title: Self-assembly of isomeric monofunctionalized thiophenes.
abstract: Controlling the self-assembly of thiophene-containing molecules and polymers requires a strong fundamental understanding of the relationship between molecular features and structure-directing forces. Here, the effects of ring-substitution position on the two-dimensional self-assembly of monosubstituted thiophenes at the phenyloctane/HOPG interface are studied using scanning tunneling microscopy (STM). The influence of π···π-stacking, hydrogen-bonding, and alkyl-chain interactions are explored computationally. Alteration of the amide attachment point from the 2- to the 3-position induces transformation from head-to-tail packing to head-to-head packing. This may be attributed to canceling of lateral dipoles.
authors.affiliation: Department of Chemistry, Franklin & Marshall College, Lancaster, Pennsylvania 17604, United States.
authors.forename: Laura E
authors.initials: LE
authors.lastname: Heller
authors.forename: Julianne
authors.initials: J
authors.lastname: Whitleigh
authors.forename: Danielle F
authors.initials: DF
authors.lastname: Roth
authors.forename: Elisabeth M
authors.initials: EM
authors.lastname: Oherlein
authors.forename: Felicia R
authors.initials: FR
authors.lastname: Lucci
authors.forename: Kristopher J
authors.initials: KJ
authors.lastname: Kolonko
authors.forename: Katherine E
authors.initials: KE
authors.lastname: Plass
mesh_terms: D006860:Hydrogen Bonding; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011108:Polymers; D013876:Thiophenes