Preparation and Characterization of Disilylbenzene and Bis(trimethoxysilyl)-benzene<sup>1</sup>

Bilow, N.; Brady, Jeffrey; Segal, C. L.

doi:10.1021/jo01062a070

Cited by 3 publications

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“…Toluene, benzene, and silane were "electronic" grade and were used as received. Disilylbenzene was prepared from bis-(trichlorosilyl)-benzene (obtained from Chemical Procurement Laboratories, Incorporated and purified by fractionation) by LiA1H4 reduction (13). The proton NMR spectrum (CC14 solution) of the 57~176 fraction (25 Torr) showed a sharp SiI-Ia singlet at 5 4.19 (integral 80) and at least 7 lines between ~ 7.13-7.77 (integral 53) indicating a mixture C6H4 (SiHs)~ isomers.…”

Section: Methodsmentioning

confidence: 99%

Polymerization of Aromatic Silanes in RF Plasmas

Haller

1982

J. Electrochem. Soc.

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Phenylsilane, r subjected to a low power rf discharge at low pressures and elevated temperatures results in polymeric films of unusual properties. In contrast to the known plasma chemistry of other aromatic materials, the benzene ring of #Sill3 does not fragment in the plasma polymerization process as is indicated by the virtual absence of aliphatic C-H stretching frequencies in the infrared spectrum of the deposited film. A similar lack of aliphatic hydrogen is observed in plasma polymers from diphenylsilane, disilylbenzene, and p-chlorophenylsilane. The predominant structural features of the phenylsilane plasma polymer films are cross-linked polysilane chains with pendant phenyl groups. The degree of cross-linking increases with increasing substrate temperature. The films are resistant to thermal degradation in vacuo to 500~ and maintain their mechanical integrity during thermal oxidation in air.The formation of polymeric films in radio frequency glow discharges have been reported (1, 2) for numerous saturated and unsaturated organic compounds. A common characteristic of these films is that their composition shows little resemblance to the monomeric starting material. In particular, it is well known that the benzene rings of aromatic starting materials suffer extensive fragmentation in the plasma, even under relatively mild discharge conditions, and the resulting polymers contain a large fraction of the total hydrogen in aliphatic C-H bonds (2-5). The main purpose of this paper is to report that plasma polymers formed from aromatic silanes are virtually free from aliphatic hydrogen, which indicates a protective effect in rf plasmas of silyl substituents on aromatic rings.A polymeric silicon hydride (the so-called "hydrogenated amorphous silicon") prepared by subjecting Sill4 to an rf glow discharge, is a useful semiconductor electronically dopable with conventional dopants for crystalline silicon (6-9). Another purpose of this paper is to address the question whether analogous semiconductors can be obtained by replacement of hydrogen with phenyl substituents.Thin films of silicon oxides and nitrides have extensively been used as protective layers in the processing of crystalline silicon based integrated circuits (10, 11). Silicon carbide fibers of high tensile strength have reportedly (12) been prepared from polydimethyl silanes. A third purpose of this paper is to report that analogous useful films can be prepared by simple thermal treatment of phenylsilane plasma polymer films. ExperimentalMaterials.~Phenylsilane, diphenylsilane, and p-chlorophenylsilane were obtained from Petrarch Systems, Incorporated, and were purified by distillation [bp 120 ~ (at 760 Torr), 132 ~ (16), and 72~ ~ (56), resp.]. Toluene, benzene, and silane were "electronic" grade and were used as received. Disilylbenzene was prepared from bis-(trichlorosilyl)-benzene (obtained from Chemical Procurement Laboratories, Incorporated and purified by fractionation) by LiA1H4 reduction (13). The proton NMR spectrum (CC14 solution) of the 57~176 f...

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Section: Methodsmentioning

confidence: 99%

Polymerization of Aromatic Silanes in RF Plasmas

Haller

1982

J. Electrochem. Soc.

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Pyrolysis of methylphenyldichlorosilane

Андрианов¹,

Kotov²,

Kovalenko³

1972

Russ Chem Bull

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The Wurtz−Fittig Reaction in the Preparation of C-Silylated Calixarenes

2007

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The Wurtz-Fittig reaction of tetraiodo calixarene 3 with Na/Me3SiCl in DME gave a mixture of tetrakis- and tris-silylated calixarenes (6 and 7). Tris(silyl) calixarene 7 was assigned the flattened cone conformation. A model study using p-bromoanisole and p-iodoanisole with Na/Me3SiCl gave the best results with p-bromoanisole in toluene. Attempts to extend this reaction to the tetrabromo calixarene 4 resulted in slow reactions giving mixtures of products. However, the Wurtz-Fittig reaction of the bromo benzyloxycalixarene 5 was faster, giving the debenzylated silyl ether 12.

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Preparation and Characterization of Disilylbenzene and Bis(trimethoxysilyl)-benzene¹

Cited by 3 publications

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Polymerization of Aromatic Silanes in RF Plasmas

Polymerization of Aromatic Silanes in RF Plasmas

Pyrolysis of methylphenyldichlorosilane

The Wurtz−Fittig Reaction in the Preparation of C-Silylated Calixarenes

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Preparation and Characterization of Disilylbenzene and Bis(trimethoxysilyl)-benzene1

Cited by 3 publications

References 0 publications

Polymerization of Aromatic Silanes in RF Plasmas

Polymerization of Aromatic Silanes in RF Plasmas

Pyrolysis of methylphenyldichlorosilane

The Wurtz−Fittig Reaction in the Preparation of C-Silylated Calixarenes

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Preparation and Characterization of Disilylbenzene and Bis(trimethoxysilyl)-benzene¹