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Shirai Y, Guerrero JM, Sasaki T, et al. Fullerene/thiol-terminated molecules. J Org Chem. 2009;74(20):7885-97doi: 10.1021/jo901701j.
Shirai, Y., Guerrero, J. M., Sasaki, T., He, T., Ding, H., Vives, G., Yu, B. C., Cheng, L., Flatt, A. K., Taylor, P. G., Gao, Y., & Tour, J. M. (2009). Fullerene/thiol-terminated molecules. The Journal of organic chemistry, 74(20), 7885-97. https://doi.org/10.1021/jo901701j
Shirai, Yasuhiro, et al. "Fullerene/thiol-terminated molecules." The Journal of organic chemistry vol. 74,20 (2009): 7885-97. doi: https://doi.org/10.1021/jo901701j
Shirai Y, Guerrero JM, Sasaki T, He T, Ding H, Vives G, Yu BC, Cheng L, Flatt AK, Taylor PG, Gao Y, Tour JM. Fullerene/thiol-terminated molecules. J Org Chem. 2009 Oct 16;74(20):7885-97. doi: 10.1021/jo901701j. PMID: 19757798.
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J Org Chem. 2009 Oct 16;74(20):7885-97. doi: 10.1021/jo901701j.

Fullerene/thiol-terminated molecules.

The Journal of organic chemistry

Yasuhiro Shirai, Jason M Guerrero, Takashi Sasaki, Tao He, Huanjun Ding, Guillaume Vives, Byung-Chan Yu, Long Cheng, Austen K Flatt, Priscilla G Taylor, Yongli Gao, James M Tour

Affiliations

  1. Department of Chemistry, Smalley Institute for Nanoscale Science and Technology, Rice University, MS-222, 6100 Main Street, Houston, Texas 77005, USA.

PMID: 19757798 DOI: 10.1021/jo901701j

Abstract

A series of fullerene-terminated oligo(phenylene ethynylene) (OPEs) have been synthesized for potential use in electronic or optoelectronic device monolayers. Electronic properties such as the energy levels and the distribution of HOMOs and LUMOs of fullerene-terminated OPEs have been calculated using the ab initio method at the B3LYP/6-31G(d) level. The calculations have revealed the concentration of frontier orbitals on the fullerene cage and a narrow distribution of HOMO-LUMO energy gaps. Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy studies have been performed to further examine the electronic properties of the fullerene-terminated OPEs on gold surfaces. The obtained broad photoelectron spectra suggest that there are strong intermolecular interactions in the fullerene self-assembled monolayers, and the small bandgap (approximately 1.5 eV), determined by the photoelectron spectroscopy, indicates the unique nature of the fullerene-terminated OPEs in which the C(60) moiety can be connected to the Au surface through the conjugated OPE backbone.

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