Publication
An aminonaphthalimide-putrescine conjugate as fluorescent probe for cucurbituril host-guest complexes
| dc.contributor.author | Carvalho, Cátia Parente | |
| dc.contributor.author | Ferreira, Rita | |
| dc.contributor.author | Silva, José P. da | |
| dc.contributor.author | Pischel, Uwe | |
| dc.date.accessioned | 2015-06-22T14:13:49Z | |
| dc.date.available | 2015-06-22T14:13:49Z | |
| dc.date.issued | 2013 | |
| dc.description.abstract | A fluorophore-anchor dye based on the 4-amino-1,8-naphthalimide chromophore was designed and characterised with respect to its ability of forming supramolecular hostguest complexes with cucurbit[6]uril (CB6) and cucurbit[7]uril (CB7) hosts. It was found that CB6 encapsulates the anchor of the dye with a high binding constant [K = (1.11.4) X 107 M- 1], which was independent of acidic or neutral pH conditions. The 1:1 binding was accompanied by fluorescence quenching (ca. 20%) and a bathochromic shift (?? = +22 nm) of the charge-transfer absorption band of the dye. This is indicative of the occurrence of hydrogen bonding between a carbonyl-lined host portal and the aromatic NH group of the guest dye. In comparison, CB7 encapsulated the dye much less efficiently (K = 4.8 X 104 M- 1) and showed a significant fluorescence enhancement (Ff = 0.15 versus 0.52 for free and CB7-complexed dye at pH 4, respectively). The occurrence of hydrogen bonding with the aromatic NH was much less evident for CB7 as judged by the only minor bathochromic shift (?? = +4 nm) of the charge-transfer absorption band of the dye. The dyeCB6 assembly has the potential for the detection of biogenic amines under physiological pH conditions and at low analyte concentrations. | |
| dc.identifier.doi | https://dx.doi.org/10.1080/10610278.2012.726732 | |
| dc.identifier.issn | 1061-0278 | |
| dc.identifier.uri | http://hdl.handle.net/10400.1/6554 | |
| dc.language.iso | eng | |
| dc.peerreviewed | yes | |
| dc.publisher | Taylor & Francis | |
| dc.relation.isbasedon | P-002-11M | |
| dc.subject | Fluorescence | |
| dc.subject | Charge transfer | |
| dc.subject | Hydrogen bonding | |
| dc.subject | Cucurbituril | |
| dc.subject | Host–guest chemistry | |
| dc.title | An aminonaphthalimide-putrescine conjugate as fluorescent probe for cucurbituril host-guest complexes | |
| dc.type | journal article | |
| dspace.entity.type | Publication | |
| oaire.citation.endPage | 100 | |
| oaire.citation.issue | 2 | |
| oaire.citation.startPage | 92 | |
| oaire.citation.title | Supramolecular Chemistry | |
| oaire.citation.volume | 25 | |
| person.familyName | Da Silva | |
| person.givenName | José Paulo | |
| person.identifier.ciencia-id | 3413-C4F4-73F7 | |
| person.identifier.orcid | 0000-0002-6458-7328 | |
| person.identifier.rid | A-4606-2008 | |
| person.identifier.scopus-author-id | 7201733236 | |
| rcaap.rights | restrictedAccess | |
| rcaap.type | article | |
| relation.isAuthorOfPublication | e2004fa2-a47d-44b0-b11c-fc95fe51cbf9 | |
| relation.isAuthorOfPublication.latestForDiscovery | e2004fa2-a47d-44b0-b11c-fc95fe51cbf9 |
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