JPH05230219A - Production of alpha,omega-dihydropolysilane - Google Patents
Production of alpha,omega-dihydropolysilaneInfo
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- JPH05230219A JPH05230219A JP6974992A JP6974992A JPH05230219A JP H05230219 A JPH05230219 A JP H05230219A JP 6974992 A JP6974992 A JP 6974992A JP 6974992 A JP6974992 A JP 6974992A JP H05230219 A JPH05230219 A JP H05230219A
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- ring
- polysilane
- solvent
- group
- formula
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は下記一般式［Ｉ］The present invention relates to the following general formula [I]
【化３】 （式中Ｒ1，Ｒ2，Ｒ3，Ｒ4，Ｒ5，Ｒ6，Ｒ7およびＲ8は
各々独立に水素原子、アルキル基、アリール基、アルケ
ニル基、アルキニル基、アルコキシル基、シリル基また
はハロゲン原子を表す。Ｒ1とＲ2，Ｒ3とＲ4，Ｒ5とＲ6
またはＲ7とＲ8は結合しているケイ素と一体となって環
を形成しうる。ｍは０または１を表す。ｎは２以上の整
数を表す。）で表されるα，ω−ジヒドロポリシラン類
の製造方法に関する。[Chemical 3] (In the formula, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alkoxyl group, a silyl group. Or a halogen atom, R 1 and R 2 , R 3 and R 4 , R 5 and R 6
Alternatively, R 7 and R 8 may together with the silicon to which they are attached form a ring. m represents 0 or 1. n represents an integer of 2 or more. ) And a method for producing α, ω-dihydropolysilanes.
【０００２】本発明で得られるα，ω−ジヒドロポリシ
ラン類はさらに高分子量のポリシラン類の合成中間体と
して有用である［ＵＳ Ｐａｔ．ＵＳ５００３１０
０］。また本発明によれば、非線形光学材料や導伝性高
分子などの機能性高分子として有用なポリシラン類を種
々合成できる［”有機ケイ素ポリマーの合成と応用”シ
ーエムシー（１９８９）；化学技術研究所報告、８、５
６９（１９８９）］。The α, ω-dihydropolysilanes obtained by the present invention are useful as synthetic intermediates for higher molecular weight polysilanes [US Pat. US500310
0]. Further, according to the present invention, various polysilanes useful as functional polymers such as nonlinear optical materials and conductive polymers can be synthesized [[Synthesis and application of organosilicon polymer] CMC (1989); Chemical Technology Research) Report, 8 , 5
69 (1989)].
【０００３】[0003]
【従来の技術】一般式［Ｉ］で表されるポリシラン類の
合成法としては、（１）ジクロロシラン類をナトリウム
などアルカリ金属存在下、還元縮合する方法［”有機ケ
イ素ポリマーの合成と応用”シーエムシー（１９８９）
ｐ９９］。2. Description of the Related Art As a synthesis method of polysilanes represented by the general formula [I], (1) dichlorosilanes are reduced and condensed in the presence of an alkali metal such as sodium ["Synthesis and application of organosilicon polymer"]. CMC (1989)
p99].
【０００４】（２）遷移金属触媒存在下、ポリヒドロシ
ラン類を脱水素縮合する方法［Ｃａｎ．Ｊ．Ｃｈｅ
ｍ．，６５，１８０４（１９８７）；Ｊ．Ｏｒｇａｎｏ
ｍｅｔ．Ｃｈｅｍ．，２７，Ｃ３１（１９７１）］。(2) Method for dehydrogenative condensation of polyhydrosilanes in the presence of a transition metal catalyst [Can. J. Che
m. , 6 5,1804 (1987); J . Organo
met. Chem. , 2 7, C31 (1971) ].
【０００５】（３）ジシレンの等価体であるジシラビシ
クロオクタジエンのアニオン重合による方法［Ｊ．Ａ
ｍ．Ｃｈｅｍ．Ｓｏｃ．，１１１，７６４１（１９８
９）］。(3) Method by anionic polymerization of disilabicyclooctadiene which is an equivalent of disilene [J. A
m. Chem. Soc. , 11 11,7641 (198
9)].
【０００６】（４）ジクロロシラン類の電解還元による
方法［Ｊ．Ｃｈｅｍ．Ｓｏｃ．，Ｃｈｅｍ．Ｃｏｍｍｕ
ｎ．，１１６０（１９９０）］。(4) Method by electrolytic reduction of dichlorosilanes [J. Chem. Soc. Chem. Commu
n. , 1160 (1990)].
【０００７】（５）シクロテトラシラン類と触媒量のブ
チルリチウムを反応させる方法［Ｊ．Ａｍ．Ｃｈｅｍ．
Ｓｏｃ．，１１３，１０４６（１９９１）］などがあ
る。(5) Method of reacting cyclotetrasilane with a catalytic amount of butyllithium [J. Am. Chem.
Soc. , 1 13, 1046 (1991)].
【０００８】これらの方法のうち（１）および（４）の
方法では側鎖に導入できる官能基が限られるうえ、分子
量分布が一様でないなどの欠点がある。Among these methods, the methods (1) and (4) have the drawbacks that the functional groups that can be introduced into the side chain are limited and the molecular weight distribution is not uniform.
【０００９】（２）の方法では用いることができる基質
がモノ置換シランに限られるうえ、分子量分布が一様で
ないなどの欠点をもつ。In the method (2), the substrates that can be used are limited to mono-substituted silanes, and the molecular weight distribution is not uniform.
【００１０】（３）の方法では反応開始剤として活性な
アルキルリチウムを用いるため、側鎖に導入できる官能
基が限られているという欠点がある。In the method (3), since active alkyllithium is used as a reaction initiator, there is a drawback that the functional groups that can be introduced into the side chain are limited.
【００１１】（５）の方法では用いることができる基質
が著しく限定される。In the method (5), the substrates that can be used are extremely limited.
【００１２】[0012]
【発明が解決しようとする課題】本発明者らは工業化の
可能かつ高選択的なポリシラン合成法につき検討を加え
た結果、重合触媒存在下、オクタエチルシランをはじめ
とする小員環ポリシラン類を開環重合させることによ
り、前記一般式［Ｉ］で表されるα，ω−ジヒドロポリ
シラン類が得られることを見いだし本発明を完成した。DISCLOSURE OF THE INVENTION The present inventors have conducted studies on a highly selective and highly selective polysilane synthesis method which can be industrialized, and as a result, in the presence of a polymerization catalyst, small ring polysilanes such as octaethylsilane have been produced. The present invention has been completed by finding that α, ω-dihydropolysilanes represented by the above general formula [I] can be obtained by ring-opening polymerization.
【００１３】[0013]
【課題を解決するための手段】本発明は重合触媒存在
下、下記一般式［ＩＩ］The present invention provides the following general formula [II] in the presence of a polymerization catalyst.
【００１４】[0014]
【化４】 （式中、Ｒ1，Ｒ2，Ｒ3，Ｒ4，Ｒ5，Ｒ6，Ｒ7，Ｒ8 お
よびｍは前記と同様の意味を表す。）で表される小員環
ポリシランを開環重合させることにより、前記一般式
［Ｉ］で表されるα，ω−ジヒドロポリシラン類を製造
する方法である。[Chemical 4] (Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and m have the same meanings as described above). It is a method for producing α, ω-dihydropolysilanes represented by the general formula [I] by polymerizing.
【００１５】本発明に用いる前記一般式［ＩＩ］で表さ
れる小員環ポリシランはリチウムまたはナトリウムによ
りジクロロシラン類を縮合させる方法［Ｊ．Ｃｈｅｍ．
Ｓｏｃ．，Ｃｈｅｍ．Ｃｏｍｍｕｎ．，７８１（１９８
３）；Ｏｒｇａｎｏｍｅｔａｌｌｉｃｓ，３，１４１
（１９８４）；Ｃｈｅｍ．Ｌｅｔｔ．，１７１１（１９
８３）；Ｊ．Ｏｒｇａｎｏｍｅｔ．Ｃｈｅｍ．，２１
２，１５５（１９８１）；Ｐｏｌｙｍ．Ｐｒｅｐｒ．３
１，４６（１９９０）；Ｏｒｇａｎｏｍｅｔａｌｌｉｃ
ｓ，２，１７７１（１９８３）］により容易に得られ
る。The small-ring polysilane represented by the above general formula [II] used in the present invention is prepared by condensing dichlorosilanes with lithium or sodium [J. Chem.
Soc. Chem. Commun. , 781 (198
3); Organometallics, 3 , 141
(1984); Chem. Lett. , 1711 (19
83); Organomet. Chem. , 2 1
2, 155 (1981); Polym. Prepr. Three
1,46 (1990); Organometallic
s, 2 , 1771 (1983)].
【００１６】前記一般式［ＩＩ］で表される小員環ポリ
シランとしてはたとえば、ヘキサプロピルシクロトリシ
ラン、ヘキサ（２，２−ジメチルプロピル）シクロトリ
シラン、ヘキサ（１，１−ジメチルエチル）シクロトリ
シラン、ヘキサメシチルシクロトリシラン、オクタ（ト
リメチルシリル）シクロテトラシラン、オクタエチルシ
クロテトラシラン、オクタ（イソプロピル）シクロテト
ラシラン、オクタフェニルシクロテトラシラン、１，
２，３，４−テトラメチル−１，２，３，４−テトラフ
ェニルシラン、１，２，３，４−テトラブロモー１，
２，３，４−テトラフェニルシクロテトラシラン、１，
２，３，４−テトラメトキシ−１、２、３、４−テトラ
フェニルシクロテトラシラン、１，２，３，４−テトラ
フェニルシクロテトラシラン、１，２，３，４−テトラ
ビニル−１，２，３，４−テトラエチルシクロテトラシ
ラン、１，２，３，４−テトラエチニル−１，２，３，
４−テトラフェニルシクロテトラシランなどをあげるこ
とができる。Examples of the small-ring polysilane represented by the general formula [II] include hexapropylcyclotrisilane, hexa (2,2-dimethylpropyl) cyclotrisilane, and hexa (1,1-dimethylethyl) cyclo. Trisilane, hexamesitylcyclotrisilane, octa (trimethylsilyl) cyclotetrasilane, octaethylcyclotetrasilane, octa (isopropyl) cyclotetrasilane, octaphenylcyclotetrasilane, 1,
2,3,4-tetramethyl-1,2,3,4-tetraphenylsilane, 1,2,3,4-tetrabromo-1,
2,3,4-tetraphenylcyclotetrasilane, 1,
2,3,4-tetramethoxy-1,2,3,4-tetraphenylcyclotetrasilane, 1,2,3,4-tetraphenylcyclotetrasilane, 1,2,3,4-tetravinyl-1, 2,3,4-tetraethylcyclotetrasilane, 1,2,3,4-tetraethynyl-1,2,3
4-tetraphenylcyclotetrasilane etc. can be mentioned.
【００１７】本発明は重合触媒共存下で反応を行うこと
が必須の条件である。重合触媒としては、ヨードトリメ
チルシラン、ヨードトリエチルシラン、トリフルオロメ
タンスルホン酸トリメチルシリル、トリフルオロメタン
スルホン酸トリエチルシリル、シアン化トリメチルシリ
ル、ブロモトリメチルシラン、過塩素酸トリメチルシリ
ル、ヨウ素、シュウ素、トリフルオロメタンスルホン
酸、四塩化チタン、四塩化スズ、トリフルオロボランジ
エチルエーテル錯体などのルイス酸を用いることができ
る。また、アゾビス（イソブチロニトリル）、トリエチ
ルボラン等のラジカル開始剤を単独またはトリブチルス
ズヒドリド、ジフェニルメチルシラン、トリス（トリメ
チルシリル）シランなどと組み合わせて、用いることが
できる。また、フッ化テトラブチルアンモニウム、トリ
ス（ジエチルアミノ）スルホニウムジフルオロトリメチ
ルシリカート等の求核反応剤も用いることができる。使
用量はいわゆる触媒量でよい。In the present invention, it is an essential condition to carry out the reaction in the presence of a polymerization catalyst. As the polymerization catalyst, iodotrimethylsilane, iodotriethylsilane, trimethylsilyl trifluoromethanesulfonate, triethylsilyl trifluoromethanesulfonate, trimethylsilyl cyanide, bromotrimethylsilane, trimethylsilyl perchlorate, iodine, arsenic, trifluoromethanesulfonic acid, four Lewis acids such as titanium chloride, tin tetrachloride, and trifluoroborane diethyl ether complex can be used. Further, radical initiators such as azobis (isobutyronitrile) and triethylborane can be used alone or in combination with tributyltin hydride, diphenylmethylsilane, tris (trimethylsilyl) silane and the like. Further, a nucleophilic reaction agent such as tetrabutylammonium fluoride or tris (diethylamino) sulfonium difluorotrimethylsilicate can be used. The amount used may be a so-called catalytic amount.
【００１８】本発明は溶媒を用いるものであり、溶媒と
してはジクロロメタン、１，２−ジクロロエタン、１，
１，１−トリクロロエタン、クロロベンゼン、ジクロロ
ベンゼン、クロロホルム等のハロゲン化炭化水素を単独
または混合して用いることができる。さらに、これらの
溶媒をハロゲン化炭化水素溶媒以外の溶媒と混合して用
いることもできる。反応は−７８−２００℃の範囲で行
うことができるが反応の効率の点で室温から１００℃で
行うことが望ましい。また収率を向上させる上で超音波
照射下で反応を行うことが望ましい。The present invention uses a solvent, and as the solvent, dichloromethane, 1,2-dichloroethane, 1,
Halogenated hydrocarbons such as 1,1-trichloroethane, chlorobenzene, dichlorobenzene and chloroform can be used alone or in combination. Further, these solvents may be mixed with a solvent other than the halogenated hydrocarbon solvent and used. The reaction can be carried out in the range of −78 to 200 ° C., but it is desirable to carry out the reaction at room temperature to 100 ° C. in view of reaction efficiency. Further, it is desirable to carry out the reaction under ultrasonic irradiation in order to improve the yield.
【００１９】以下実施例により本発明をさらに詳しく説
明する。The present invention will be described in more detail with reference to the following examples.
【００２０】[0020]
実施例１ Example 1
【００２１】[0021]
【化５】 [Chemical 5]
【００２２】アルゴン雰囲気下、液体窒素を用いて凍結
−脱気した１，２−ジクロロエタン（１ｍｌ）にオクタ
エチルシクロテトラシラン１０３ｍｇ（０．０３０ｍｍ
ｏｌ）を加え、さらに凍結−脱気を三回繰り返した。ヨ
ードトリメチルシランの１，２−ジクロロエタン溶液
（１．０Ｍ）を３０μｌ（０．０３０ｍｍｏｌ）加え、
反応容器を溶封した後、室温下、超音波照射を１０時間
行った。反応容器を液体窒素で凍結し、溶封部をアルゴ
ン雰囲気下で開口し、反応容器を室温に戻した後、減圧
下、溶媒を留去した。ヘキサン（２ｍｌ）および飽和重
曹水（２ｍｌ）を加え、かくはんした後、ヘキサン層を
分離し、硫酸マグネシウムで乾燥した。得られた粗生成
物をシリカゲルカラム（ＥｔＯＡｃ：Ｈｅｘａｎｅ＝
１：２０）により精製し変換率４６％で１，１，２，
２，３，３，４，４，５，５，６，６，７，７，８，８
−ヘキサデカエチルオクタシラン（選択率５３％）およ
び１，１，２，２，３，３，４，４，５，５，６，６，
７，７，８，８，９，９，１０，１０，１１，１１，１
２，１２−テトラコサエチルドデカシラン（選択率４７
％）を得た。103 mg (0.030 mm) of octaethylcyclotetrasilane was added to 1,2-dichloroethane (1 ml) which had been freeze-degassed with liquid nitrogen under an argon atmosphere.
ol) was added, and freeze-deaeration was repeated three times. 30 μl (0.030 mmol) of 1,2-dichloroethane solution (1.0 M) of iodotrimethylsilane was added,
After the reaction vessel was sealed, ultrasonic irradiation was performed at room temperature for 10 hours. The reaction vessel was frozen with liquid nitrogen, the sealed portion was opened under an argon atmosphere, the reaction vessel was returned to room temperature, and then the solvent was distilled off under reduced pressure. Hexane (2 ml) and saturated aqueous sodium hydrogen carbonate (2 ml) were added, the mixture was stirred, and then the hexane layer was separated and dried over magnesium sulfate. The resulting crude product was applied to a silica gel column (EtOAc: Hexane =
1:20) to convert 1,1,2,
2,3,3,4,4,5,5,6,6,7,7,8,8
-Hexadecaethyloctasilane (selectivity 53%) and 1,1,2,2,3,3,4,4,5,5,6,6,6
7,7,8,8,9,9,10,10,11,11,1
2,12-Tetracosaethyldodecasilane (selectivity 47
%) Was obtained.
【００２３】１，１，２，２，３，３，４，４，５，
５，６，６，７，７，８，８−ヘキサデカエチルオクタ
シラン1 Ｈ ＮＭＲ（ＣＤＣｌ3）：δ０．３０−１．６０
（ｍ，８０Ｈ），３．６３（ｑｕｉｎｔｅｔ，Ｊ＝３．
２Ｈｚ，２Ｈ）1, 1, 2, 2, 3, 3, 4, 4, 5,
5,6,6,7,7,8,8-Hexadecaethyloctasilane 1 H NMR (CDCl 3 ): δ 0.30 to 1.60
(M, 80H), 3.63 (quintet, J = 3.
2Hz, 2H)
【００２４】ＩＲ（ｎｅａｔ）：２９８０，２０７０，
１４６０，１００５，７９０，７００ｃｍ-1 Ａｎａｌ． Ｃａｌｃｄ．ｆｏｒ Ｃ32Ｈ82Ｓｉ8：Ｃ，５５．５
７；Ｈ，１１．９５ Ｆｏｕｎｄ：Ｃ，５５．５８；Ｈ，１２．０３IR (neat): 2980, 2070,
1460, 1005, 790, 700 cm -1 Anal. Calcd. for C 32 H 82 Si 8 : C, 55.5
7; H, 11.95 Found: C, 55.58; H, 12.03.
【００２５】１，１，２，２，３，３，４，４，５，
５，６，６，７，７，８，８，９，９，１０，１０，１
１，１１，１２，１２−テトラコサエチルドデカシラン1 Ｈ ＮＭＲ（ＣＤＣｌ3）：δ０．３０−１．６０
（ｍ，１２０Ｈ），３．７０（ｑｕｉｎｔｅｔ，Ｊ＝
３．２Ｈｚ，２Ｈ）1, 1, 2, 2, 3, 3, 4, 4, 5,
5,6,6,7,7,8,8,9,9,10,10,1
1,11,12,12-Tetracosaethyldodecasilane 1 H NMR (CDCl 3 ): δ 0.30 to 1.60
(M, 120H), 3.70 (quintet, J =
3.2Hz, 2H)
【００２６】ＩＲ（ｎｅａｔ）：２９８０，２０７０，
１４６０，１００５，７９０，７００ｃｍ-1 IR (neat): 2980, 2070,
1460, 1005, 790, 700 cm -1
【００２７】Ａｎａｌ． Ｃａｌｃｄ．ｆｏｒ Ｃ48Ｈ122Ｓｉ12：Ｃ，５５．６
２；Ｈ，１１．８６ Ｆｏｕｎｄ：Ｃ，５５．５５；Ｈ，１２．１６Anal. Calcd. for C 48 H 122 Si 12 : C, 55.6
2; H, 11.86 Found: C, 55.55; H, 12.16
【００２８】実施例２Example 2
【００２９】[0029]
【化６】 [Chemical 6]
【００３０】実施例１同様な実験手順で溶媒として１，
２−ジクロロエタンのかわりにジクロロメタンを用いて
オクタエチルテトラシクロシラン１０３ｍｇ（０．３０
ｍｍｏｌ）と触媒量のヨードトリメチルシラン（０．０
３０ｍｍｏｌ）の反応を行い、変換率３４％で１，１，
２，２，３，３，４，４，５，５，６，６，７，７，
８，８−ヘキサデカエチルオクタシラン（選択率８０
％）および１，１，２，２，３，３，４，４，５，５，
６，６，７，７，８，８，９，９，１０，１０，１１，
１１，１２，１２−テトラコサエチルドデカシラン（選
択率２０％）を得た。生成物のスペクトルは実施例１で
得たものと一致した。Example 1 In the same experimental procedure as the solvent 1,
Dichloromethane was used instead of 2-dichloroethane to obtain 103 mg of octaethyltetracyclosilane (0.30
mmol) and a catalytic amount of iodotrimethylsilane (0.0
30 mmol) reaction to obtain 1,1, at a conversion rate of 34%.
2, 2, 3, 3, 4, 4, 5, 5, 6, 6, 6, 7, 7,
8,8-Hexadecaethyloctasilane (selectivity 80
%) And 1,1,2,2,3,3,4,4,5,5,5
6, 6, 7, 7, 8, 8, 9, 9, 10, 10, 11,
11,12,12-Tetracosaethyldodecasilane (selectivity 20%) was obtained. The product spectrum was consistent with that obtained in Example 1.
【００３１】実施例３Example 3
【００３２】[0032]
【化７】 [Chemical 7]
【００３３】実施例１同様な実験手順で溶媒として１，
２−ジクロロエタンのかわりにジクロロメタンを用いて
オクタエチルテトラシクロシラン１０３ｍｇ（０．３０
ｍｍｏｌ）と触媒量のトリフルオロメタンスルホン酸ト
リメチルシリル（０．０３０ｍｍｏｌ）の反応を行い、
変換率３３％で１，１，２，２，３，３，４，４，５，
５，６，６，７，７，８，８−ヘキサデカエチルオクタ
シラン（選択率１００％）を得た。生成物のスペクトル
は実施例１で得たものと一致した。Example 1 In the same experimental procedure as the solvent 1,
Dichloromethane was used instead of 2-dichloroethane to obtain 103 mg of octaethyltetracyclosilane (0.30
mmol) and a catalytic amount of trimethylsilyl trifluoromethanesulfonate (0.030 mmol) are reacted,
Conversion rate of 33%, 1,1,2,2,3,3,4,4,5
5,6,6,7,7,8,8-hexadecaethyloctasilane (selectivity 100%) was obtained. The product spectrum was consistent with that obtained in Example 1.
【００３４】実施例４Example 4
【００３５】[0035]
【化８】 [Chemical 8]
【００３６】実施例１同様な実験手順で溶媒として１，
２−ジクロロエタンのかわりにジクロロメタンを用いて
オクタエチルテトラシクロシラン１０３ｍｇ（０．３０
ｍｍｏｌ）と触媒量のヨウ素（０．０１５ｍｍｏｌ）の
反応を行い変換率４０％で１，１，２，２，３，３，
４，４，５，５，６，６，７，７，８，８−ヘキサデカ
エチルオクタシラン（選択率６９％）および１，１，
２，２，３，３，４，４，５，５，６，６，７，７，
８，８，９，９，１０，１０，１１，１１，１２，１２
−テトラコサエチルドデカシラン（選択率３１％）を得
た。生成物のスペクトルは実施例１で得たものと一致し
た。Example 1 In the same experimental procedure as the solvent 1,
Dichloromethane was used instead of 2-dichloroethane to obtain 103 mg of octaethyltetracyclosilane (0.30
mmol) and a catalytic amount of iodine (0.015 mmol) are reacted at a conversion of 40% to 1,1,2,2,3,3,3.
4,4,5,5,6,6,7,7,8,8-hexadecaethyloctasilane (selectivity 69%) and 1,1,
2, 2, 3, 3, 4, 4, 5, 5, 6, 6, 6, 7, 7,
8,8,9,9,10,10,11,11,12,12
-Tetracosaethyldodecasilane (selectivity 31%) was obtained. The product spectrum was consistent with that obtained in Example 1.
Claims (1)
において、開環重合させることからなる下記一般式 【化２】 で表されるα，ω−ジヒドロポリシラン類の製造方法
（式中Ｒ1，Ｒ2，Ｒ3，Ｒ4，Ｒ5，Ｒ6，Ｒ7およびＲ8は
各々独立に水素原子、アルキル基、アリール基、アルケ
ニル基、アルキニル基、アルコキシル基、シリル基また
はハロゲン原子を表す。Ｒ1とＲ2，Ｒ3とＲ4，Ｒ5とＲ6
またはＲ7とＲ8は結合しているケイ素と一体となって環
を形成しうる。ｍは０または１を表す。ｎは２以上の整
数を表す）。1. The following general formula: A ring-opening polymerization of a small-ring polysilane represented by the following formula in a solvent in the presence of a polymerization catalyst: The method for producing α, ω-dihydropolysilanes represented by the formula (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently a hydrogen atom, an alkyl group, Represents an aryl group, an alkenyl group, an alkynyl group, an alkoxyl group, a silyl group or a halogen atom, R 1 and R 2 , R 3 and R 4 , R 5 and R 6
Alternatively, R 7 and R 8 may together with the silicon to which they are attached form a ring. m represents 0 or 1. n represents an integer of 2 or more).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6974992A JPH05230219A (en) | 1992-02-19 | 1992-02-19 | Production of alpha,omega-dihydropolysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6974992A JPH05230219A (en) | 1992-02-19 | 1992-02-19 | Production of alpha,omega-dihydropolysilane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05230219A true JPH05230219A (en) | 1993-09-07 |
Family
ID=13411764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6974992A Pending JPH05230219A (en) | 1992-02-19 | 1992-02-19 | Production of alpha,omega-dihydropolysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05230219A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0649219A (en) * | 1992-07-30 | 1994-02-22 | Shin Etsu Chem Co Ltd | Polysilane having hydrogen at both terminals and its production |
| EP1943669A2 (en) * | 2005-10-05 | 2008-07-16 | Nanogram Corporation | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| US7485691B1 (en) | 2004-10-08 | 2009-02-03 | Kovio, Inc | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8092867B2 (en) | 2006-10-06 | 2012-01-10 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
-
1992
- 1992-02-19 JP JP6974992A patent/JPH05230219A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0649219A (en) * | 1992-07-30 | 1994-02-22 | Shin Etsu Chem Co Ltd | Polysilane having hydrogen at both terminals and its production |
| US8236916B1 (en) | 2004-10-08 | 2012-08-07 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8455604B1 (en) | 2004-10-08 | 2013-06-04 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7485691B1 (en) | 2004-10-08 | 2009-02-03 | Kovio, Inc | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7491782B1 (en) | 2004-10-08 | 2009-02-17 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7723457B1 (en) | 2004-10-08 | 2010-05-25 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US7951892B1 (en) | 2004-10-08 | 2011-05-31 | Kovio, Inc. | Doped polysilanes, compositions containing the same, methods for making the same, and films formed therefrom |
| US8057865B1 (en) | 2004-10-08 | 2011-11-15 | Kovio, Inc. | Polysilane compositions, methods for their synthesis and films formed therefrom |
| US8242227B2 (en) | 2004-10-08 | 2012-08-14 | Kovio, Inc. | Doped polysilanes, compositions containing the same, methods for making the same, and films formed therefrom |
| US8378050B2 (en) | 2005-10-05 | 2013-02-19 | Kovio, Inc. | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| EP1943669A4 (en) * | 2005-10-05 | 2012-06-13 | Kovio Inc | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| US7943721B2 (en) | 2005-10-05 | 2011-05-17 | Kovio, Inc. | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| EP1943669A2 (en) * | 2005-10-05 | 2008-07-16 | Nanogram Corporation | Linear and cross-linked high molecular weight polysilanes, polygermanes, and copolymers thereof, compositions containing the same, and methods of making and using such compounds and compositions |
| US8092867B2 (en) | 2006-10-06 | 2012-01-10 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
| US8461284B2 (en) | 2006-10-06 | 2013-06-11 | Kovio, Inc. | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
| US8846507B2 (en) | 2006-10-06 | 2014-09-30 | Thin Film Electronics Asa | Silicon polymers, methods of polymerizing silicon compounds, and methods of forming thin films from such silicon polymers |
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