A simple vaporous probe with atomic-scale sensitivity to structural ordering and orientation of molecular assembly

Cheng, Han-Wen; Wu, Zhi-Peng; Yan, Shan; Li, Jing; Shan, Shiyao; Wang, Lichang; Porter, Marc D.; Zhong, Chuan-Jian

doi:10.1039/c9sc01656b

Title: A simple vaporous probe with atomic-scale sensitivity to structural ordering and orientation of molecular assembly

Journal Article · 19 June 2019 · Chemical Science

DOI: https://doi.org/10.1039/c9sc01656b · OSTI ID:1624977

^[1]; Wu, Zhi-Peng ^[2]; Yan, Shan ^[2]; Li, Jing ^[2]; Shan, Shiyao ^[2];

^[3];

^[4];

^[2]

Shanghai Inst. of Technology (China)
State Univ. of New York (SUNY), Binghamton, NY (United States)
Southern Illinois Univ., Carbondale, IL (United States)
Univ. of Utah, Salt Lake City, UT (United States)

Understanding the structural ordering and orientation of interfacial molecular assemblies requires an insight into the penetration depth of the probe molecules which determines the interfacial reactivity. In contrast to the conventional liquid probe-based contact angle measurement in which penetration depth is complicated by the liquid cohesive interaction, we report here a new approach that features a simple combination of vaporous hexane, which involves only van der Waals interaction, and quartz crystal microbalance operated at the third harmonic resonance, which is sensitive to sub-monolayer (0.2%) adsorption. Using this combination, we demonstrated the ability of probing the structural ordering and orientation of the self-assembled monolayers with a sensitivity from penetrating the top portion of the monolayers to interacting with the very top atomic structure at the interface. The determination of the dependence of the adsorption energy of vaporous hexane on the penetration depth in the molecular assembly allowed us to further reveal the atomic-scale origin of the odd–even oscillation, which is also substantiated by density functional theory calculations. The findings have broader implications for designing interfacial reactivities of molecular assemblies with atomic-scale depth precision.

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Research Organization:: Ames Laboratory (AMES), Ames, IA (United States)

Sponsoring Organization:: USDOE; National Science Foundation (NSF); National Institutes of Health (NIH); Utah Science Technology and Research (USTAR); NNSFC

Grant/Contract Number:: AC02-07CH11358; CHE 1566283; IIP 1640669; U01CA151650; 31800830

OSTI ID:: 1624977

Journal Information:: Chemical Science, Vol. 10, Issue 29; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 6 works

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References (54)

Molecular-Scale Electronics: From Concept to Function Xiang, Dong; Wang, Xiaolong; Jia, Chuancheng Chemical Reviews, Vol. 116, Issue 7 https://doi.org/10.1021/acs.chemrev.5b00680	journal	March 2016
Odd–Even Effects on the Structure, Stability, and Phase Transition of Alkanethiol Self-Assembled Monolayers Ramin, Leyla; Jabbarzadeh, Ahmad Langmuir, Vol. 27, Issue 16 https://doi.org/10.1021/la201467b	journal	August 2011
The Origin of the Odd–Even Effect in the Tunneling Rates across EGaIn Junctions with Self-Assembled Monolayers (SAMs) of n -Alkanethiolates Jiang, Li; Sangeeth, C. S. Suchand; Nijhuis, Christian A. Journal of the American Chemical Society, Vol. 137, Issue 33 https://doi.org/10.1021/jacs.5b05761	journal	August 2015
Even the Odd Numbers Help: Failure Modes of SAM-Based Tunnel Junctions Probed via Odd-Even Effects Revealed in Synchrotrons and Supercomputers Thompson, Damien; Nijhuis, Christian A. Accounts of Chemical Research, Vol. 49, Issue 10 https://doi.org/10.1021/acs.accounts.6b00256	journal	September 2016
Supramolecular vs Electronic Structure: The Effect of the Tilt Angle of the Active Group in the Performance of a Molecular Diode Song, Peng; Yuan, Li; Roemer, Max Journal of the American Chemical Society, Vol. 138, Issue 18 https://doi.org/10.1021/jacs.6b02208	journal	April 2016
Odd–Even Effects in Electroactive Self-Assembled Monolayers Investigated by Electrochemical Surface Plasmon Resonance and Impedance Spectroscopy Feng, Yanqi; Dionne, Eric R.; Toader, Violeta The Journal of Physical Chemistry C, Vol. 121, Issue 44 https://doi.org/10.1021/acs.jpcc.7b08053	journal	October 2017
Anomalously Rapid Tunneling: Charge Transport across Self-Assembled Monolayers of Oligo(ethylene glycol) Baghbanzadeh, Mostafa; Bowers, Carleen M.; Rappoport, Dmitrij Journal of the American Chemical Society, Vol. 139, Issue 22 https://doi.org/10.1021/jacs.7b02770	journal	May 2017
Understanding Odd−Even Effects in Organic Self-Assembled Monolayers Tao, Feng; Bernasek, Steven L. Chemical Reviews, Vol. 107, Issue 5 https://doi.org/10.1021/cr050258d	journal	May 2007
Supramolecular Structure of the Monolayer Triggers Odd–Even Effects in the Tunneling Rates across Noncovalent Junctions on Graphene Song, Peng; Thompson, Damien; Annadata, Harshini V. The Journal of Physical Chemistry C, Vol. 121, Issue 8 https://doi.org/10.1021/acs.jpcc.6b12949	journal	February 2017
Graphite Microparticles as Coatings for Quartz Crystal Microbalance-Based Gas Sensors Shinar, Ruth; Liu, Guojun; Porter, Marc D. Analytical Chemistry, Vol. 72, Issue 24 https://doi.org/10.1021/ac0009548	journal	December 2000
Vapor-Phase Adsorption of Hexane and Benzene on Activated Carbon Fabric Cloth: Equilibria and Rate Studies ^† Singh, Kunwar P.; Mohan, Dinesh; Tandon, G. S. Industrial & Engineering Chemistry Research, Vol. 41, Issue 10 https://doi.org/10.1021/ie0105674	journal	May 2002
Functional Molecular Junctions Derived from Double Self-Assembled Monolayers Seo, Sohyeon; Hwang, Eunhee; Cho, Yunhee Angewandte Chemie International Edition, Vol. 56, Issue 40 https://doi.org/10.1002/anie.201705518	journal	August 2017
Odd−Even Variations in the Wettability of n- Alkanethiolate Monolayers on Gold by Water and Hexadecane: A Molecular Dynamics Simulation Study Srivastava, Piyush; Chapman, Walter G.; Laibinis, Paul E. Langmuir, Vol. 21, Issue 26 https://doi.org/10.1021/la051535e	journal	December 2005
Combined Nitrogen, Hexane, and Benzene Adsorption Characterization of Pores and Surfaces of Lyophobic Mesoporous Silicas Roshchina, T. M.; Shonija, N. K.; Bernardoni, F. Langmuir, Vol. 30, Issue 31 https://doi.org/10.1021/la500660s	journal	July 2014
Bending Potential as an Important Factor for the Structure of Monomolecular Thiolate Layers on GaAs Substrates Lu, Hao; Terfort, Andreas; Zharnikov, Michael The Journal of Physical Chemistry Letters, Vol. 4, Issue 13 https://doi.org/10.1021/jz401091y	journal	June 2013
The role of van der Waals forces in the performance of molecular diodes Nerngchamnong, Nisachol; Yuan, Li; Qi, Dong-Chen Nature Nanotechnology, Vol. 8, Issue 2 https://doi.org/10.1038/nnano.2012.238	journal	January 2013
Nanoscale Lacing by Electrons Cheng, Han-Wen; Wang, Jie; Li, Yong-Jun Small, Vol. 14, Issue 20 https://doi.org/10.1002/smll.201800598	journal	April 2018
Structure and interfacial properties of spontaneously adsorbed n-alkanethiolate monolayers on evaporated silver surfaces Walczak, Mary M.; Chung, Chinkap; Stole, Scott M. Journal of the American Chemical Society, Vol. 113, Issue 7 https://doi.org/10.1021/ja00007a004	journal	March 1991
Transition from direct to inverted charge transport Marcus regions in molecular junctions via molecular orbital gating Yuan, Li; Wang, Lejia; Garrigues, Alvar R. Nature Nanotechnology, Vol. 13, Issue 4 https://doi.org/10.1038/s41565-018-0068-4	journal	March 2018
Characterization of a quartz crystal microbalance with simultaneous mass and liquid loading Martin, Stephen J.; Granstaff, Victoria Edwards.; Frye, Gregory C. Analytical Chemistry, Vol. 63, Issue 20 https://doi.org/10.1021/ac00020a015	journal	October 1991
Tuning Thiol‐Based Self‐Assembled Monolayer Chemistry on a Gold Surface towards the Synthesis of Biochemical Fuel Li, Guangle; Fei, Jinbo; Xu, Youqian Angewandte Chemie International Edition, Vol. 58, Issue 4 https://doi.org/10.1002/anie.201812552	journal	January 2019
Odd–Even Effect in Molecular Packing of Self-Assembled Monolayers of Biphenyl-Substituted Fatty Acid on Ag(111) Krzykawska, Anna; Szwed, Monika; Ossowski, Jakub The Journal of Physical Chemistry C, Vol. 122, Issue 1 https://doi.org/10.1021/acs.jpcc.7b10806	journal	December 2017
Elucidating the Role of Molecule–Electrode Interfacial Defects in Charge Tunneling Characteristics of Large-Area Junctions Kong, Gyu Don; Jin, Junji; Thuo, Martin Journal of the American Chemical Society, Vol. 140, Issue 38 https://doi.org/10.1021/jacs.8b08146	journal	September 2018
Odd–Even Effects in the Structure and Stability of Azobenzene-Substituted Alkanethiolates on Au(111) and Ag(111) Substrates Gnatek, Dominika; Schuster, Swen; Ossowski, Jakub The Journal of Physical Chemistry C, Vol. 119, Issue 46 https://doi.org/10.1021/acs.jpcc.5b07899	journal	November 2015
Self-assembled monolayers in organic electronics Casalini, Stefano; Bortolotti, Carlo Augusto; Leonardi, Francesca Chemical Society Reviews, Vol. 46, Issue 1 https://doi.org/10.1039/C6CS00509H	journal	January 2017
Mapping Orientation Differences of Terminal Functional Groups by Friction Force Microscopy Wong, Sze-Shun; Takano, Hajime; Porter, Marc D. Analytical Chemistry, Vol. 70, Issue 24 https://doi.org/10.1021/ac9807870	journal	December 1998
Odd–Even Effect in the Hydrophobicity of n -Alkanethiolate Self-Assembled Monolayers Depends upon the Roughness of the Substrate and the Orientation of the Terminal Moiety Newcomb, Lucas B.; Tevis, Ian D.; Atkinson, Manza B. J. Langmuir, Vol. 30, Issue 40 https://doi.org/10.1021/la5032569	journal	September 2014
Quantifying Gauche Defects and Phase Evolution in Self-Assembled Monolayers through Sessile Drops Chen, Jiahao; Chang, Boyce; Oyola-Reynoso, Stephanie ACS Omega, Vol. 2, Issue 5 https://doi.org/10.1021/acsomega.7b00355	journal	May 2017
Dual-harmonic oscillator for quartz crystal resonator sensors Ferrari, M.; Ferrari, V.; Kanazawa, K. K. Sensors and Actuators A: Physical, Vol. 145-146 https://doi.org/10.1016/j.sna.2007.10.087	journal	July 2008
Empirical Evidence for Roughness-Dependent Limit in Observation of Odd–Even Effect in Wetting Properties of Polar Liquids on n -Alkanethiolate Self-Assembled Monolayers Wang, Zhengjia; Chen, Jiahao; Oyola-Reynoso, Stephanie Langmuir, Vol. 32, Issue 32 https://doi.org/10.1021/acs.langmuir.6b02159	journal	August 2016
Competition of van der Waals and chemical forces on gold–sulfur surfaces and nanoparticles Reimers, Jeffrey R.; Ford, Michael J.; Marcuccio, Sebastian M. Nature Reviews Chemistry, Vol. 1, Issue 2 https://doi.org/10.1038/s41570-017-0017	journal	February 2017
Chain-length-dependent change in the structure of self-assembled monolayers of n -alkanethiols on Au(111) probed by broad-bandwidth sum frequency generation spectroscopy Nishi, Naoya; Hobara, Daisuke; Yamamoto, Masahiro The Journal of Chemical Physics, Vol. 118, Issue 4 https://doi.org/10.1063/1.1531098	journal	January 2003
Gradients of Rectification: Tuning Molecular Electronic Devices by the Controlled Use of Different-Sized Diluents in Heterogeneous Self-Assembled Monolayers Kong, Gyu Don; Kim, Miso; Cho, Soo Jin Angewandte Chemie International Edition, Vol. 55, Issue 35 https://doi.org/10.1002/anie.201604748	journal	July 2016
The crystalline structures of the even alkanes hexane, octane, decane, dodecane and tetradecane monolayers adsorbed on graphite at submonolayer coverages and from the liquidElectronic Supplementary Information available. See http://www.rsc.org/suppdata/cp/b1/b108190j/ Arnold, Thomas; Thomas, Robert K.; Castro, Miguel A. Physical Chemistry Chemical Physics, Vol. 4, Issue 2 https://doi.org/10.1039/b108190j	journal	January 2002
Assessing the Role of Capping Molecules in Controlling Aggregative Growth of Gold Nanoparticles in Heated Solution Cheng, Han-Wen; Schadt, Mark J.; Zhong, Chuan-Jian Chemistry - An Asian Journal, Vol. 11, Issue 1 https://doi.org/10.1002/asia.201500857	journal	October 2015
Balance of Structure−Building Forces in Selenium-Based Self-Assembled Monolayers Shaporenko, Andrey; Müller, Jan; Weidner, Tobias Journal of the American Chemical Society, Vol. 129, Issue 8 https://doi.org/10.1021/ja068916e	journal	February 2007
Odd–Even Effects in Charge Transport across n -Alkanethiolate-Based SAMs Baghbanzadeh, Mostafa; Simeone, Felice C.; Bowers, Carleen M. Journal of the American Chemical Society, Vol. 136, Issue 48 https://doi.org/10.1021/ja509436k	journal	November 2014
Electrochemical and X-ray photoelectron spectroscopic evidence for differences in the binding sites of alkanethiolate monolayers chemisorbed at gold Walczak, Mary M.; Alves, Carla A.; Lamp, Brian D. Journal of Electroanalytical Chemistry, Vol. 396, Issue 1-2 https://doi.org/10.1016/0022-0728(95)04056-T	journal	October 1995
Gradients of Rectification: Tuning Molecular Electronic Devices by the Controlled Use of Different-Sized Diluents in Heterogeneous Self-Assembled Monolayers Kong, Gyu Don; Kim, Miso; Cho, Soo Jin Angewandte Chemie, Vol. 128, Issue 35 https://doi.org/10.1002/ange.201604748	journal	July 2016
Functional Molecular Junctions Derived from Double Self-Assembled Monolayers Seo, Sohyeon; Hwang, Eunhee; Cho, Yunhee Angewandte Chemie, Vol. 129, Issue 40 https://doi.org/10.1002/ange.201705518	journal	August 2017
Dual-Harmonic Oscillator for Quartz Crystal Resonator Sensors Ferrari, M.; Ferrari, V.; Kanazawa, K. K. TRANSDUCERS 2007 - 2007 International Solid-State Sensors, Actuators and Microsystems Conference https://doi.org/10.1109/sensor.2007.4300114	conference	June 2007
Tuning Thiol‐Based Self‐Assembled Monolayer Chemistry on a Gold Surface towards the Synthesis of Biochemical Fuel Li, Guangle; Fei, Jinbo; Xu, Youqian Angewandte Chemie, Vol. 131, Issue 4 https://doi.org/10.1002/ange.201812552	journal	December 2018
Understanding Odd—Even Effects in Organic Self-Assembled Monolayers Tao, Feng; Bernasek, Steven L. ChemInform, Vol. 38, Issue 31 https://doi.org/10.1002/chin.200731275	journal	July 2007
Even the Odd Numbers Help: Failure Modes of SAM-Based Tunnel Junctions Probed via Odd-Even Effects Revealed in Synchrotrons and Supercomputers Thompson, Damien; Nijhuis, Christian A. Accounts of Chemical Research, Vol. 49, Issue 10 https://doi.org/10.1021/acs.accounts.6b00256	journal	September 2016
Molecular-Scale Electronics: From Concept to Function Xiang, Dong; Wang, Xiaolong; Jia, Chuancheng Chemical Reviews, Vol. 116, Issue 7 https://doi.org/10.1021/acs.chemrev.5b00680	journal	March 2016
Empirical Evidence for Roughness-Dependent Limit in Observation of Odd–Even Effect in Wetting Properties of Polar Liquids on n -Alkanethiolate Self-Assembled Monolayers Wang, Zhengjia; Chen, Jiahao; Oyola-Reynoso, Stephanie Langmuir, Vol. 32, Issue 32 https://doi.org/10.1021/acs.langmuir.6b02159	journal	August 2016
Understanding Odd−Even Effects in Organic Self-Assembled Monolayers Tao, Feng; Bernasek, Steven L. Chemical Reviews, Vol. 107, Issue 5 https://doi.org/10.1021/cr050258d	journal	May 2007
Balance of Structure−Building Forces in Selenium-Based Self-Assembled Monolayers Shaporenko, Andrey; Müller, Jan; Weidner, Tobias Journal of the American Chemical Society, Vol. 129, Issue 8 https://doi.org/10.1021/ja068916e	journal	February 2007
Odd–Even Effects in Charge Transport across n -Alkanethiolate-Based SAMs Baghbanzadeh, Mostafa; Simeone, Felice C.; Bowers, Carleen M. Journal of the American Chemical Society, Vol. 136, Issue 48 https://doi.org/10.1021/ja509436k	journal	November 2014
Supramolecular vs Electronic Structure: The Effect of the Tilt Angle of the Active Group in the Performance of a Molecular Diode Song, Peng; Yuan, Li; Roemer, Max Journal of the American Chemical Society, Vol. 138, Issue 18 https://doi.org/10.1021/jacs.6b02208	journal	April 2016
Odd–Even Effects on the Structure, Stability, and Phase Transition of Alkanethiol Self-Assembled Monolayers Ramin, Leyla; Jabbarzadeh, Ahmad Langmuir, Vol. 27, Issue 16 https://doi.org/10.1021/la201467b	journal	August 2011
Charge transport in the inverted Marcus region Hihath, Joshua Nature Nanotechnology, Vol. 13, Issue 4 https://doi.org/10.1038/s41565-018-0115-1	journal	March 2018
Chemiresistive properties regulated by nanoscale curvature in molecularly-linked nanoparticle composite assembly Cheng, Han-Wen; Yan, Shan; Han, Li Nanoscale, Vol. 9, Issue 11 https://doi.org/10.1039/c6nr09315a	journal	January 2017
Odd–even effect in two dimensions induced by the bicomponent blends of isobutenyl compounds Kikkawa, Yoshihiro; Tsuzuki, Seiji; Taguchi, Kazuhiro Physical Chemistry Chemical Physics, Vol. 19, Issue 21 https://doi.org/10.1039/c7cp02064c	journal	January 2017