title: Anthraquinone derivatives as electron-acceptors with liquid crystalline properties.
abstract: Dialkoxy derivatives of anthraquinone (AQ), dicyano-anthraquinone (DCAQ) and tetracyanoanthraquinone (TCAQ) were synthesized and their associated electrochemical, optical and self-assembling properties were investigated as candidates for n-type materials. AQ shows UV absorption features, whereas both DCAQ and TCAQ exhibit bathochromic and hyperchromic electronic transitions into the visible region. The electron accepting strength of the three compounds was established by cyclic voltammetry as -1.52 V, -1.3 V and -0.9 V vs. ferrocene/ferricenium for AQ, DCAQ and TCAQ, respectively. All three quinones displayed quasireversible, two sequential one-electron transfer redox reactions. DFT calculations of DCAQ and TCAQ demonstrate structural changes upon reduction, which is supported by spectroelectrochemical experiments. Furthermore, the structural changes result in different absorption profiles and show potential as electrochromic materials. Finally, both AQ and DCAQ show liquid crystalline phases and importantly, DCAQ exhibits both a smectic liquid crystalline and a soft crystal phase between -6 °C and 85 °C, which offers promise as a self-assembling n-type material.
authors.affiliation: Department of Chemistry, University of Calgary, Alberta, Canada.
authors.forename: Amy E
authors.initials: AE
authors.lastname: Murschell
authors.forename: Wang Hay
authors.initials: WH
authors.lastname: Kan
authors.forename: Venkataraman
authors.initials: V
authors.lastname: Thangadurai
authors.forename: Todd C
authors.initials: TC
authors.lastname: Sutherland
mesh_terms: D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry*; D004563:Electrochemistry; D004583:Electrons; D050866:Liquid Crystals / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D000880:Anthraquinones