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dc.contributor.author
Moore, Gary F.
dc.contributor.author
Megiatto, Jackson D.
dc.contributor.author
Hambourger, Michael
dc.contributor.author
Gervaldo, Miguel Andres
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dc.contributor.author
Kodis, Gerdenis
dc.contributor.author
Moore, Thomas A.
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Gust, Devens
dc.contributor.author
Moore, Ana L.
dc.date.available
2023-05-31T18:00:53Z
dc.date.issued
2012-06
dc.identifier.citation
Moore, Gary F.; Megiatto, Jackson D.; Hambourger, Michael; Gervaldo, Miguel Andres; Kodis, Gerdenis; et al.; Optical and electrochemical properties of hydrogen-bonded phenol-pyrrolidino[60]fullerenes; Royal Society of Chemistry; Photochemical and Photobiological Sciences; 11; 6; 6-2012; 1018-1025
dc.identifier.issn
1474-905X
dc.identifier.uri
http://hdl.handle.net/11336/199190
dc.description.abstract
We report the photophysical and electrochemical properties of phenol-pyrrolidino[60]fullerenes 1 and 2, in which the phenol hydroxyl group is ortho and para to the pyrrolidino group, respectively, as well as those of a phenyl-pyrrolidino[60]fullerene model compound, 3. For the ortho analog 1, the presence of an intramolecular hydrogen bond is supported by 1H NMR and FTIR characterization. The redox potential of the phenoxyl radical-phenol couple in this architecture is 240 mV lower than that observed in the associated para compound 2. Further, the C60 excited-state lifetime of the hydrogen-bonded compound 1 in benzonitrile is 260 ps, while the corresponding lifetime for 2 is identical to that of the model compound 3 at 1.34 ns. Addition of excess organic acid to a benzonitrile solution of 1 gives rise to a new species, 4, with an excited-state lifetime of 1.40 ns. In nonpolar aprotic solvents such as toluene, all three compounds have a C60 excited-state lifetime of ∼1 ns. These results suggest that the presence of an intramolecular H-bond in 1 poises the potential of phenoxyl radical-phenol redox couple at a value that it is thermodynamically capable of reducing the photoexcited fullerene. This is not the case for the para analog 2 nor is it the case for the protonated species 4. This work illustrates that in addition to being used as light activated electron acceptors, pyrrolidino fullerenes are also capable of acting as built-in proton-accepting units that influence the potential of an attached donor when organized in an appropriate molecular design.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Photosystem II
dc.subject
Fullerene
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Optical and electrochemical properties of hydrogen-bonded phenol-pyrrolidino[60]fullerenes
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2023-05-30T11:50:19Z
dc.identifier.eissn
1474-9092
dc.journal.volume
11
dc.journal.number
6
dc.journal.pagination
1018-1025
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Cambridge
dc.description.fil
Fil: Moore, Gary F.. Lawrence Berkeley National Laboratory; Estados Unidos. Arizona State University; Estados Unidos
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Fil: Megiatto, Jackson D.. Arizona State University; Estados Unidos
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Fil: Hambourger, Michael. Arizona State University; Estados Unidos. Appalachian State University (appstate);
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Fil: Gervaldo, Miguel Andres. Arizona State University; Estados Unidos. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados. - Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Tecnologías Energéticas y Materiales Avanzados; Argentina
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Fil: Kodis, Gerdenis. Arizona State University; Estados Unidos
dc.description.fil
Fil: Moore, Thomas A.. Arizona State University; Estados Unidos
dc.description.fil
Fil: Gust, Devens. Arizona State University; Estados Unidos
dc.description.fil
Fil: Moore, Ana L.. Arizona State University; Estados Unidos
dc.journal.title
Photochemical and Photobiological Sciences
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org//10.1039/c2pp05351a
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://link.springer.com/article/10.1039/c2pp05351a#citeas
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