Abstract
In this work we examine small conjugated molecules bearing a thiol headgroup as self assembled monolayers (SAM). Functional groups in the SAM-active molecule shift the work function of gold to n-channel semiconductor regimes and improve the wettability of the surface. We examine the effect of the presence of methylene linkers on the orientation of the molecule within the SAM. 3,4,5-Trimethoxythiophenol (TMP-SH) and 3,4,5-trimethoxybenzylthiol (TMP-CH2-SH) were first subjected to computational analysis, predicting work function shifts of -430 and -310 meV. Contact angle measurements show an increase in the wetting envelope compared to that of pristine gold. Infrared (IR) measurements show tilt angles of 22 and 63°, with the methylene-linked molecule (TMP-CH2-SH) attaining a flatter orientation. The actual work function shift as measured with photoemission spectroscopy (XPS/UPS) is even larger, -600 and -430 meV, respectively. The contact resistance between gold electrodes and poly[N,N'-bis(2-octyldodecyl)-naphthalene-1,4:5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5'-(2,2'-bithiophene) (Polyera Aktive Ink, N2200) in n-type OFETs is demonstrated to decrease by 3 orders of magnitude due to the use of TMP-SH and TMP-CH2-SH. The effectiv...Continue Reading
References
Sep 15, 1992·Physical Review. B, Condensed Matter·H L Skriver, N M Rosengaard
Apr 28, 2001·Annual Review of Physical Chemistry·D K Schwartz
Jun 20, 1996·Chemical Reviews·Abraham Ulman
Apr 25, 2002·Journal of the American Chemical Society·John OfferPhilip E Dawson
Nov 10, 2006·The Journal of Physical Chemistry. B·Paul C Rusu, Geert Brocks
May 30, 2008·Accounts of Chemical Research·Georg HeimelJean-Luc Bredas
Jan 23, 2009·Nature·He YanAntonio Facchetti
Apr 1, 2009·Journal of the American Chemical Society·Hakan UstaTobin J Marks
Apr 1, 2009·Journal of the American Chemical Society·Chang Ho SohnJ L Beauchamp
Apr 24, 2010·Advanced Materials·Georg HeimelEgbert Zojer
May 4, 2010·Advanced Materials·Yugeng Wen, Yunqi Liu
May 28, 2011·Accounts of Chemical Research·Hakan UstaTobin J Marks
Feb 23, 2012·Advanced Materials·Dario Natali, Mario Caironi
Apr 21, 2012·Science·Yinhua ZhouBernard Kippelen
Jun 6, 2012·ACS Applied Materials & Interfaces·Shu ZhongWei Chen
Jul 13, 2012·Chemical Reviews·Zhen Zhang, John T Yates
Feb 21, 2013·Nature Chemistry·G HeimelN Koch
Mar 13, 2014·Advanced Materials·Gerardo Hernandez-SosaNorman Mechau
Oct 18, 2014·ACS Applied Materials & Interfaces·Milan AltRobert Lovrincic
Citations
Jun 9, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Kunjie WuYancheng Meng
Mar 3, 2017·Macromolecular Rapid Communications·Haw-Lih SuMohammed Al-Hashimi
Aug 14, 2020·Physical Chemistry Chemical Physics : PCCP·James B DerrValentine I Vullev
Jun 21, 2018·The Journal of Physical Chemistry Letters·Frank S BenneckendorfKlaus Müllen
Dec 12, 2019·ACS Applied Materials & Interfaces·Frank S BenneckendorfKlaus Müllen