22 Fullerenes

Calixarenes and fullerenes have novel properties that make them ideal materials for nanoscale electronic devices. [1][2][3][4] If fullerenes can be placed within a calixarene to form an ordered array, it could be possible to operate them and fabricate nanoscale circuits. As an essential prerequisite, the configurations of calixarenes and fullerenes included within calixarene units at a solid surface must be understood to construct the nanoscalar architecture. Calixarenes have a highly flexible molecular conformation, which is important in various chemical reactions and host-guest chemistry. [5,6] To understand the variety of molecular conformations that exist, resolution at the atomic or submolecular level is important, and is a challenging research activity in calixarene studies.Herein, we report the results of the construction and investigation of a calix[8]arene derivative, OBOCMC8 (C 104 H 128 O 24 ), [7] and the inclusion of C 60 in OBOCMC8 (C 60 / OBOCMC8). Scheme 1 a illustrates the chemical insertion of the buckyball into the calix structure, [8,9] and the structures of the calixarene and the inclusion complex are shown in Scheme 1 b and c, respectively. Well-ordered arrays of OBOCMC8 and C 60 /OBOCMC8 can be constructed on a Au(111) surface, and are clearly observed by scanning tunneling microscopy (STM). The results directly demonstrate a stable conformation of OBOCMC8 and the possibility of C 60 inclusion.The electrochemical behavior of the Au(111) surface in a solution containing OBOCMC8 and C 60 /OBOCMC8 was investigated by cyclic voltammetry. Cyclic voltammograms (CVs) were recorded in 0.1m HClO 4 using the so-called hanging meniscus method. After recording the standard CV of a bare Au(111) surface, a small amount of OBOCMC8 solution was added into the electrochemical cell. As a result, the oxidation peak, which is found at þ1.3 V for Au (111) [*] Prof.

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Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface

et al. 2003

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“…Recently, we 6,7 and others 8 reported an unusual reaction of electron-deficient acetylenes and triarylphosphines (or phosphites) with C 60 to give methanofullerenes 1 bearing an α-ylidic ester. Subsequent conversion of the ylide group in the presence of acids offered a unique approach to fullerene derivatives with phosphonium salt, phosphine oxide, phosphonate ester, and phosphinic acid moieties. , The unusual structure of methanofullerene ylides 1 prompts us to explore further the chemical properties of this class of compounds. Herein, we report a novel acid-catalyzed ring expansion of methanofullerene ylides 1 and 2 to cyclopentanofullerene and to cyclopentenofullerene derivatives.…”

Section: Introductionmentioning

confidence: 99%

Novel Acid-Catalyzed Rearrangement of Methanofullerenes Bearing an α-Ylidic Ester to Cyclopentanofullerenes: A Vinyl Cyclopropane-Type Ring Expansion

et al. 2003

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A novel acid-catalyzed ring expansion of methanofullerenes bearing an alpha-ylidic ester has been investigated. Treatment of dialkyl acetylenedicarboxylate and tricycloalkylphosphine with C(60) led to the isolation of a methanofullerene ylide after passing the reaction mixtures through a basic alumina column. If the reaction mixture was passed through a silica gel column, a cyclopentanofullerene was isolated instead. These new cyclopentanofullerenes consisted of a fused cyclopentanone ring bearing an alpha-hydroxy ester and a phosphonium ylide and were confirmed by their NMR, mass, and X-ray diffraction data. The cyclopentanofullerenes were formed by the ring expansion of the corresponding methanofullerenes in the presence of silica gel. The ring expansion also proceeded by treating methanofullerene with acetic acid in chloroform. On the other hand, the methanofullerenes from RO(2)CCCCO(2)R, PAr(3), and C(60) were stable in silica gel. However, upon heating with acetic acid at 50 degrees C, they underwent ring expansion and dephosphination to give cyclopentenofullerenes. An implicit vinyl cyclopropane ring expansion mechanism was proposed to account for this novel acid-catalyzed rearrangement.

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“…This review follows on from last year's report 1 and is a collection of the highlights from over 1500 research papers, reviews and books revealed by Web of Science and Chemical Abstracts searches for fullerene (and related nanotube) references. Furthermore, it is intended that the papers reviewed reflect the current research trends in the field.…”

Section: Introductionmentioning

confidence: 99%

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Birkett

2001

Annu. Rep. Prog. Chem., Sect. A

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22 Fullerenes

Cited by 7 publications

References 224 publications

Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface

Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface

Novel Acid-Catalyzed Rearrangement of Methanofullerenes Bearing an α-Ylidic Ester to Cyclopentanofullerenes: A Vinyl Cyclopropane-Type Ring Expansion

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22 Fullerenes

Cited by 7 publications

References 224 publications

Configurations of a Calix[8]arene and a C60/Calix[8]arene Complex on a Au(111) Surface

Configurations of a Calix[8]arene and a C60/Calix[8]arene Complex on a Au(111) Surface

Novel Acid-Catalyzed Rearrangement of Methanofullerenes Bearing an α-Ylidic Ester to Cyclopentanofullerenes: A Vinyl Cyclopropane-Type Ring Expansion

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Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface

Configurations of a Calix[8]arene and a C₆₀/Calix[8]arene Complex on a Au(111) Surface