Self-assembly and chemical modifications of bisphenol a on Cu(111): interplay between ordering and thermally activated stepwise deprotonation

ACS Nano
Sybille FischerJ V Barth

Abstract

Bisphenol A (BPA) is a chemical widely used in the synthesis pathway of polycarbonates for the production of many daily used products. Besides other adverse health effects, medical studies have shown that BPA can cause DNA hypomethylation and therefore alters the epigenetic code. In the present work, the reactivity and self-assembly of the molecule was investigated under ultra-high-vacuum conditions on a Cu(111) surface. We show that the surface-confined molecule goes through a series of thermally activated chemical transitions. Scanning tunneling microscopy investigations showed multiple distinct molecular arrangements dependent on the temperature treatment and the formation of polymer-like molecular strings for temperatures above 470 K. X-ray photoelectron spectroscopy measurements revealed the stepwise deprotonation of the hydroxy groups, which allows the molecules to interact strongly with the underlying substrate as well as their neighboring molecules and therefore drive the organization into distinct structural arrangements. On the basis of the combined experimental evidence in conjunction with density functional theory calculations, structural models for the self-assemblies after the thermal treatment were elaborated.

References

Jul 15, 1996·Physical Review. B, Condensed Matter·S GoedeckerJ Hutter
Nov 17, 2001·Biomacromolecules·F H SilverW J Landis
Feb 28, 2002·Biomacromolecules·Hiroshi UyamaShiro Kobayashi
Jul 18, 2002·The Journal of Biological Chemistry·Lin Jiang, Luhua Lai
Aug 28, 2003·Journal of the American Chemical Society·Hannes SpillmannKlaus Kern
Jan 29, 2005·Angewandte Chemie·Nian LinKlaus Kern
Jul 23, 2005·Angewandte Chemie·Marie-Christine BlümWolf-Dieter Schneider
Sep 7, 2006·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Alexandre DmitrievKlaus Kern
Dec 13, 2006·Langmuir : the ACS Journal of Surfaces and Colloids·Albano CossaroMaurizio Canepa
Feb 10, 2007·Chemistry : a European Journal·Dietmar PayerKlaus Kern
May 17, 2007·The Review of Scientific Instruments·I HorcasA M Baro
Aug 3, 2007·Proceedings of the National Academy of Sciences of the United States of America·Dana C DolinoyRandy L Jirtle
Sep 25, 2007·The Journal of Chemical Physics·Joost VandeVondele, Jürg Hutter
Feb 26, 2010·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Jason G BromerHugh S Taylor
Sep 4, 2010·ACS Nano·Erin V IskiE Charles H Sykes
May 9, 2012·Proceedings of the National Academy of Sciences of the United States of America·Andrew P TharpAna M Soto
Oct 24, 2012·Physical Chemistry Chemical Physics : PCCP·Emmanuel ArrasJohannes V Barth
Jun 7, 2012·The Journal of Physical Chemistry Letters·Federico GrilloJaume Veciana

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Citations

Nov 10, 2014·The Journal of Chemical Physics·K L Svane, B Hammer
Feb 9, 2016·Journal of the American Chemical Society·Qing LiLifeng Chi
Jun 25, 2014·Journal of the American Chemical Society·Aneliia ShchyrbaLutz H Gade
Jul 6, 2017·Nano Letters·Tianlong LiJoseph Wang
Jun 7, 2018·Chemical Communications : Chem Comm·Zhijie TaoJunfa Zhu
Jan 1, 2016·Nanomaterials·Thatchaphong Phatthanakittiphong, Gyu Tae Seo
Oct 20, 2018·Chemical Communications : Chem Comm·Seung Cheol OhJohannes V Barth
Jun 25, 2021·Chemical Science·Ana Cristina Gómez-HerreroJohann Coraux
Feb 12, 2017·Journal of the American Chemical Society·Huihui KongHarald Fuchs
Sep 10, 2019·ACS Nano·Lin FengJunfa Zhu
Mar 16, 2018·Journal of the American Chemical Society·Qing LiLifeng Chi
Nov 27, 2018·Journal of the American Chemical Society·Biao YangLifeng Chi

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