The First Pentahaptofullerene Metal Complexes

Sawamura, Masaya; Iikura, Hitoshi; Nakamura, Eiichi

doi:10.1021/ja962681x

Cited by 284 publications

(146 citation statements)

References 8 publications

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“…The reaction was first found to take place in 3% yield but eventually improved to give the product in 98% yield, as determined for an analytically pure sample [2]. The reaction is general for various aryl [3] and alkenyl groups as well as for methyl group [4].…”

Section: Quantitative Penta-and Tri-addition To Fullerenesmentioning

confidence: 87%

Chemistry of η5-fullerene metal complexes

Nakamura

Sawamura

2001

Pure and Applied Chemistry

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Treatment of [60]fullerene with an organocopper reagent converts one of the pentagons of the fullerene into cyclopentadienyl anion through addition of five organic groups on every peripheral carbon atom surrounding the pentagon. Similar treatment of [70]fullerene afforded indenyl anion through regioselective tri-addition of the organic group. These anionic moieties strongly interact with the remainder of the fullerene π-system, and provide unique opportunity for exploration of organometallic chemistry of a new class of metal cyclopentadienides.

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Section: Quantitative Penta-and Tri-addition To Fullerenesmentioning

confidence: 87%

Chemistry of η5-fullerene metal complexes

Nakamura

Sawamura

2001

Pure and Applied Chemistry

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“…36,37 Nevertheless, the curvature can be ameliorated by functionalization, [37][38][39] and this has allowed the preparation of organometallic fullerene derivatives. 38,40 In C 60 the -orbital axis vectors are directed away from the center of the respective rings and make angles of 16.3 o (POAV2) to a normal to the plane of the five-membered rings and 25.8 o (POAV2) to a normal to the plane of the six-membered rings; hence, hexahapto-( 6 ) coordination is even more strongly disfavored than pentahapto-( 5 ) complexation.…”

Section: Introductionmentioning

confidence: 99%

Organometallic chemistry of extended periodic π-electron systems: hexahapto-chromium complexes of graphene and single-walled carbon nanotubes

et al. 2011

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“…PAC 60 s (1a-d) were synthesized in the same way with Nakamura et al [28][29][30] The chemical structures are drawn in Figure 1. They were identified by 1 H-NMR, 13 C-NMR, and MALDI-TOF-MASS.…”

Section: Methodsmentioning

confidence: 99%

“…[60]fullerenes (PAC 60 ) developed by Nakamura et al [28][29][30] are appropriate motifs, due to their facile synthetic procedure with a good yield. We have also investigated photochemical properties of PAC 60 in solution by transient absorption spectroscopy (TAS) and photoelectric conversion in film state by time-resolved microwave conductivity (TRMC).…”

Section: Introductionmentioning

confidence: 99%

Exploring Photovoltaic Feasibility of Pentaaryl [60]Fullerene in Bulk Heterojunction Architecture

Mikie¹,

Saeki²,

Ikuma³

et al. 2014

J. Photopol. Sci. Technol.

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The photochemical process of pentaaryl [60]fullerenes (PAC 60 ) has been investigated by fluorescence and transient absorption spectroscopies, aiming at their use in bulk heterojunction organic photovoltaic (OPV). Fluorescence quenching was observed by adding C 60 into PAC 60 , where the intensity was decreased in an exponential manner. The photo-generated radical cation of PAC 60 was identified at 925 nm in the presence of electron acceptor. Motivated from the observed shallow molecular orbital levels of PAC 60 , we performed conceptual study of all-fullerene OPV, where PAC 60 and [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM) were presumably used as a p-type and n-type semiconductor, respectively. The power conversion efficiency was 0.007%, much smaller than 0.05% found for the conventional combination of P3HT (p-type) and PAC 60 (n-type). The mechanism is discussed on the basis of photoconductive and spectroscopic results.

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The First Pentahaptofullerene Metal Complexes

Cited by 284 publications

References 8 publications

Chemistry of η5-fullerene metal complexes

Chemistry of η5-fullerene metal complexes

Organometallic chemistry of extended periodic π-electron systems: hexahapto-chromium complexes of graphene and single-walled carbon nanotubes

Exploring Photovoltaic Feasibility of Pentaaryl [60]Fullerene in Bulk Heterojunction Architecture

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