Self-assembly of semifluorinated minidendrons attached to electron-acceptor groups into pyramidal columns

Virgil Percec, Emad Aqad, Mihai Peterca, Mohammad R. Imam, Martin Glodde, Tusha K. Bera, Yoshiko Miura, Venkatachalapathy S.K. Balagurusamy, Paul C. Ewbank, Frank Würthner, Paul A. Heiney

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

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 arc reported. Dendrons attached to small electron-acceptor molecules mediate their self-assembly into π-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 π-stacks that have the long axis of the acceptors parallel to the long axis of the supramolecular pyramidal column. All supra_molecular 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 π-type electroactive groups mediated by semifluorinated dendrons and assesses the scope and limitations of this supramolecular strategy.

Original languageEnglish
Pages (from-to)3330-3345
Number of pages16
JournalChemistry - A European Journal
Volume13
Issue number12
DOIs
Publication statusPublished - Jun 21 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

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