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Issue 2, 2012
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Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C60

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Abstract

We describe the synthesis, electronic, optical and photophysical properties of a family of three electron-donor bowl-shaped organic molecules that absorb light in the whole range of the visible spectrum (up to 800 nm in one case), and associate C60 in solution with binding constants in the range of 104–102 M−1 as measured from both UV-vis and fluorescence titrations in several solvents. These molecules are π-extended derivatives of tetrathiafulvalene, based on a truxene core to which two or three units of dithiole are covalently attached. The inclusion of the bulky dithiole groups is responsible for their bowl-shape geometry, which allows them to associate with C60, and their electron-donor character. The symmetric derivative 1, with three dithiole units, absorbs light in the 370–520 nm range. Exchanging one of the dithiole groups by an electron-withdrawing group, ketone (2) and dicyanomethylene (3), results in an intramolecular push–pull effect that extends the absorption to nearly 700 nm in the case of 2, and up to 800 nm in the case of 3. Transient absorption measurements, supported by spectroelectrochemical and radiolytical experiments, reveal that upon photoexcitation of the 1∙C60 associate the fully charge-separated state 1•+∙C60 is generated, with lifetimes of hundreds of picoseconds. Molecular-level understanding of the electronic and supramolecular properties of 1–3 is provided by density functional theory calculations.

Graphical abstract: Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C60

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Publication details

The article was received on 13 Sep 2011, accepted on 17 Oct 2011 and first published on 19 Oct 2011


Article type: Edge Article
DOI: 10.1039/C1SC00669J
Chem. Sci., 2012,3, 498-508

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    Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C60

    H. Isla, B. Grimm, E. M. Pérez, M. Rosario Torres, M. Ángeles Herranz, R. Viruela, J. Aragó, E. Ortí, D. M. Guldi and N. Martín, Chem. Sci., 2012, 3, 498
    DOI: 10.1039/C1SC00669J

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