals reveals that those labeled with \u25b4 belong to one complex and those labeled with \u25b5 belong to another complex. The fact that three signals belong to one complex mean that these are heteromeric assemblies that give separate signals for each OHn. The signals labeled with \u25b4 probably belong to complex1\u2009a2\u22c51\u2009c1\u22c5(DEB)6\u22c52\u2009a3when considering that OHnprotons closer to calix[4]arene melamine1\u2009aresonate at\u03b4=>10.0\u2005ppm and the that OHnprotons closer to calix[4]arene melamine1\u2009cresonate at\u03b4=<9.9\u2005ppm. By applying the same reasoning the signals labeled with \u25b5 belong to complex1\u2009a1\u22c51\u2009c2\u22c5(DEB)6\u22c52\u2009a3. Consequently it seems that calix[4]arene dimelamine1\u2009cin the dynamic mixture forms heteromeric complexes that are similar to complex1\u2009a3\u22c5(DEB)6\u22c52\u2009a3."},{"key":"e_1_2_6_67_2","unstructured":"See theSupporting Informationfor similar results obtained after addition of2\u2009ato DCL1\u2009a2\u22c51\u2009d1\u22c5(DEB)6."},{"key":"e_1_2_6_68_2","unstructured":"As previously published this receptor can template the formation of noncovalent trimers2\u2009a3and2\u2009b3(see ref.\u2005[17])."},{"key":"e_1_2_6_69_2","unstructured":"Complex1\u2009a3\u22c5(DEB)6\u22c52\u2009b3does not contain the OHmproton and therefore the abundance of this complex could not be determined by the integration of this signal. Integration of the OHnsignals is difficult because these signals partially overlap."},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3757(19980504)110:9<1294::AID-ANGE1294>3.0.CO;2-Z"},{"key":"e_1_2_6_70_3","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1521-3773(19980518)37:9<1247::AID-ANIE1247>3.0.CO;2-7"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3765(20001117)6:22<4104::AID-CHEM4104>3.0.CO;2-Q"},{"key":"e_1_2_6_72_2","unstructured":"The amount of2\u2009dweighed was 3.8\u2005equiv but not all material dissolved in CDCl3."},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1039\/a909459h"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.200601198","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.200601198","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:49:56Z","timestamp":1760287796000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.200601198"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2007,2,19]]},"references-count":87,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2007,3,5]]}},"alternative-id":["10.1002\/chem.200601198"],"URL":"https:\/\/doi.org\/10.1002\/chem.200601198","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2007,2,19]]}}}