title: Distinct differences in self-assembly of aromatic linear dicarboxylic acids.
abstract: Self-assembly into two-dimensionally ordered supramolecular structures of three aromatic dicarboxylic acids-2,6-naphthalenedicarboxylic acid (NDA), 4,4'-biphenyldicarboxylic acid (BPDA), and 4,4'-stilbenedicarboxylic acid (SDA)-is studied at the liquid-solid interface by scanning tunneling microscopy. All compounds possess structural similarities, namely, two interconnected aromatic moieties and functionalization through two carboxylic groups in linear configuration. For all molecules, ordered monolayers were observed on a graphite substrate, and the resulting structures can be described as a dense packing of one-dimensionally hydrogen-bonded rows. However, concerning the stability of the adsorbate layers, the average domain size, and the degree of order, distinct differences were noticed. Supported by density functional theory (DFT) calculations, these differences are analyzed and explained as a consequence of molecular structure, adsorption geometry, and adsorption energy.
authors.affiliation: Department for Earth and Environmental Sciences, Ludwig-Maximilians-University and Center for NanoScience (CeNS), Theresienstrasse 41, DE-80333 Munchen, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Heininger
authors.forename: Lorenz
authors.initials: L
authors.lastname: Kampschulte
authors.forename: Wolfgang M
authors.initials: WM
authors.lastname: Heckl
authors.forename: Markus
authors.initials: M
authors.lastname: Lackinger
mesh_terms: D000327:Adsorption; D001713:Biphenyl Compounds / Q000737:chemistry*; D003998:Dicarboxylic Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D016252:Microscopy, Scanning Tunneling; D008956:Models, Chemical; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010316:Particle Size; D013267:Stilbenes / Q000737:chemistry*; D013499:Surface Properties
chemical_list: C535263:4,4'-biphenyldicarboxylic acid; C535264:4,4'-stilbenedicarboxylic acid; D001713:Biphenyl Compounds; D003998:Dicarboxylic Acids; D009281:Naphthalenes; D013267:Stilbenes; C109064:2,6-naphthalenedicarboxylic acid