Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding

Mukherjee, Arijit; Sanz-Matias, Ana; Velpula, Gangamallaiah; Waghray, Deepali; Ivasenko, Oleksandr; Bilbao, Nerea; Harvey, Jeremy N.; Mali, Kunal S.; De Feyter, Steven

doi:10.1039/c8sc04499f

Title: Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding

Abstract

We test whether the similarities between halogen and hydrogen bonds could be used to design a surface-confined halogen-bond based network.

Authors:

^[1];

^[1]; Waghray, Deepali ^[1];

^[1];

^[1]

KU Leuven (Belgium)

Publication Date:: 2019-01-01

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1559200

Grant/Contract Number:: AC02-05CH11231

Resource Type:: Accepted Manuscript

Journal Name:: Chemical Science

Additional Journal Information:: Journal Volume: 10; Journal Issue: 13; Journal ID: ISSN 2041-6520

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Mukherjee, Arijit, Sanz-Matias, Ana, Velpula, Gangamallaiah, Waghray, Deepali, Ivasenko, Oleksandr, Bilbao, Nerea, Harvey, Jeremy N., Mali, Kunal S., and De Feyter, Steven. Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding.  United States: N. p., 2019. 
Web.  doi:10.1039/c8sc04499f.

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                    Mukherjee, Arijit, Sanz-Matias, Ana, Velpula, Gangamallaiah, Waghray, Deepali, Ivasenko, Oleksandr, Bilbao, Nerea, Harvey, Jeremy N., Mali, Kunal S., & De Feyter, Steven. Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding.  United States.  https://doi.org/10.1039/c8sc04499f

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                    Mukherjee, Arijit, Sanz-Matias, Ana, Velpula, Gangamallaiah, Waghray, Deepali, Ivasenko, Oleksandr, Bilbao, Nerea, Harvey, Jeremy N., Mali, Kunal S., and De Feyter, Steven. Tue .  
"Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding".  United States.  https://doi.org/10.1039/c8sc04499f.  https://www.osti.gov/servlets/purl/1559200.

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@article{osti_1559200,

  title        = {Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding},

  author       = {Mukherjee, Arijit and Sanz-Matias, Ana and Velpula, Gangamallaiah and Waghray, Deepali and Ivasenko, Oleksandr and Bilbao, Nerea and Harvey, Jeremy N. and Mali, Kunal S. and De Feyter, Steven},

  abstractNote = {We test whether the similarities between halogen and hydrogen bonds could be used to design a surface-confined halogen-bond based network.},

  doi          = {10.1039/c8sc04499f},

  journal      = {Chemical Science},

  number       = 13,

  volume       = 10,

  place        = {United States},

  year         = {2019},

  month        = {1}

}

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Works referencing / citing this record:

Forty years of progress in the study of the hydrogen bond
journal, June 2019

Scheiner, Steve
Structural Chemistry, Vol. 30, Issue 4
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The Hydrogen Bond: A Hundred Years and Counting
journal, November 2019

Scheiner, Steve
Journal of the Indian Institute of Science, Vol. 100, Issue 1
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Metal-involving halogen bond Ar–I⋯[d _z2 Pt ^II ] in a platinum acetylacetonate complex
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Rozhkov, Anton V.; Ivanov, Daniil M.; Novikov, Alexander S.
CrystEngComm, Vol. 22, Issue 3
DOI: 10.1039/c9ce01568j

Cooperation and competition of hydrogen and halogen bonds in 2D self-assembled nanostructures based on bromine substituted coumarins
journal, January 2019

Zha, Bao; Li, Jinxing; Wu, Juntian
New Journal of Chemistry, Vol. 43, Issue 44
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Revealing the role of different nitrogen functionalities in the drug delivery performance of graphene quantum dots: a combined density functional theory and molecular dynamics approach
journal, January 2019

Vatanparast, Morteza; Shariatinia, Zahra
Journal of Materials Chemistry B, Vol. 7, Issue 40
DOI: 10.1039/c9tb00971j

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Title: Halogenated building blocks for 2D crystal engineering on solid surfaces: lessons from hydrogen bonding

Abstract

Citation Formats

Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis journal, November 1995

Interplay between Halogen and Hydrogen Bonds in 2D Self-Assembly on the Gold Surface: A First-Principles Investigation journal, October 2017

Concentration dependent halogen-bond density in the 2D self-assembly of a thienophenanthrene derivative at the aliphatic acid/graphite interface journal, January 2014

The Halogen Bond journal, January 2016

Treatment of Halogen Bonding in the OPLS-AA Force Field: Application to Potent Anti-HIV Agents journal, March 2012

Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning journal, January 2015

Mastering fundamentals of supramolecular design with carboxylic acids. Common lessons from X-ray crystallography and scanning tunneling microscopy journal, January 2011

Hydrogen Bonding Versus van der Waals Interactions: Competitive Influence of Noncovalent Interactions on 2D Self-Assembly at the Liquid-Solid Interface journal, November 2010

An efficient newton-like method for molecular mechanics energy minimization of large molecules journal, October 1987

Charge Density Analysis and Topological Properties of Hal 3 -Synthons and Their Comparison with Competing Hydrogen Bonds journal, October 2012

Toward Two-Dimensional Supramolecular Control of Hydrogen-Bonded Arrays: The Case of Isophthalic Acids journal, November 2003

Six Different Assemblies from One Building Block: Two-Dimensional Crystallization of an Amide Amphiphile journal, August 2010

Selective Adsorption at Graphite/Hydrocarbon Interfaces journal, January 1970

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Frontiers of supramolecular chemistry at solid surfaces journal, January 2017

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Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering journal, May 2015

Chains, Ladders, and Two-Dimensional Sheets with Halogenċ Halogen and Halogenċ Hydrogen Interactions journal, April 1997

Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different journal, May 2014

Self-Assembly Behavior of Alkylated Isophthalic Acids Revisited: Concentration in Control and Guest-Induced Phase Transformation journal, December 2014

Hydrogen-Bonding versus van der Waals Interactions in Self-Assembled Monolayers of Substituted Isophthalic Acids journal, December 2010

Surface-Based Supramolecular Chemistry Using Hydrogen Bonds journal, October 2014

Role of Substrate in Directing the Self-Assembly of Multicomponent Supramolecular Networks at the Liquid–Solid Interface journal, August 2012

Hydrogen bonding control of self-assembly: Simple isophthalic acid derivatives form cyclic hexameric aggregates journal, May 1994

Two-dimensional crystal engineering using halogen and hydrogen bonds: towards structural landscapes journal, January 2017

Combined Diffraction and Density Functional Theory Calculations of Halogen-Bonded Cocrystal Monolayers journal, November 2013

Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity journal, September 2009

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene journal, February 2015

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals journal, July 2007

Substrate Effects in the Supramolecular Self-Assembly of 2,4,6-Tris(4-bromophenyl)-1,3,5-triazine on Graphite and Graphene journal, May 2018

Understanding the Behavior of Halogens as Hydrogen Bond Acceptors journal, July 2001

Solvent effects on two-dimensional molecular self-assemblies investigated by using scanning tunneling microscopy journal, April 2009

Natural Bond Orbitals and the Nature of the Hydrogen Bond journal, February 2017

Formation of Halogen Bond-Based 2D Supramolecular Assemblies by Electric Manipulation journal, May 2015

One Building Block, Two Different Supramolecular Surface-Confined Patterns: Concentration in Control at the Solid–Liquid Interface journal, April 2008

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The Hydrogen Bond: A Hundred Years and Counting journal, November 2019

Metal-involving halogen bond Ar–I⋯[d z2 Pt II ] in a platinum acetylacetonate complex journal, January 2020

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Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
journal, November 1995

Interplay between Halogen and Hydrogen Bonds in 2D Self-Assembly on the Gold Surface: A First-Principles Investigation
journal, October 2017

Concentration dependent halogen-bond density in the 2D self-assembly of a thienophenanthrene derivative at the aliphatic acid/graphite interface
journal, January 2014

The Halogen Bond
journal, January 2016

Treatment of Halogen Bonding in the OPLS-AA Force Field: Application to Potent Anti-HIV Agents
journal, March 2012

Supramolecular hierarchy among halogen and hydrogen bond donors in light-induced surface patterning
journal, January 2015

Mastering fundamentals of supramolecular design with carboxylic acids. Common lessons from X-ray crystallography and scanning tunneling microscopy
journal, January 2011

Hydrogen Bonding Versus van der Waals Interactions: Competitive Influence of Noncovalent Interactions on 2D Self-Assembly at the Liquid-Solid Interface
journal, November 2010

An efficient newton-like method for molecular mechanics energy minimization of large molecules
journal, October 1987

Charge Density Analysis and Topological Properties of Hal ₃ -Synthons and Their Comparison with Competing Hydrogen Bonds
journal, October 2012

Toward Two-Dimensional Supramolecular Control of Hydrogen-Bonded Arrays: The Case of Isophthalic Acids
journal, November 2003

Six Different Assemblies from One Building Block: Two-Dimensional Crystallization of an Amide Amphiphile
journal, August 2010

Selective Adsorption at Graphite/Hydrocarbon Interfaces
journal, January 1970

Concentration and Coverage Dependent Adlayer Structures: From Two-Dimensional Networks to Rotation in a Bearing
journal, November 2009

Frontiers of supramolecular chemistry at solid surfaces
journal, January 2017

Directing two-dimensional molecular crystallization using guest templates
journal, January 2008

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journal, June 2013

Building upon Supramolecular Synthons: Some Aspects of Crystal Engineering
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Chains, Ladders, and Two-Dimensional Sheets with Halogenċ Halogen and Halogenċ Hydrogen Interactions
journal, April 1997

Halogen Bonds in Crystal Engineering: Like Hydrogen Bonds yet Different
journal, May 2014

Self-Assembly Behavior of Alkylated Isophthalic Acids Revisited: Concentration in Control and Guest-Induced Phase Transformation
journal, December 2014

Hydrogen-Bonding versus van der Waals Interactions in Self-Assembled Monolayers of Substituted Isophthalic Acids
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Surface-Based Supramolecular Chemistry Using Hydrogen Bonds
journal, October 2014

Role of Substrate in Directing the Self-Assembly of Multicomponent Supramolecular Networks at the Liquid–Solid Interface
journal, August 2012

Hydrogen bonding control of self-assembly: Simple isophthalic acid derivatives form cyclic hexameric aggregates
journal, May 1994

Two-dimensional crystal engineering using halogen and hydrogen bonds: towards structural landscapes
journal, January 2017

Combined Diffraction and Density Functional Theory Calculations of Halogen-Bonded Cocrystal Monolayers
journal, November 2013

Molecular and Supramolecular Networks on Surfaces: From Two-Dimensional Crystal Engineering to Reactivity
journal, September 2009

Substrate Effects in the Supramolecular Assembly of 1,3,5-Benzene Tricarboxylic Acid on Graphite and Graphene
journal, February 2015

The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals
journal, July 2007

Substrate Effects in the Supramolecular Self-Assembly of 2,4,6-Tris(4-bromophenyl)-1,3,5-triazine on Graphite and Graphene
journal, May 2018

Understanding the Behavior of Halogens as Hydrogen Bond Acceptors
journal, July 2001

Solvent effects on two-dimensional molecular self-assemblies investigated by using scanning tunneling microscopy
journal, April 2009

Natural Bond Orbitals and the Nature of the Hydrogen Bond
journal, February 2017

Formation of Halogen Bond-Based 2D Supramolecular Assemblies by Electric Manipulation
journal, May 2015

One Building Block, Two Different Supramolecular Surface-Confined Patterns: Concentration in Control at the Solid–Liquid Interface
journal, April 2008

Crystal Engineering: From Molecule to Crystal
journal, June 2013

One Building Block, Two Different Supramolecular Surface-Confined Patterns: Concentration in Control at the Solid–Liquid Interface
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The Hydrogen Bond: A Hundred Years and Counting
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Metal-involving halogen bond Ar–I⋯[d _z2 Pt ^II ] in a platinum acetylacetonate complex
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