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Stereodifferentiation in the intramolecular singlet excited state quenching of hydroxybiphenyl-tryptophan dyads

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Stereodifferentiation in the intramolecular singlet excited state quenching of hydroxybiphenyl-tryptophan dyads

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dc.contributor.author Bonancía Roca, Paula es_ES
dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Markovitsi, Dimitra es_ES
dc.contributor.author Gustavsson, Thomas es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2016-02-23T09:30:10Z
dc.date.available 2016-02-23T09:30:10Z
dc.date.issued 2013
dc.identifier.issn 1477-0520
dc.identifier.uri http://hdl.handle.net/10251/61108
dc.description.abstract The photochemical processes occurring in diastereomeric dyads (S, S)-1 and (S, R)-1, prepared by conjugation of (S)-2-(2-hydroxy-1,1'-biphenyl-4-yl) propanoic acid ((S)-BPOH) with (S)- and (R)-Trp, have been investigated. In acetonitrile, the fluorescence spectra of (S, S)-1 and (S, R)-1 were coincident in shape and position with that of (S)-BPOH, although they revealed a markedly stereoselective quenching. Since singlet energy transfer from BPOH to Trp is forbidden (5 kcal mol(-1) uphill), the quenching was attributed to thermodynamically favoured (according to Rehm-Weller) electron transfer or exciplex formation. Upon addition of 20% water, the fluorescence quantum yield of (S)-BPOH decreased, while only minor changes were observed for the dyads. This can be explained by an enhancement of the excited state acidity of (S)-BPOH, associated with bridging of the carboxy and hydroxy groups by water, in agreement with the presence of water molecules in the X-ray structure of (S)-BPOH. When the carboxy group was not available for coordination with water, as in the methyl ester (S)-BPOHMe or in the dyads, this effect was prevented; accordingly, the fluorescence quantum yields did not depend on the presence or absence of water. The fluorescence lifetimes in dry acetonitrile were 1.67, 0.95 and 0.46 ns for (S)-BPOH, (S, S)-1 and (S, R)-1, respectively, indicating that the observed quenching is indeed dynamic. In line with the steady-state and time-resolved observations, molecular modelling pointed to a more favourable geometric arrangement of the two interacting chromophores in (S, R)-1. Interestingly, this dyad exhibited a folded conformation in the solid state. es_ES
dc.description.sponsorship Financial support from the Spanish Government (CTQ2010-14882, BES-2008-003314, JCI-2011-09926, PR2011-0581), from the Generalitat Valenciana (Prometeo 2008/090) and from the Universitat Politecnica de Valencia (PAID 05-11, 2766) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation Spanish Government CTQ2010-14882 BES-2008-003314 JCI-2011-09926 PR2011-0581 es_ES
dc.relation Generalitat Valenciana 2008/090 es_ES
dc.relation Universitat Politecnica de Valencia PAID 05-11 2766 es_ES
dc.relation.ispartof Organic and Biomolecular Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject HUMAN SERUM-ALBUMIN es_ES
dc.subject PROTON-TRANSFER es_ES
dc.subject ELECTRON-TRANSFER es_ES
dc.subject THYMINE DYADS es_ES
dc.subject MODEL DYADS es_ES
dc.subject FLUORESCENCE es_ES
dc.subject PROTEINS es_ES
dc.subject FLURBIPROFEN es_ES
dc.subject DRUG es_ES
dc.subject RELAXATION es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Stereodifferentiation in the intramolecular singlet excited state quenching of hydroxybiphenyl-tryptophan dyads es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c3ob27278h
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Bonancía Roca, P.; Vayá Pérez, I.; Markovitsi, D.; Gustavsson, T.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2013). Stereodifferentiation in the intramolecular singlet excited state quenching of hydroxybiphenyl-tryptophan dyads. Organic and Biomolecular Chemistry. 11(12):1958-1963. doi:10.1039/c3ob27278h es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c3ob27278h es_ES
dc.description.upvformatpinicio 1958 es_ES
dc.description.upvformatpfin 1963 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 11 es_ES
dc.description.issue 12 es_ES
dc.relation.senia 234594 es_ES
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