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Title: Enantiomer surface chemistry: conglomerate versus racemate formation on surfaces

Abstract

A comprehensive review classifying chirality expressed on surfaces and, by surveying available literature, determining the tendency for conglomeratevs.racemate formation on surfaces.

Authors:
 [1]; ORCiD logo [2]
  1. Department of Chemical Engineering; Carnegie Mellon University; Pittsburgh; USA
  2. Department of Chemical Engineering; Carnegie Mellon University; Pittsburgh; USA; W. E. Scott Institute for Energy Innovation
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
1539897
DOE Contract Number:  
SC0008703
Resource Type:
Journal Article
Journal Name:
Chemical Society Reviews
Additional Journal Information:
Journal Volume: 46; Journal Issue: 24; Journal ID: ISSN 0306-0012
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
Chemistry

Citation Formats

Dutta, Soham, and Gellman, Andrew J. Enantiomer surface chemistry: conglomerate versus racemate formation on surfaces. United States: N. p., 2017. Web. doi:10.1039/c7cs00555e.
Dutta, Soham, & Gellman, Andrew J. Enantiomer surface chemistry: conglomerate versus racemate formation on surfaces. United States. doi:10.1039/c7cs00555e.
Dutta, Soham, and Gellman, Andrew J. Sun . "Enantiomer surface chemistry: conglomerate versus racemate formation on surfaces". United States. doi:10.1039/c7cs00555e.
@article{osti_1539897,
title = {Enantiomer surface chemistry: conglomerate versus racemate formation on surfaces},
author = {Dutta, Soham and Gellman, Andrew J.},
abstractNote = {A comprehensive review classifying chirality expressed on surfaces and, by surveying available literature, determining the tendency for conglomeratevs.racemate formation on surfaces.},
doi = {10.1039/c7cs00555e},
journal = {Chemical Society Reviews},
issn = {0306-0012},
number = 24,
volume = 46,
place = {United States},
year = {2017},
month = {1}
}

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Complete Experimental Structure Determination of the p(3 × 2) pg Phase of Glycine on Cu{110}
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  • Zheleva, Zhasmina V.; Eralp, Tugce; Held, Georg
  • The Journal of Physical Chemistry C, Vol. 116, Issue 1
  • DOI: 10.1021/jp2057282

Self-Assembled Structures of Glycine on Cu(111)
journal, February 2003

  • Zhao, Xueying; Yan, Hao; Zhao, R. G.
  • Langmuir, Vol. 19, Issue 3
  • DOI: 10.1021/la0267037

Can glycine form homochiral structural domains on low-index copper surfaces?
journal, January 2003


Real Space Observation of a Chiral Phase Transition in a Two-Dimensional Organic Layer
journal, February 2000


Separation of a Racemic Mixture of Two-Dimensional Molecular Clusters by Scanning Tunneling Microscopy
journal, March 1999


Highly Enantioselective Adsorption of Small Prochiral Molecules on a Chiral Intermetallic Compound
journal, February 2015

  • Prinz, Jan; Gröning, Oliver; Brune, Harald
  • Angewandte Chemie International Edition, Vol. 54, Issue 13
  • DOI: 10.1002/anie.201410107

Direct Observation of Enantiospecific Substitution in a Two-Dimensional Chiral Phase Transition
journal, August 2010

  • Yang, Bing; Wang, Yeliang; Cun, Huanyao
  • Journal of the American Chemical Society, Vol. 132, Issue 30
  • DOI: 10.1021/ja102989y

Achieving chiral resolution in self-assembled supramolecular structures through kinetic pathways
journal, May 2011


Prochiral Guanine Adsorption on Au(111): An Entropy-Stabilized Intermixed Guanine-Quartet Chiral Structure
journal, September 2009


Coexistence of Homochiral and Heterochiral Adenine Domains at the Liquid/Solid Interface
journal, October 2007

  • Mamdouh, Wael; Dong, Mingdong; Kelly, Ross E. A.
  • The Journal of Physical Chemistry B, Vol. 111, Issue 42
  • DOI: 10.1021/jp076623h

Conglomerate with periodic enantiomer inclusion: A mechanism for homochirality erosion
journal, January 2011

  • Ahn, Seokhoon; Henssler, John T.; Matzger, Adam J.
  • Chemical Communications, Vol. 47, Issue 41
  • DOI: 10.1039/c1cc12317c

Odd/Even Effect in Self-Assembly of Chiral Molecules at the Liquid−Solid Interface:  An STM Investigation of Coadsorbate Control of Self-Assembly
journal, May 2002

  • Yablon, Dalia G.; Wintgens, David; Flynn, George W.
  • The Journal of Physical Chemistry B, Vol. 106, Issue 21
  • DOI: 10.1021/jp020152b

Structure and structural transition of chiral domains in oligo(p-phenylenevinylene) assembly investigated by scanning tunneling microscopy
journal, February 2010

  • Chen, Q.; Chen, T.; Wang, D.
  • Proceedings of the National Academy of Sciences, Vol. 107, Issue 7
  • DOI: 10.1073/pnas.1000120107

Two-dimensional OPV4 self-assembly and its coadsorption with alkyl bromide: from helix to lamellar
journal, January 2009

  • Chen, Qing; Chen, Ting; Zhang, Xu
  • Chemical Communications, Issue 25
  • DOI: 10.1039/b905281j

Direct observation of chiral oligo(p-phenylenevinylene)s with scanning tunneling microscopy
journal, January 2003

  • Gesquière, A.; Jonkheijm, P.; Schenning, A. P. H. J.
  • J. Mater. Chem., Vol. 13, Issue 9
  • DOI: 10.1039/B304517J

Crankshafts: Using Simple, Flat C 2 h -Symmetric Molecules to Direct the Assembly of Chiral 2D Nanopatterns
journal, November 2012


Spontaneous Chiral Resolution in Supramolecular Assembly of 2,4,6-Tris(2-pyridyl)-1,3,5-triazine on Au(111)
journal, April 2009

  • Zhang, Jing; Li, Bin; Cui, Xuefeng
  • Journal of the American Chemical Society, Vol. 131, Issue 16
  • DOI: 10.1021/ja9001986

Adenine monolayers on the Au(111) surface: Structure identification by scanning tunneling microscopy experiment and ab initio calculations
journal, January 2009

  • Lukas, Maya; Kelly, Ross E. A.; Kantorovich, Lev N.
  • The Journal of Chemical Physics, Vol. 130, Issue 2
  • DOI: 10.1063/1.3046690

Guanine Quartet Networks Stabilized by Cooperative Hydrogen Bonds
journal, March 2005

  • Otero, Roberto; Schöck, Maya; Molina, Luis M.
  • Angewandte Chemie International Edition, Vol. 44, Issue 15
  • DOI: 10.1002/anie.200461586

Naphtho[2,3- a ]pyrene Forms Chiral Domains on Au(111)
journal, October 2003

  • France, C. Brian; Parkinson, B. A.
  • Journal of the American Chemical Society, Vol. 125, Issue 42
  • DOI: 10.1021/ja037056o

Asymmetry Induction by Cooperative Intermolecular Hydrogen Bonds in Surface-Anchored Layers of Achiral Molecules
journal, October 2006

  • Dmitriev, Alexandre; Spillmann, Hannes; Stepanow, Sebastian
  • ChemPhysChem, Vol. 7, Issue 10
  • DOI: 10.1002/cphc.200600110

Programming Supramolecular Assembly and Chirality in Two-Dimensional Dicarboxylate Networks on a Cu(100) Surface
journal, May 2005

  • Stepanow, Sebastian; Lin, Nian; Vidal, Franck
  • Nano Letters, Vol. 5, Issue 5
  • DOI: 10.1021/nl050362a

Coexistence of Racemic and Homochiral Two-Dimensional Lattices Formed by a Prochiral Molecule: Dicarboxystilbene on Cu(110)
journal, December 2008

  • Cortés, Rocío; Mascaraque, Arantzazu; Schmidt-Weber, Philipp
  • Nano Letters, Vol. 8, Issue 12
  • DOI: 10.1021/nl801592c

Self-Assembly of Adenine on Cu(110) Surfaces
journal, April 2002

  • Chen, Qiao; Frankel, Daniel J.; Richardson, Neville V.
  • Langmuir, Vol. 18, Issue 8
  • DOI: 10.1021/la011722m

The adsorption with chiral structure of fluorene-1-carboxylic acid molecules on Cu(110) surface
journal, February 2008


Homochiral Recognition among Organic Molecules on Copper(110)
journal, March 2010

  • Cun, Huanyao; Wang, Yeliang; Yang, Bing
  • Langmuir, Vol. 26, Issue 5
  • DOI: 10.1021/la903193a

Low-Temperature Mobility and Structure Formation of a Prochiral Aromatic Thiol (2,5-Dichlorothiophenol) on Cu(111)
journal, May 2004

  • Rao, B. V.; Kwon, K. -Y.; Zhang, J.
  • Langmuir, Vol. 20, Issue 11
  • DOI: 10.1021/la030364f

Scanning tunneling microscopy/spectroscopy on self-assembly of a glycine/Cu(111) nanocavity array
journal, January 2011

  • Kanazawa, Ken; Taninaka, Atsushi; Huang, Hui
  • Chemical Communications, Vol. 47, Issue 40
  • DOI: 10.1039/c1cc11829c

Self-assembly of enantiopure domains: The case of indigo on Cu(111)
journal, February 2010

  • Villagomez, C. J.; Guillermet, O.; Goudeau, S.
  • The Journal of Chemical Physics, Vol. 132, Issue 7
  • DOI: 10.1063/1.3314725

Spontaneous Transmission of Chirality through Multiple Length Scales
journal, May 2011

  • Iski, Erin V.; Tierney, Heather L.; Jewell, April D.
  • Chemistry – A European Journal, Vol. 17, Issue 26
  • DOI: 10.1002/chem.201100268

Chiral Attachment of Styrene Mediated by Surface Dimers on Ge(100)
journal, April 2005

  • Hwang, Yun Jeong; Kim, Ansoon; Hwang, Eunkyung
  • Journal of the American Chemical Society, Vol. 127, Issue 14
  • DOI: 10.1021/ja050234o

Octyl-Decorated Fréchet-Type Dendrons: A General Motif for Visualisation of Static and Dynamic Behaviour Using Scanning Tunnelling Microscopy?
journal, February 2005

  • Merz, Leo; Güntherodt, H. -J.; Scherer, Lukas J.
  • Chemistry - A European Journal, Vol. 11, Issue 8
  • DOI: 10.1002/chem.200400984

Formation and Structure of Self-Assembled Monolayers
journal, January 1996

  • Ulman, Abraham
  • Chemical Reviews, Vol. 96, Issue 4, p. 1533-1554
  • DOI: 10.1021/cr9502357

Functional Materials Based on Self-Assembly of Polymeric Supramolecules
journal, March 2002


Adsorption and scanning-tunneling-microscope imaging of benzene on graphite and MoS 2
journal, May 1993


Absolute configuration and chiral self-assembly of rubrene on Bi(111)
journal, January 2015

  • Sun, Kai; Lan, Meng; Wang, Jun-Zhong
  • Physical Chemistry Chemical Physics, Vol. 17, Issue 39
  • DOI: 10.1039/C5CP04608D

Conformational degree and molecular orientation in rubrene film by in situ x-ray absorption spectroscopy
journal, September 2007

  • Wang, Li; Chen, Shi; Liu, Lei
  • Journal of Applied Physics, Vol. 102, Issue 6
  • DOI: 10.1063/1.2778636

Conformation-induced self-assembly of rubrene on Au(111) surface
journal, August 2009

  • Wang, Li; Kong, Huihui; Chen, Xiu
  • Applied Physics Letters, Vol. 95, Issue 9
  • DOI: 10.1063/1.3213563

Coverage-Dependent Self-Assembly of Rubrene Molecules on Noble Metal Surfaces Observed by Scanning Tunneling Microscopy
journal, May 2010

  • Pivetta, Marina; Blüm , Marie-Christine; Patthey, François
  • ChemPhysChem, Vol. 11, Issue 7
  • DOI: 10.1002/cphc.200900846

Self-assembly of Rubrene on Copper Surfaces
journal, June 2008

  • Miwa, Jill A.; Cicoira, Fabio; Bedwani, Stéphane
  • The Journal of Physical Chemistry C, Vol. 112, Issue 27
  • DOI: 10.1021/jp802762q

Self-assembly of rubrene on Cu(111)
journal, September 2008


Three-Dimensional Chirality Transfer in Rubrene Multilayer Islands on Au(111)
journal, April 2009

  • Pivetta, Marina; Blüm, Marie-Christine; Patthey, François
  • The Journal of Physical Chemistry B, Vol. 113, Issue 14
  • DOI: 10.1021/jp8104024

Conservation of Chirality in a Hierarchical Supramolecular Self-Assembled Structure with Pentagonal Symmetry
journal, August 2005

  • Blüm, Marie-Christine; Ćavar, Elizabeta; Pivetta, Marina
  • Angewandte Chemie International Edition, Vol. 44, Issue 33
  • DOI: 10.1002/anie.200501467

Thin bismuth film as a template for pentacene growth
journal, January 2005

  • Sadowski, J. T.; Nagao, T.; Yaginuma, S.
  • Applied Physics Letters, Vol. 86, Issue 7
  • DOI: 10.1063/1.1865350

2D Networks of Rhombic-Shaped Fused Dehydrobenzo[12]annulenes: Structural Variations under Concentration Control
journal, December 2009

  • Tahara, Kazukuni; Okuhata, Satoshi; Adisoejoso, Jinne
  • Journal of the American Chemical Society, Vol. 131, Issue 48
  • DOI: 10.1021/ja904481j

Polymorphism and chiral expression in two-dimensional subphthalocyanine crystals on Au(111)
journal, January 2010

  • Jiang, Nan; Wang, Yeliang; Liu, Qi
  • Phys. Chem. Chem. Phys., Vol. 12, Issue 6
  • DOI: 10.1039/B918278K

Temperature-Triggered Chiral Self-Assembly of Achiral Molecules at the Liquid–Solid Interface
journal, November 2016

  • Cheng, Linxiu; Li, Yibao; Zhang, Chun-Yu
  • ACS Applied Materials & Interfaces, Vol. 8, Issue 46
  • DOI: 10.1021/acsami.6b10883

Chiral Ordering and Conformational Dynamics for a Class of Oligo-phenylene-ethynylenes on Au(111)
journal, May 2007

  • Busse, Carsten; Weigelt, Sigrid; Petersen, Lars
  • The Journal of Physical Chemistry B, Vol. 111, Issue 21
  • DOI: 10.1021/jp0707891

Quasi Chiral Phase Separation in a Two-Dimensional Orientationally Disordered System:  6-Nitrospiropyran on Au(111)
journal, April 2007

  • Huang, Tian; Hu, Zhenpeng; Zhao, Aidi
  • Journal of the American Chemical Society, Vol. 129, Issue 13
  • DOI: 10.1021/ja066521p

Chirality in Supramolecular Self-Assembled Monolayers of Achiral Molecules on Graphite:  Formation of Enantiomorphous Domains from Arachidic Anhydride
journal, April 2005

  • Tao, Feng; Bernasek, Steven L.
  • The Journal of Physical Chemistry B, Vol. 109, Issue 13
  • DOI: 10.1021/jp0452397

Globally homochiral assembly of two-dimensional molecular networks triggered by co-absorbers
journal, January 2013

  • Chen, Ting; Yang, Wen-Hong; Wang, Dong
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms2403

Adsorption and two-dimensional phases of a large polar molecule: Sub-phthalocyanine on Ag(111)
journal, September 2003


Self-assembly and conformation of tetrapyridyl-porphyrin molecules on Ag(111)
journal, May 2006

  • Auwärter, W.; Weber-Bargioni, A.; Riemann, A.
  • The Journal of Chemical Physics, Vol. 124, Issue 19
  • DOI: 10.1063/1.2194541

Selection of conformational states in surface self-assembly for a molecule with eight possible pairs of surface enantiomers
journal, January 2016

  • Nuermaimaiti, A.; S-Falk, V.; Cramer, J. L.
  • Chemical Communications, Vol. 52, Issue 97
  • DOI: 10.1039/C6CC06876F

Chiral structures of lander molecules on Cu(100)
journal, March 2004


Coverage Driven Formation of Homochiral Domains of an Achiral Molecule on Au(111)
journal, October 2010

  • Gopakumar, Thiruvancheril G.; Matino, Francesca; Schwager, Bettina
  • The Journal of Physical Chemistry C, Vol. 114, Issue 42
  • DOI: 10.1021/jp106973p

Spatially resolved conductance of oriented C 60
journal, June 2008


Direct Visualization of Enantiospecific Substitution of Chiral Guest Molecules into Heterochiral Molecular Assemblies at Surfaces
journal, October 2007

  • Liu, Ning; Haq, Sam; Darling, George R.
  • Angewandte Chemie International Edition, Vol. 46, Issue 40
  • DOI: 10.1002/anie.200701675

Chiral Close-Packing of Achiral Star-Shaped Molecules on Solid Surfaces
journal, July 2006

  • Schöck, Maya; Otero, Roberto; Stojkovic, Sladjana
  • The Journal of Physical Chemistry B, Vol. 110, Issue 26
  • DOI: 10.1021/jp0619437

Orbital Specific Chirality and Homochiral Self-Assembly of Achiral Molecules Induced by Charge Transfer and Spontaneous Symmetry Breaking
journal, September 2010


Chiral Kagomé Lattice from Simple Ditopic Molecular Bricks
journal, September 2008

  • Schlickum, U.; Decker, R.; Klappenberger, F.
  • Journal of the American Chemical Society, Vol. 130, Issue 35
  • DOI: 10.1021/ja8028119

Self-Assembly of Chiral Molecular Honeycomb Networks on Au(111)
journal, July 2008

  • Xiao, Wende; Feng, Xinliang; Ruffieux, Pascal
  • Journal of the American Chemical Society, Vol. 130, Issue 28
  • DOI: 10.1021/ja7106542

Complex Interplay and Hierarchy of Interactions in Two-Dimensional Supramolecular Assemblies
journal, December 2010

  • Cañas-Ventura, Marta E.; Aït-Mansour, Kamel; Ruffieux, Pascal
  • ACS Nano, Vol. 5, Issue 1
  • DOI: 10.1021/nn102164g

Chiral Pinwheel Clusters Lacking Local Point Chirality
journal, April 2012


Buckybowls on Metal Surfaces: Symmetry Mismatch and Enantiomorphism of Corannulene on Cu(110)
journal, November 2007

  • Parschau, Manfred; Fasel, Roman; Ernst, Karl-Heinz
  • Angewandte Chemie International Edition, Vol. 46, Issue 43
  • DOI: 10.1002/anie.200700610

CHIRAL SUPRAMOLECULAR SELF-ASSEMBLY OF 2,2’:6’,2”-TERPYRIDINE-4’-CARBOXYLIC ACID MOLECULES CHEMICALLY ADSORBED ON Cu(111)
journal, November 2016


An aromatic coupling motif for two-dimensional supramolecular architectures
journal, January 2008

  • Treier, Matthias; Ruffieux, Pascal; Gröning, Pierangelo
  • Chemical Communications, Issue 38
  • DOI: 10.1039/b809618j

Chiral recognition of zinc phthalocyanine on Cu(100) surface
journal, February 2012

  • Chen, Feng; Chen, Xiu; Liu, Lacheng
  • Applied Physics Letters, Vol. 100, Issue 8
  • DOI: 10.1063/1.3685713

Self-assembled monolayers of thiols and dithiols on gold: new challenges for a well-known system
journal, January 2010

  • Vericat, C.; Vela, M. E.; Benitez, G.
  • Chemical Society Reviews, Vol. 39, Issue 5
  • DOI: 10.1039/b907301a

Hydrolytic and Thermal Stability of Organic Monolayers on Various Inorganic Substrates
journal, May 2014

  • Bhairamadgi, Nagendra S.; Pujari, Sidharam P.; Trovela, Florencio Gerardo
  • Langmuir, Vol. 30, Issue 20
  • DOI: 10.1021/la500533f

Control and stability of self-assembled monolayers under biosensing conditions
journal, January 2011

  • Seitz, Oliver; Fernandes, Poornika G.; Tian, Ruhai
  • Journal of Materials Chemistry, Vol. 21, Issue 12
  • DOI: 10.1039/c1jm10132c