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

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14 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 languageEnglish
Pages (from-to)15137-15143
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number42
DOIs
StatePublished - 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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