title: Self-assembly of semifluorinated minidendrons attached to electron-acceptor groups into pyramidal columns.
abstract: The synthesis and self-assembly of twelve semifluorinated first-generation dendrons or minidendrons attached to electron-acceptor (n-type) groups generated from various combinations of eight acceptors and three dendrons are reported. Dendrons attached to small electron-acceptor molecules mediate their self-assembly into pi-stacks located in the center of a supramolecular helical pyramidal column with the long axis of the acceptor perpendicular to the long axis of the column. Dendrons attached to large electron-acceptor molecules, such as perylene bisimide, mediate the assembly of their acceptors in an unprecedented arrangement of pi-stacks that have the long axis of the acceptors parallel to the long axis of the supramolecular pyramidal column. All supramolecular columns self-organize into various periodic columnar arrays that exhibit liquid-crystalline phases, crystalline phases, or a liquid-crystalline phase with enhanced intracolumnar order. The present study demonstrates the simplicity and the versatility of the concept of assembly of n-type electroactive groups mediated by semifluorinated dendrons and assesses the scope and limitations of this supramolecular strategy.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. percec@sas.upenn.edu
authors.forename: Virgil
authors.initials: V
authors.lastname: Percec
authors.forename: Emad
authors.initials: E
authors.lastname: Aqad
authors.forename: Mihai
authors.initials: M
authors.lastname: Peterca
authors.forename: Mohammad R
authors.initials: MR
authors.lastname: Imam
authors.forename: Martin
authors.initials: M
authors.lastname: Glodde
authors.forename: Tusha K
authors.initials: TK
authors.lastname: Bera
authors.forename: Yoshiko
authors.initials: Y
authors.lastname: Miura
authors.forename: Venkatachalapathy S K
authors.initials: VS
authors.lastname: Balagurusamy
authors.forename: Paul C
authors.initials: PC
authors.lastname: Ewbank
authors.forename: Frank
authors.initials: F
authors.lastname: Würthner
authors.forename: Paul A
authors.initials: PA
authors.lastname: Heiney