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

doi:10.1021/jo501903n

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

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

66 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 language	English
Pages (from-to)	9735-9739
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	79
Issue number	20
DOIs	https://doi.org/10.1021/jo501903n
Publication status	Published - 2014 Oct 17

ASJC Scopus subject areas

Organic Chemistry

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

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).",

author = "Xue, {Jing Yang} and Koki Ikemoto and Norihisa Takahashi and Tomoo Izumi and Hideo Taka and Hiroshi Kita and Sota Sato and Hiroyuki Isobe",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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doi = "10.1021/jo501903n",

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T1 - Cyclo-meta-phenylene revisited

T2 - Nickel-mediated synthesis, molecular structures, and device applications

AU - Xue, Jing Yang

AU - Ikemoto, Koki

AU - Takahashi, Norihisa

AU - Izumi, Tomoo

AU - Taka, Hideo

AU - Kita, Hiroshi

AU - Sato, Sota

AU - Isobe, Hiroyuki

PY - 2014/10/17

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AB - 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).

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

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