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Functionalized Redox Systems pp 51–109Cite as

π-Conjugated Systems with Coenzyme PQQ, Polyanilines or Quinonediimines, and Sumanene

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Abstract

Coenzyme PQQ serves as a catalyst or mediator in redox reactions under molecular oxygen. Polyanilines and quinonediimines are found to serve as redox-active organo catalysts for proton-conjugated electron transfer. The hybrid d,π-conjugated systems composed of transition metals and π-conjugated compounds as redox-active ligands are constructed and applied to the catalytic oxidation reaction. Chirality induction of the π-conjugated chain is attained through chiral complexation. The d,π-conjugated complex is reduced to small and well-dispersed nanoparticles. Oxidative reactions are induced by transition metal nanoparticles and polyanilines as a redox-active mediator. Imidovanadium compounds bearing the π-conjugated substituents at the N-position are characterized.

Bowl-shaped π-conjugated “sumanene” is synthesized for the first time. X-ray single crystal structural and conductivity analyses reveal its columnar stacking with n-type electron transportation ability. Bowl-to-bowl inversion behavior and generation of benzylic anions are studied. Short synthesis of extended π bowls is achieved utilizing bowl-shaped sumanene. The concave or convex π-bent surface is demonstrated to serve as a ligand to give the corresponding d,π-conjugated bowl complex selectively.

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Abbreviations

AFM:

Atomic force microscope

BN:

Binaphthyl

bpy:

2,2′-Bipyridine

BuLi:

Butyllithium

CD:

Circular dichroism

Cp:

Cyclopentadienyl

Cp*:

1,2,3,4,5-Pentamethylcyclopentadienyl

CTAB:

Cetyltrimethylammonium bromide

DA:

Diamine

DABCO:

1,4-Diazabicyclo[2.2.2]octane

DDQ:

2,3-Dichloro-5,6-dicyano-p-benzoquinone

DMH:

N,N-dimethylhydrazine

en:

Ethylenediamine

EXSY:

Exchange spectroscopy

Fc:

Ferrocene

ICD:

Induced circular dichroism

iPr:

Isopropyl

K c :

Equilibrium constant

Me:

Methyl

MeCN:

Acetonitrile

NGCs:

Nitrogen-doped graphitic carbons

NMR:

Nuclear magnetic resonance

NOE:

Nuclear Overhauser effect

OAc:

Acetate

OEt:

Ethoxide

OiPr:

Isopropoxide

PD:

Phenylenediamine

Ph:

Phenyl

PMAS:

Poly(2-methoxyaniline-5-sulfonic acid)

POT:

Poly(o-toluidine)

ppm:

Parts per million

PQQ:

Pyrroloquinoline quinone

PQQTME:

Trimethyl 4,5-dihydro-4,5-dioxo-lH-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate

QD:

Quinonediimine

SQ:

Semiquinonediimine radical anion

TEA:

Triethanolamine

THF:

Tetrahydrofuran

TPP:

Tetraphenylporphyrin

tpy:

2,2′:6′,2″-Terpyridine

TRMC:

Time-resolved microwave conductivity

UV–vis:

Ultraviolet–visible

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Authors and Affiliations

  1. Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamada-oka, Suita, Osaka, 565-0871, Japan

    Toshikazu Hirao, Toshiyuki Moriuchi & Toru Amaya

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  1. Toshikazu Hirao
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  2. Toshiyuki Moriuchi
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  3. Toru Amaya
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Correspondence to Toshikazu Hirao .

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  1. Osaka University, Osaka, Japan

    Toshikazu Hirao

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Hirao, T., Moriuchi, T., Amaya, T. (2015). π-Conjugated Systems with Coenzyme PQQ, Polyanilines or Quinonediimines, and Sumanene. In: Hirao, T. (eds) Functionalized Redox Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55306-9_3

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