Linear Acene Proton Conductors for Molecular Protonics

2017 Fiscal Year Annual Research Report

• Project/Area Number: 15K13684
• Research Institution: National Institute for Materials Science
• Principal Investigator: HILL Jonathan 国立研究開発法人物質・材料研究機構, 国際ナノアーキテクトニクス研究拠点, 主席研究員 (30421431)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: Pyrazinacene / Tautomerism / Proton conductor

Outline of Annual Research Achievements

The synthesis of monomer units was successfully concluded with availability acenes containing 8, 10 and 14 nitrogen atoms. This includes important new compounds octaazatetracene, decaazapentacene and tetradecaazaheptacene. These compounds were shown to exhibit expected proton mobility using crystal structure and NMR spectroscopy. Interactions with bases and acids was investigated revealing large variations in properties depending on proton processes. Compounds were found to undergo light-coupled protic processes. Also, compounds were incorporated into dye-sensitized solar cells with modest efficiency. Decaazapentacene was synthesized in situ on a surface forming interesting self-assembled structures.

Research Products

• [Journal Article] Phenanthroline-fused Pyrazinacenes: One-pot Synthesis, Tautomerization and a Ru(II)(2,2’-bpy)2 Derivative (2018)
  • Author(s): Pavel Svec, Whitney A. Webre, Gary J. Richards, Jan Labuta, Yutaka Wakayama, David Miklik, Paul A. Karr, Toshiyuki Mori, Katsuhiko Ariga, Francis D’Souza and Jonathan P. Hill
  • Journal Title: European Journal of Inorganic Chemistry Volume: - Pages: -
  • DOI: 10.1002/ejic.201800283
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Structural Modulation of Chromic Response: Effects of Binding Site Blocking in a Conjugated Calix[4]pyrrole Chromophore (2018)
  • Author(s): Vaclav Brezina, Shinsuke Ishihara, Jan Lang, Lenka Hanykova, Katsuhiko Ariga, Jonathan P. Hill, Jan Labuta
  • Journal Title: ChemistryOpen Volume: - Pages: -
  • DOI: 10.1002/open.201800005
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Fluoride-ion-binding Promoted Photoinduced Charge Separation in a Self-assembled C60 Alkyl Cation Bound Bis-crown Ether-oxoporphyrinogen Supramolecule (2018)
  • Author(s): Whitney A. Webre, Habtom B. Gobeze, Shuai Shao, Paul A. Karr, Katsuhiko Ariga, Jonathan P. Hill, Francis D’Souza
  • Journal Title: Chemical Communications Volume: 54 Pages: 1351-1354
  • DOI: 10.1039/C7CC09524D
• [Presentation] Pyrazinacenes and Oxoporphyrinogens (2017)
  • Author(s): Jonathan P. Hill, David Miklik, Pavel Svec, Yoshitaka Matsushita, Jan Labuta, Shinsuke Ishihara, Francis D’Souza, Katsuhiko Ariga
  • Organizer: 231st Electrochemical Society Meeting
  • Int'l Joint Research / Invited
• [Presentation] Pyrazinacenes and Oxoporphyrinogens (2017)
  • Author(s): Jonathan P. Hill, David Miklik, Yoshitaka Matsushita, Jan Labuta, Katsuhiko Ariga
  • Organizer: Congress of the Slovak Chemical Society
  • Invited
• [Presentation] Pyrazinacenes, Porphyrins and Oxoporphyrinogens (2017)
  • Author(s): Jonathan P. Hill, Jan Labuta, Shinsuke Ishihara, David Miklik, Gary J. Richards and Katsuhiko Ariga
  • Organizer: International Conf. on Functional Nanomaterials and Nanotechnology
  • Invited