Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C 60

Isla H, Grimm B, Perez EM, Rosario Torres M, Angeles Herranz M, Viruela R, Arago J, Orti E, Guldi DM, Martin N (2012)

Publication Type: Journal article, Original article

Publication year: 2012

Journal

Chemical Science Royal Society of Chemistry

Original Authors: Isla H., Grimm B., Perez E.M., Rosario Torres M., Angeles Herranz M., Viruela R., Arago J., Orti E., Guldi D.M., Martin N.

Publisher: Royal Society of Chemistry

Book Volume: 3

Pages Range: 498-508

Journal Issue: 2

DOI: 10.1039/c1sc00669j

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 C in solution with binding constants in the range of 10 -10 M 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 C , 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 1C associate the fully charge-separated state 1 C 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. © 2012 The Royal Society of Chemistry.

Authors with CRIS profile

Bruno Grimm Graduiertenzentrum der FAU Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Complutense de Madrid (UCM) ES Spain (ES) University of València / Universitat de València ES Spain (ES) IMDEA-Nanociencia ES Spain (ES)

How to cite

APA:

Isla, H., Grimm, B., Perez, E.M., Rosario Torres, M., Angeles Herranz, M., Viruela, R.,... Martin, N. (2012). Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C 60. Chemical Science, 3(2), 498-508. https://doi.org/10.1039/c1sc00669j

MLA:

Isla, Helena, et al. "Bowl-shape electron donors with absorptions in the visible range of the solar spectrum and their supramolecular assemblies with C 60." Chemical Science 3.2 (2012): 498-508.

BibTeX: Download