Characterization of self-assembled monolayers of porphyrins bearing multiple thiol-derivatized rigid-rod tethers

Journal of the American Chemical Society
Amir A YasseriDavid F Bocian

Abstract

A series of multithiol-functionalized zinc porphyrins has been prepared and characterized as self-assembled monolayers (SAMs) on Au. The molecules, designated ZnPS(n) (n = 1-4), contain from one to four [(S-acetylthio)methyl]phenylethynylphenyl groups appended to the meso-position of the porphyrin; the other meso-substituents are phenyl groups. For the dithiol-functionalized molecules, both the cis- and the trans-appended structures were examined. The ZnPS(n) SAMs were investigated using X-ray photoelectron spectroscopy, Fourier transform infrared spectroscopy, and various electrochemical methods. The studies reveal the following characteristics of the ZnPS(n) SAMs. (1) The ZnPS(n) molecules bind to the Au surface via a single thiol regardless of the number of thiol appendages that are available per molecular unit. (2) The porphyrins in the ZnPS(3) and ZnPS(4) SAMs bind to the surface in a more upright orientation than the porphyrins in the ZnPS(1), cis-ZnPS(2), and trans-ZnPS(2) SAMs. The porphyrins in the ZnPS(3) and ZnPS(4) SAMs are also more densely packed than those in the cis-ZnPS(2) and trans-ZnPS(2) SAMs. The packing density of the ZnPS(3) and ZnPS(4) SAMs is similar to that of the ZnPS(1) SAMs, despite the larger size ...Continue Reading

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Citations

Jun 2, 2011·Accounts of Chemical Research·Jonathan S Lindsey, David F Bocian
Dec 19, 2009·Journal of the American Chemical Society·Michael S MillerTricia Breen Carmichael
Mar 22, 2006·Chemical Communications : Chem Comm·Chen-Fu LoChing-Yao Lin
Feb 20, 2015·Nanoscale·Mohamed A MezourDmitrii F Perepichka
Nov 21, 2007·Angewandte Chemie·Masayuki KaneharaToshiharu Teranishi
Apr 2, 2008·Nanotechnology·Qingmin XuAlex K-Y Jen
Mar 4, 2009·Chemical Reviews·Charles Michael DrainIvana Radivojevic
Sep 26, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Bostjan GenorioJames M Tour
Oct 1, 2008·Langmuir : the ACS Journal of Surfaces and Colloids·Jieying JiaoDavid F Bocian
Oct 21, 2009·The Journal of Physical Chemistry. B·Hong ZongBrian M Hoffman
Sep 23, 2009·ACS Nano·Xian Ning XieAndrew Thye Shen Wee
Nov 16, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·Solomon SsenyangeRichard L McCreery
Sep 7, 2005·Langmuir : the ACS Journal of Surfaces and Colloids·Dmitrii F PerepichkaMartin R Bryce

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