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Four generations of Hamilton\u2010receptor\u2010functionalized dendrimers (HR\u2010dendrimers) were synthesized and characterized by <jats:sup>1<\/jats:sup>H and <jats:sup>13<\/jats:sup>C NMR spectroscopy and MALDI\u2010TOF mass spectrometry. The photophysical properties of the HR\u2010dendrimers were investigated by UV\/Vis as well as with steady\u2010state and time\u2010resolved fluorescence spectroscopy. The dendrimers were used as multivalent hosts for the barbiturate guests Barbital (<jats:bold>7<\/jats:bold>) and [Re(Br)(CO)<jats:sub>3<\/jats:sub>(barbi\u2010bpy)] (<jats:bold>8<\/jats:bold>; barbi\u2010bpy=5\u2010[4\u2010(4\u2032\u2010methyl)\u20102,2\u2032\u2010bipyridyl]methyl\u20102,4,6\u2010(1\u2009<jats:italic>H<\/jats:italic>,3\u2009<jats:italic>H<\/jats:italic>,5\u2009<jats:italic>H<\/jats:italic>)\u2010pyrimidinetrione). The stable adducts formed between the dendritic architectures (the hosts) and the barbiturate guests <jats:bold>7<\/jats:bold> and <jats:bold>8<\/jats:bold> were investigated by <jats:sup>1<\/jats:sup>H NMR spectroscopy and photophysical methods. The binding constants of the barbiturate guests for binding to reference compound <jats:bold>2<\/jats:bold> (with a single receptor unit) in chloroform were found to be 1.4\u00d710<jats:sup>3<\/jats:sup>\u2009<jats:sc>M<\/jats:sc><jats:sup>\u22121<\/jats:sup> and 1.5\u00d710<jats:sup>5<\/jats:sup>\u2009<jats:sc>M<\/jats:sc><jats:sup>\u22121<\/jats:sup> for <jats:bold>7<\/jats:bold> and <jats:bold>8<\/jats:bold>, respectively. Binding of <jats:bold>7<\/jats:bold> to the dendrimers enhances the weak emission of the Hamilton receptor. This increase in emission is also generation dependent; it was found to be most pronounced in the case of <jats:bold>2<\/jats:bold> and the least in the case of the fourth\u2010generation dendrimer <jats:bold>6<\/jats:bold>. The unexpected increase in the quantum yield of emission from the HR\u2010dendrimers with increasing generation could be caused by the rather rigid conformation of the Hamilton receptors in later\u2010generation compounds, which is a result of intramolecular aggregation and steric hindrance at the periphery of the dendrimer. The photoinduced energy transfer from the excited state of the HR\u2010dendrimers to the lower\u2010lying excited state of the guest <jats:bold>8<\/jats:bold> was used to probe the formation of host\u2013guest complexes. The rate of energy transfer was calculated to be 3.6\u00d710<jats:sup>10<\/jats:sup> s<jats:sup>\u22121<\/jats:sup>. Energy transfer in <jats:bold>2<\/jats:bold>\u2282<jats:bold>8<\/jats:bold> only occurred in the presence of a strong base, which shows that the basic amine core in the HR\u2010dendrimers is crucial for this photoinduced process. The binding of <jats:bold>8<\/jats:bold> to the dendrimers is completely reversible: <jats:bold>8<\/jats:bold> can be exchanged with a competitive guest such as <jats:bold>7<\/jats:bold> and the emission of the HR\u2010dendrimer is restored.<\/jats:p>","DOI":"10.1002\/chem.200305461","type":"journal-article","created":{"date-parts":[[2004,4,7]],"date-time":"2004-04-07T13:03:58Z","timestamp":1081343038000},"page":"2036-2047","source":"Crossref","is-referenced-by-count":84,"title":["Multiple Recognition of Barbiturate Guests by \u201cHamilton\u2010Receptor\u201d\u2010Functionalized Dendrimers"],"prefix":"10.1002","volume":"10","author":[{"given":"Anouk","family":"Dirksen","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Uwe","family":"Hahn","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frank","family":"Schwanke","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Nieger","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joost N. H.","family":"Reek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fritz","family":"V\u00f6gtle","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luisa","family":"De Cola","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2004,4,7]]},"reference":[{"key":"e_1_2_6_1_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1071063"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1069197"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527618248.ch41"},{"key":"e_1_2_6_4_2","volume-title":"Supramolecular Chemistry","year":"1991"},{"key":"e_1_2_6_5_2","first-page":"1","volume-title":"Advances in Supramolecular Chemistry","author":"Hamilton A. 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