Jump to main content
Jump to site search

Issue 11, 2015
Previous Article Next Article

Tridentate benzylthiols on Au(111): control of self-assembly geometry

Author affiliations


A set of hexasubstituted benzene derivatives with three thiol groups in the 1, 3, 5 positions and varied aliphatic substituents in the 2, 4, 6 positions (Me3-BTMT, Et3-BTMT, ODe3-BTMT) has been synthesized and self-assembled on Au(111). The resulting self-assembled monolayers (SAMs) are characterized by scanning tunneling microscopy (STM), X-ray photoelectron spectroscopy (XPS), and electrochemistry. The molecular orientation and long-range order are affected by the “gear effect” of the hexasubstituted benzene ring and van der Waals interactions between the physisorbed alkyl chains drive. Me3-BTMT adopts a standing up orientation which results in the highest molecular surface density but also the lowest degree of chemisorption (1 to 2 Au–S bonds per molecule). In contrast, Et3-BTMT favors a lying down orientation with a greater number of surface-bonded thiol groups (2 to 3) per molecule, associated with the peculiar geometry of this molecule. Finally, ODe3-BTMT adsorbs mainly in a lying down orientation, forming the SAM with the highest degree of chemisorption (all thiol groups are gold-bonded) and the lowest molecular areal density.

Graphical abstract: Tridentate benzylthiols on Au(111): control of self-assembly geometry

Back to tab navigation

Supplementary files

Publication details

The article was received on 05 Dec 2014, accepted on 09 Feb 2015 and first published on 12 Feb 2015

Article type: Paper
DOI: 10.1039/C4NR07207C
Author version
Download author version (PDF)
Nanoscale, 2015,7, 5014-5022

  •   Request permissions

    Tridentate benzylthiols on Au(111): control of self-assembly geometry

    M. A. Mezour, I. I. Perepichka, O. Ivasenko, R. B. Lennox and D. F. Perepichka, Nanoscale, 2015, 7, 5014
    DOI: 10.1039/C4NR07207C

Search articles by author