title: Self-assembly of pyridinium-functionalized anthracenes: molecular-skeleton-directed formation of microsheets and microtubes.
abstract: Two amphiphilic regioisomers, 9-AP (1-[11-(9-anthracenylmethoxy)-11-oxoundecyl]pyridinium bromide), and 2-AP (1-[11-(2-anthracenyl methoxy)-11-oxoundecyl]pyridinium bromide), were synthesized and their assembly behaviors were studied. Due to the anisotropic features of the anthracene structure, different substituted positions on the anthracene ring lead 9-AP and 2-AP to adapt "shaver" and "spatula"-like molecular shapes, respectively, which consequently dictate the structure of their final assemblies. While "shaver"-shaped 9-AP assembled into microsheets, driven by π-π interactions, "spatula"-shaped 2-AP assembled into microtubular structures, promoted primarily by charge-transfer interactions.
authors.affiliation: Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC, 29208 (USA).
authors.forename: Jun
authors.initials: J
authors.lastname: Hu
authors.forename: Peiyi
authors.initials: P
authors.lastname: Wang
authors.forename: Yuan
authors.initials: Y
authors.lastname: Lin
authors.forename: Jidong
authors.initials: J
authors.lastname: Zhang
authors.forename: Mark
authors.initials: M
authors.lastname: Smith
authors.forename: Perry J
authors.initials: PJ
authors.lastname: Pellechia
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.forename: Baoan
authors.initials: B
authors.lastname: Song
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
mesh_terms: D000873:Anthracenes / Q000737:chemistry*; D015394:Molecular Structure; D013501:Surface-Active Agents / Q000737:chemistry*
chemical_list: D000873:Anthracenes; D013501:Surface-Active Agents; C034020:anthracene
keywords: amphiphiles; charge transfer; molecular engineering; pi-pi interactions; self-assembly