skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

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

Journal Article · · Chemical Science
DOI:https://doi.org/10.1039/c8sc04499f· OSTI ID:1559200

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

Research Organization:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
Grant/Contract Number:
AC02-05CH11231
OSTI ID:
1559200
Journal Information:
Chemical Science, Vol. 10, Issue 13; ISSN 2041-6520
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 26 works
Citation information provided by
Web of Science

References (38)

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
Synthon Modularity in Cocrystals of 4-Bromobenzamide with n -Alkanedicarboxylic Acids: Type I and Type II Halogen···Halogen Interactions journal June 2013
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
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 journal April 2008

Cited By (5)

Forty years of progress in the study of the hydrogen bond journal June 2019
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
Cooperation and competition of hydrogen and halogen bonds in 2D self-assembled nanostructures based on bromine substituted coumarins journal January 2019
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

Similar Records

Interrogating the Interplay between Hydrogen and Halogen Bonding in Graphitic Carbon Nitride Building Blocks
Journal Article · Sat Dec 12 00:00:00 EST 2020 · Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory · OSTI ID:1559200

Shedding Light on the Vibrational Signatures in Halogen‐Bonded Graphitic Carbon Nitride Building Blocks
Journal Article · Fri Jan 20 00:00:00 EST 2023 · ChemPhysChem · OSTI ID:1559200

Theoretical, Solid-State, and Solution Quantification of the Hydrogen Bond-Enhanced Halogen Bond
Journal Article · Mon Dec 21 00:00:00 EST 2020 · Angewandte Chemie (International Edition) · OSTI ID:1559200