Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation

Georgios Rotas; Luis Martín-Gomis; Kei Ohkubo; Fernando Fernández-Lázaro; Shunichi Fukuzumi; Nikos Tagmatarchis; Ángela Sastre-Santos

doi:10.1002/chem.201603065

Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation

Georgios Rotas, Luis Martín-Gomis, Kei Ohkubo, Fernando Fernández-Lázaro, Shunichi Fukuzumi, Nikos Tagmatarchis, Ángela Sastre-Santos

Department of Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

The synthesis of a donor–acceptor silicon phthalocyanine (SiPc)-azafullerene (C₅₉N) dyad 1 and of the first acceptor–donor–acceptor C₅₉N-SiPc-C₅₉N dumbbell triad 2 was accomplished. The two C₅₉N-based materials were comprehensively characterized with the aid of NMR spectroscopy, MALDI-MS as well as DFT calculations and their redox and photophysical properties were evaluated with CV and steady-state and time-resolved absorption and photoluminescence spectroscopy measurements. Notably, femtosecond transient absorption spectroscopy assays revealed that both dyad 1 and triad 2 undergo, after selective photoexcitation of the SiPc moiety, photoinduced electron transfer from the singlet excited state of the SiPc moiety to the azafullerene counterpart to produce the charge-separated state, with lifetimes of 660 ps, in the case of dyad 1, and 810 ps, in the case of triad 2. The current results are expected to have significant implications en route to the design of advanced C₅₉N-based donor–acceptor systems targeting energy conversion applications.

Original language	English
Pages (from-to)	15137-15143
Number of pages	7
Journal	Chemistry - A European Journal
Volume	22
Issue number	42
DOIs	https://doi.org/10.1002/chem.201603065
State	Published - 10 Oct 2016

Bibliographical note

Funding Information:
This research was financially supported by the General Secretariat for Research and Technology and European Commission, through the European Fund for Regional Development, 2007–2013 action “Development of Research Centres-ΚΡΗΠΙΣ”, project 447963 “New Multifunctional Nanostructured Materials and Devices - POLYNANO” (to N.T.), the Spanish Ministry of Economy and Competitiveness (Mineco) of Spain (CTQ2014-55798-R), Generalitat Valenciana (Prometeo 2012/010) and by JSPS KAKENHI (no. 16H02268 to S.F., nos. 16K13964, 26620154 and 26288037 to K.O.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT); SENTAN projects from JST, Japan (to S.F.).

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

azafullerene
donor–acceptor systems
materials science
photoinduced electron transfer
silicon phthalocyanine

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10.1002/chem.201603065

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Rotas, G., Martín-Gomis, L., Ohkubo, K., Fernández-Lázaro, F., Fukuzumi, S., Tagmatarchis, N., & Sastre-Santos, Á. (2016). Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation. Chemistry - A European Journal, 22(42), 15137-15143. https://doi.org/10.1002/chem.201603065

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title = "Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation",

abstract = "The synthesis of a donor–acceptor silicon phthalocyanine (SiPc)-azafullerene (C59N) dyad 1 and of the first acceptor–donor–acceptor C59N-SiPc-C59N dumbbell triad 2 was accomplished. The two C59N-based materials were comprehensively characterized with the aid of NMR spectroscopy, MALDI-MS as well as DFT calculations and their redox and photophysical properties were evaluated with CV and steady-state and time-resolved absorption and photoluminescence spectroscopy measurements. Notably, femtosecond transient absorption spectroscopy assays revealed that both dyad 1 and triad 2 undergo, after selective photoexcitation of the SiPc moiety, photoinduced electron transfer from the singlet excited state of the SiPc moiety to the azafullerene counterpart to produce the charge-separated state, with lifetimes of 660 ps, in the case of dyad 1, and 810 ps, in the case of triad 2. The current results are expected to have significant implications en route to the design of advanced C59N-based donor–acceptor systems targeting energy conversion applications.",

keywords = "azafullerene, donor–acceptor systems, materials science, photoinduced electron transfer, silicon phthalocyanine",

author = "Georgios Rotas and Luis Mart{\'i}n-Gomis and Kei Ohkubo and Fernando Fern{\'a}ndez-L{\'a}zaro and Shunichi Fukuzumi and Nikos Tagmatarchis and {\'A}ngela Sastre-Santos",

note = "Funding Information: This research was financially supported by the General Secretariat for Research and Technology and European Commission, through the European Fund for Regional Development, 2007–2013 action “Development of Research Centres-ΚΡΗΠΙΣ”, project 447963 “New Multifunctional Nanostructured Materials and Devices - POLYNANO” (to N.T.), the Spanish Ministry of Economy and Competitiveness (Mineco) of Spain (CTQ2014-55798-R), Generalitat Valenciana (Prometeo 2012/010) and by JSPS KAKENHI (no. 16H02268 to S.F., nos. 16K13964, 26620154 and 26288037 to K.O.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT); SENTAN projects from JST, Japan (to S.F.). Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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Rotas, G, Martín-Gomis, L, Ohkubo, K, Fernández-Lázaro, F, Fukuzumi, S, Tagmatarchis, N & Sastre-Santos, Á 2016, 'Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation', Chemistry - A European Journal, vol. 22, no. 42, pp. 15137-15143. https://doi.org/10.1002/chem.201603065

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T1 - Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation

AU - Rotas, Georgios

AU - Martín-Gomis, Luis

AU - Ohkubo, Kei

AU - Fernández-Lázaro, Fernando

AU - Fukuzumi, Shunichi

AU - Tagmatarchis, Nikos

AU - Sastre-Santos, Ángela

N1 - Funding Information: This research was financially supported by the General Secretariat for Research and Technology and European Commission, through the European Fund for Regional Development, 2007–2013 action “Development of Research Centres-ΚΡΗΠΙΣ”, project 447963 “New Multifunctional Nanostructured Materials and Devices - POLYNANO” (to N.T.), the Spanish Ministry of Economy and Competitiveness (Mineco) of Spain (CTQ2014-55798-R), Generalitat Valenciana (Prometeo 2012/010) and by JSPS KAKENHI (no. 16H02268 to S.F., nos. 16K13964, 26620154 and 26288037 to K.O.) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT); SENTAN projects from JST, Japan (to S.F.). Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2016/10/10

Y1 - 2016/10/10

N2 - The synthesis of a donor–acceptor silicon phthalocyanine (SiPc)-azafullerene (C59N) dyad 1 and of the first acceptor–donor–acceptor C59N-SiPc-C59N dumbbell triad 2 was accomplished. The two C59N-based materials were comprehensively characterized with the aid of NMR spectroscopy, MALDI-MS as well as DFT calculations and their redox and photophysical properties were evaluated with CV and steady-state and time-resolved absorption and photoluminescence spectroscopy measurements. Notably, femtosecond transient absorption spectroscopy assays revealed that both dyad 1 and triad 2 undergo, after selective photoexcitation of the SiPc moiety, photoinduced electron transfer from the singlet excited state of the SiPc moiety to the azafullerene counterpart to produce the charge-separated state, with lifetimes of 660 ps, in the case of dyad 1, and 810 ps, in the case of triad 2. The current results are expected to have significant implications en route to the design of advanced C59N-based donor–acceptor systems targeting energy conversion applications.

AB - The synthesis of a donor–acceptor silicon phthalocyanine (SiPc)-azafullerene (C59N) dyad 1 and of the first acceptor–donor–acceptor C59N-SiPc-C59N dumbbell triad 2 was accomplished. The two C59N-based materials were comprehensively characterized with the aid of NMR spectroscopy, MALDI-MS as well as DFT calculations and their redox and photophysical properties were evaluated with CV and steady-state and time-resolved absorption and photoluminescence spectroscopy measurements. Notably, femtosecond transient absorption spectroscopy assays revealed that both dyad 1 and triad 2 undergo, after selective photoexcitation of the SiPc moiety, photoinduced electron transfer from the singlet excited state of the SiPc moiety to the azafullerene counterpart to produce the charge-separated state, with lifetimes of 660 ps, in the case of dyad 1, and 810 ps, in the case of triad 2. The current results are expected to have significant implications en route to the design of advanced C59N-based donor–acceptor systems targeting energy conversion applications.

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KW - donor–acceptor systems

KW - materials science

KW - photoinduced electron transfer

KW - silicon phthalocyanine

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U2 - 10.1002/chem.201603065

DO - 10.1002/chem.201603065

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VL - 22

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JO - Chemistry - A European Journal

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ER -

Axially Substituted Silicon Phthalocyanine as Electron Donor in a Dyad and Triad with Azafullerene as Electron Acceptor for Photoinduced Charge Separation

Abstract

Bibliographical note

Keywords

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