Cyclo-meta-phenylene revisited: Nickel-mediated synthesis, molecular structures, and device applications

Jing Yang Xue, Koki Ikemoto, Norihisa Takahashi, Tomoo Izumi, Hideo Taka, Hiroshi Kita, Sota Sato, Hiroyuki Isobe

Research output: Contribution to journalArticlepeer-review

55 Citations (Scopus)

Abstract

From a one-pot nickel-mediated Yamamoto-type coupling reaction of m-dibromobenzene, five congeners of [n]cyclo-meta-phenylenes were synthesized and fully characterized. The [n]cyclo-meta-phenylenes possessed a commonly shared arylene unit and intermolecular contacts but varied in packing structures in the crystalline solid state. Columnar assembly of larger congeners yielded nanoporous crystals with carbonaceous walls to capture minor protic or aliphatic solvent molecules. The concise and scalable synthesis allowed exploration of the macrocyclic hydrocarbons as bipolar charge carrier transport materials in organic lightemitting diode devices. (Figure Presented).

Original languageEnglish
Pages (from-to)9735-9739
Number of pages5
JournalJournal of Organic Chemistry
Volume79
Issue number20
DOIs
Publication statusPublished - 2014 Oct 17

ASJC Scopus subject areas

  • Organic Chemistry

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