Synthesis of the Higher-Order Diamondoid Hexamantane Using Low-Temperature Plasmas Generated in Supercritical Xenon

Stauss, Sven; Miyazoe, Hiroyuki; Shizuno, Tomoki; Saito, Koya; Sasaki, Takehiko; Terashima, Kazuo

doi:10.1143/jjap.49.070213

Cited by 18 publications

(20 citation statements)

References 22 publications

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“…25 The highest yield of diamantane of ca. [28][29][30][31] However, the yields were very low. 26 Similar attempts were made to prepare higher diamondoids via carbocation rearrangement of the corresponding cyclic hydrocarbons, and the highest diamondoid synthesized was anti-tetramantane (C 22 H 28 ).…”

Section: Preparation Of Diamondoidsmentioning

confidence: 99%

Derivatization of diamondoids for functional applications

et al. 2015

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Diamondoids, a group of hydrocarbon cage molecules that resemble diamond lattice, are attracting increasing interest in the past decade. Their diamond-like structure warrants that diamondoids inherit the superior properties of diamond at nanoscale, including exceptional hardness and stiffness, high thermal stability, high chemical resistance, unique optical properties and fluorescence, and excellent biocompatibility. To effectively take advantage of the fascinating properties of diamondoids, they must be properly functionalized so that they can be covalently incorporated into the host systems or compatibly mixed with the hosts. Herein, the origin, synthesis, derivatization, and application of diamondoids are reviewed. In particular, how the derivatized diamondoids for various functional applications, including pharmaceuticals, polymers, fine chemicals, nanomaterials, and optical devices, are discussed. It is hoped that this review article can attract more interest in diamondoids, which in turn helps motivate the development of new synthesis and application of diamondoids and their derivatives so that this group of unique molecules can bring more benefits. Scheme 3 Bromination of adamantane under phase-transfer conditions.Scheme 4 Synthesis of 1,3,5,7-tetrabromoadamantane.Scheme 5 Preparation of 1-adamantanol by the ozonation of adamantane over silica gel.Scheme 6 Preparation of adamantyl amine.Scheme 7 Preparation of 1,3-adamantanedicarboxylic acid.

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Section: Preparation Of Diamondoidsmentioning

confidence: 99%

Derivatization of diamondoids for functional applications

et al. 2015

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“…The experimental setup and procedure used for generating the DBD plasmas in scXe using arrayed microelectrodes has already been reported in detail before [21,22]. The electrodes and the diamond precursor adamantane (molecular mass ∼ 136 g mol −1 ) were placed in a custom-made high-pressure cell.…”

Section: Experimental Approachmentioning

confidence: 99%

“…This also shows that larger amounts of precursors can help to increase the quantity of the synthesized product. However, it was observed that for much larger amounts of adamantane (on the order of ∼ 50 − 100 mg), it became more difficult to ignite the plasma [21,22], therefore the amount of precursor cannot be increased to arbitrarily high values. In Fig.…”

Section: Variation Of Reaction Yieldsmentioning

confidence: 99%

“…Recently, it has been demonstrated that nanodiamonds [20] and diamondoids can be synthesized both by dielectric barrier discharges (DBDs) [21][22][23] and pulsed laser ablation plasmas in supercritical xenon (scXe) [24] and CO 2 [25]. In these reports, the diamondoids were characterized by energy-dispersive X-ray spectroscopy, micro-Raman spectroscopy, and gas chromatography -mass spectrometry (GC-MS).…”

Section: Introductionmentioning

confidence: 99%

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Reaction yields of diamondoid synthesis by plasmas generated in supercritical xenon

Stauss

Shizuno

Miyazoe

et al. 2013

Trans. Mat. Res. Soc. Japan

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Diamondoids are sp3 -hybridized carbon nanomaterials that hold promise for application in biotechnology, medicine, and opto-and nanoelectronics. While difficult or even impossible to realize by conventional organic synthesis methods, the synthesis of larger diamondoids was demonstrated by plasmas generated in supercritical fluids, however, the reaction mechanisms that lead to their formation are not clear. Here, we investigated the synthesis of diamondoids from adamantane and present a simple model that predicts the reaction rates of diamantane, triamantane, and tetramantane. The diamondoids were synthesized by micro dielectric barrier discharges arranged in arrays, generated at frequencies of 7 kHz and applied voltages of 5 − 10 kV p−p in supercritical xenon (pressure 5.56 − 8.22 MPa, temperature 290.0 − 310.2 K). The collected samples were analyzed and quantified by gas chromatography -mass spectrometry measurements. The reaction yields of diamantane increase with increasing precursor density and longer reaction times. Experimental data also suggests a stepwise reaction of higher diamondoids from lower diamondoids, and predicts lower reaction rates for higher diamondoids when compared to lower diamondoids.

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“…In the early 2000's, Shibuya et al (2002) represented two convenient methods for synthesis of enantiomeric adamantane derivatives. Recently a short report on the synthesis of hexamantane is reported using low-temperature plasmas generated in supercritical xenon with limited success (Stauss et al, 2010). Otherwise, high molecular weight diamondoids have not been synthesized as of this date.…”

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confidence: 99%

Diamondoid Molecules

Mansoori

Araújo

2011

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Diamondoid molecules are cage-like, ultra stable and saturated hydrocarbons. The basic repetitive unit of the diamondoids is a ten-carbon tetracyclic cage system called "adamantane" (Fig. 1.1). They are called "diamondoid" because they have at least one adamantane unit and their carbon-carbon framework is completely or largely superimposable on the diamond lattice (Balaban and Schleyer, 1978; Mansoori, 2007). The diamond lattices structure was first determined in 1913 by Bragg and Bragg using X-ray diffraction analysis (Bragg and Brag, 1913). Diamondoids show unique properties due to their exceptional atomic arrangements. Adamantane consists of cyclohexane rings in "chair" conformation. The name adamantane is derived from the Greek language word for diamond since its chemical structure is like the three-dimensional diamond subunit as it is shown in Fig. 1.2. 1.2. Classification and Crystalline Structure of Diamondoids The first and simplest member of the diamondoids group, adamantane, is a tricyclic saturated hydrocarbon (tricyclo[3.3.1.1(3.7)]decane, according to the von Bayer systematic nomenclature).

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Synthesis of the Higher-Order Diamondoid Hexamantane Using Low-Temperature Plasmas Generated in Supercritical Xenon

Cited by 18 publications

References 22 publications

Derivatization of diamondoids for functional applications

Derivatization of diamondoids for functional applications

Reaction yields of diamondoid synthesis by plasmas generated in supercritical xenon

Diamondoid Molecules

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