Covalent functionalization of single-walled carbon nanotubes by Bingel reaction for building charge-transfer complexes
dc.contributor.author
dc.date.accessioned
2020-11-19T12:00:21Z
dc.date.available
2022-10-28T05:46:31Z
dc.date.issued
2020-09-18
dc.identifier.issn
0022-3263
dc.identifier.uri
dc.description.abstract
Functionalization of nanotubes with donor and acceptor partners by the Bingel reaction leads to formation of charge-transfer dyads, which can operate in organic photovoltaic devices. In this work, we theoretically examine the mechanism of the Bingel reaction for (6,5)-chiral, (5,5)-armchair, and (9,0)-zig-zag single-walled carbon nanotubes (SWCNTs), and demonstrate that the reaction is regioselective and takes place at the perpendicular position of (6,5)- and (5,5)-SWCNTs, and oblique position of (9,0)-SWCNT. Further, we design computationally the donor-acceptor complexes based on (6,5)-SWCNT coupled with partners of different electronic nature. Analysis of their excited states reveals that efficient photoinduced charge transfer can be achieved in the complexes with exTTF, ZnTPP, and TCAQ. The solvent can significantly affect the population of the charge separated states. Our calculations show that electron transfer (ET) occurs in normal Marcus regime on sub-nanosecond time scale in the complexes with exTTF and ZnTPP, and in inverted Marcus regime on picosecond time scale in the case of TCAQ derivative. The ET rate is found to be not very sensitive to the degree of functionalization of the nanotube
dc.description.sponsorship
We are grateful for financial support from the Spanish MINECO (project CTQ2017‐85341‐P and Juan de la Cierva formación contracts FJCI‐2016‐29448 to A.J.S. and FJCI‐2017‐32757 to O.A.S.), and the Catalan DIUE (2017SGR39). O.A.S and M.S thankfully acknowledge the computer resources at MareNostrum and the technical support provided by Barcelona Supercomputing Center (RES-QS-2019-2-0016)
dc.format.extent
11 p.
dc.format.mimetype
application/pdf
dc.language.iso
eng
dc.publisher
American Chemical Society (ACS)
dc.relation
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P/ES/AVANCES EN LA REACTIVIDAD DE FULLERENOS Y NANOTUBOS: ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION/
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Versió postprint del document publicat a: https://doi.org/10.1021/acs.joc.0c01384
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© Journal of Organic Chemistry, 2020, vol. 85, núm. 18, p. 11721-11731
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.source
Stasyuk, Olga A. Stasyuk, Anton J. Voityuk, Alexander A. Solà i Puig, Miquel 2020 Covalent functionalization of single-walled carbon nanotubes by Bingel reaction for building charge-transfer complexes Journal of Organic Chemistry 85 18 11721 11731
dc.subject
dc.title
Covalent functionalization of single-walled carbon nanotubes by Bingel reaction for building charge-transfer complexes
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
2021-09-18T00:00:00Z
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2021-09-18
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
032145
dc.contributor.funder
dc.type.peerreviewed
peer-reviewed
dc.relation.FundingProgramme
dc.relation.ProjectAcronym
dc.identifier.eissn
1520-6904