Carboxylic Acids: Versatile Building Blocks and Mediators for Two-Dimensional Supramolecular Self-Assembly
- 19 May 2009
- journal article
- Published by American Chemical Society (ACS) in Langmuir
- Vol. 25 (19), 11307-11321
- https://doi.org/10.1021/la900785f
Abstract
Two-dimensional (2D) supramolecular self-assembly of various organic molecules at the liquid−solid interface is presented and discussed with a focus on compounds that are primarily functionalized by carboxylic groups. The main analytical tool utilized is scanning tunneling microscopy (STM), a high-resolution real-space technique capable of readily providing full crystallographic information (i.e., not only lattice parameters but also number, type, and orientation of molecules within the unit cell). Carboxylic groups are of particular interest because their combined donor and acceptor character with regard to hydrogen bonds provides reliable intermolecular cross-linking, thereby facilitating the self-assembly of well-ordered, stable monolayers. By means of various homomeric (monomolecular) and heteromeric (here, bimolecular) examples, this feature article illustrates the influence of both molecular structure and external conditions (type of solvent, concentration, etc.) on monolayer self-assembly at the liquid−solid interface. A very intriguing aspect of interfacial self-assembly is that many systems are thermodynamically controlled (i.e., adsorbed molecules at the surface are in equilibrium with molecules dissolved in the supernatant liquid phase). This offers the unique possibility not only to steer the system reliably by intensive thermodynamic parameters such as temperature and concentration but also to gain fundamental knowledge about decisive processes and steps in supramolecular self-assembly.Keywords
This publication has 70 references indexed in Scilit:
- Recent Progress in Electrochemical Surface Science with Atomic and Molecular LevelsElectrochemistry, 2009
- Scanning Tunneling Microscopy and Orbital-Mediated Tunneling Spectroscopy of N,N′-Dioctyl-1,8:4,5-naphthalenediimide Adsorbed on Highly Ordered Pyrolytic Graphite from Various Solvents and in Different EnvironmentsThe Journal of Physical Chemistry C, 2008
- Giant molecular spoked wheels in giant voids: two-dimensional molecular self-assembly goes bigChemical Communications, 2008
- Molecular Geometry Directed Kagomé and Honeycomb Networks: Toward Two-Dimensional Crystal EngineeringJournal of the American Chemical Society, 2006
- Self-Assembly at the Liquid/Solid Interface: STM RevealsThe Journal of Physical Chemistry B, 2005
- The Hydrogen Bond in the Solid StateAngewandte Chemie-International Edition, 2002
- Substrate Mediated Long-Range Oscillatory Interaction between Adatoms: CuCu(111)Physical Review Letters, 2000
- Estimating the Entropic Cost of Self-Assembly of Multiparticle Hydrogen-Bonded Aggregates Based on the Cyanuric Acid·Melamine LatticeThe Journal of Organic Chemistry, 1998
- Ab Initio Calculations of Supramolecular Recognition Modes. Cyclic versus Noncyclic Hydrogen Bonding in the Formic Acid/Formamide SystemThe Journal of Physical Chemistry, 1994
- Molecular Self-Assembly and Nanochemistry: a Chemical Strategy for the Synthesis of NanostructuresScience, 1991