JP2002080840A - Light-emitting material and novel fullerene derivative - Google Patents
Light-emitting material and novel fullerene derivativeInfo
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- JP2002080840A JP2002080840A JP2000270030A JP2000270030A JP2002080840A JP 2002080840 A JP2002080840 A JP 2002080840A JP 2000270030 A JP2000270030 A JP 2000270030A JP 2000270030 A JP2000270030 A JP 2000270030A JP 2002080840 A JP2002080840 A JP 2002080840A
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、フラレーン誘導体
からなる発光材料及びアジリジン官能基を有する新規フ
ラーレン誘導体に関する。The present invention relates to a luminescent material comprising a fullerene derivative and a novel fullerene derivative having an aziridine functional group.
【０００２】[0002]
【従来の技術】フラーレンは大きなパイ電子共役系を有
しており、その特性を利用した発光材料としての利用が
検討されている。しかしながら、一般にフラーレンＣ
６０等は、対称性が良い為に発光が微弱であるという問
題点を有している。2. Description of the Related Art Fullerene has a large pi-electron conjugated system, and its use as a light emitting material utilizing its properties is being studied. However, generally, fullerene C
No. 60 has a problem that light emission is weak due to good symmetry.
【０００３】この発光が微弱であるという問題点を解決
するために、対称性の良いフラーレンに官能基を導入す
ることにより対称性を崩して発光を高める試みもされて
いるが、数多くの官能基を導入する必要がありそれらの
導入も容易ではなかった。In order to solve the problem that the luminescence is weak, attempts have been made to improve the luminescence by breaking the symmetry by introducing a functional group into fullerene having good symmetry. And their introduction was not easy either.
【０００４】一方、アジリジン基を持つフラレーン誘導
体としては、アリジリジン基の窒素原子に、４−アシル
−２，３，５，６−テトラフルオロ基が結合したもの
(M. Yan, S. X. Cai, and J. F. W. Keana, J. Org. Ch
em., 1994, 59, 5951-5954)、フェニル基及び４−シア
ノフェニル基 が結合したもの(J. Averdung and J. Mat
tay, Tetrahedron, 1996, 52, 5407-5420)や１，４−ビ
ス（２−アジドフェニル）−１，３−ブタジエン誘導体
とＣ６０とから合成されたビスアジドフラーレン誘導体
(G. Schick, T. Jarrosson, and Y. Rubin, Angew. Ch
em. Int. Ed. Engl., 1999, 38, 2360-2363)が知られて
いるが、それらの発光材料としての特性については報告
されてはいない。[0004] On the other hand, a fullerene derivative having an aziridine group is a derivative in which a 4-acyl-2,3,5,6-tetrafluoro group is bonded to a nitrogen atom of an arididine group.
(M. Yan, SX Cai, and JFW Keana, J. Org. Ch
em., 1994, 59, 5951-5954), with a phenyl group and a 4-cyanophenyl group bonded (J. Averdung and J. Mat.
tay, Tetrahedron, 1996, 52, 5407-5420) and 1,4-bis (2-azido-phenyl) -1,3-bis-azido fullerene derivative synthesized from butadiene derivatives and C 60 Metropolitan
(G. Schick, T. Jarrosson, and Y. Rubin, Angew. Ch
em. Int. Ed. Engl., 1999, 38, 2360-2363), but their properties as light emitting materials have not been reported.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、フラレーン
誘導体からなる新規な発光材料および窒素原子上に特定
な置換基を有するアジリジン官能基が導入された新規な
フラーレン誘導体を提供することを目的とする。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel luminescent material comprising a fullerene derivative and a novel fullerene derivative having an aziridine functional group having a specific substituent on a nitrogen atom. I do.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、上記課題
を達成するため鋭意検討した結果、フラーレンにアジリ
ジン官能基が一つ以上導入され、アジリジン官能基の窒
素原子上の置換基として芳香族基を有するフラレーン誘
導体が発光材料として有効であることを見出し、本発明
をなすに至った。Means for Solving the Problems The present inventors have conducted intensive studies to achieve the above object, and as a result, one or more aziridine functional groups have been introduced into fullerene, and aromatic groups have been substituted as substituents on the nitrogen atom of the aziridine functional group. The present inventors have found that a fullerene derivative having an aromatic group is effective as a light emitting material, and have accomplished the present invention.
【０００７】すなわち、本発明によれば、第一に、下記
一般式（１）で示されるフラーレン誘導体からなる発光
材料が提供されるThat is, according to the present invention, first, there is provided a luminescent material comprising a fullerene derivative represented by the following general formula (1).
【化３】 （Ａｒは芳香族基を、ｎは自然数を表す。） 第二に、上記フラーレン誘導体が、一般式（１）におい
て、Ａｒが、置換基を有してもよい芳香族単環炭化水素
基、置換基を有してもよい縮合多環芳香族炭化水素基、
置換基を有してもよい、芳香族性を示す複素単環基、置
換基を有してもよい、芳香族性を示す縮合複素環基から
選ばれた少なくとも一種であることを特徴とする第一の
発明の発光材料が提供される。第三に、Ａｒが、置換基
を有してもよい縮合多環芳香族炭化水素基であることを
特徴とする第二の発明の発光材料が提供される。第四
に、下記一般式（２）で示されるアジリジン官能基を有
するフラーレン誘導体が提供される。Embedded image (Ar represents an aromatic group and n represents a natural number.) Secondly, in the fullerene derivative, in the general formula (1), Ar represents an aromatic monocyclic hydrocarbon group which may have a substituent; A condensed polycyclic aromatic hydrocarbon group which may have a substituent,
It is characterized by being at least one selected from a heteromonocyclic group showing aromaticity which may have a substituent and a fused heterocyclic group showing aromaticity which may have a substituent. The luminescent material of the first invention is provided. Third, the luminescent material according to the second invention is provided, wherein Ar is a condensed polycyclic aromatic hydrocarbon group which may have a substituent. Fourth, a fullerene derivative having an aziridine functional group represented by the following general formula (2) is provided.
【化４】 （Ａｒは、置換基を有してもよい縮合多環芳香族炭化水
素基を表す。）Embedded image (Ar represents a condensed polycyclic aromatic hydrocarbon group which may have a substituent.)
【０００８】本発明の発光材料は、前記一般式（１）で
示されるフラーレン誘導体からなる。このフラレーン誘
導体は、フラーレンに導入したアジリジン官能基の窒素
原子に芳香族基が置換された構造を持つものである。従
来より、対称性の良いフラーレンに官能基を導入するこ
とにより対称性を崩して発光強度を上げる試みがなされ
ているが、この場合、一つの官能基の導入によりできる
だけ発光強度が増加するような官能基を選択する必要が
あるが、従来知られている官能基はフラーレンの発光強
度をさほど向上するものではなかった。本発明において
は、発光材料として、フラーレンに導入されたアジリジ
ン官能基の窒素原子上に芳香族基が置換されたものを選
定使用したことから、フラーレンの発光強度を著しく高
めることができる。The luminescent material of the present invention comprises a fullerene derivative represented by the above general formula (1). This fullerene derivative has a structure in which a nitrogen atom of the aziridine functional group introduced into fullerene is substituted with an aromatic group. Conventionally, attempts have been made to increase the emission intensity by introducing a functional group into fullerene having good symmetry, thereby breaking the symmetry and increasing the emission intensity as much as possible by introducing one functional group. It is necessary to select a functional group, but a conventionally known functional group does not significantly improve the emission intensity of fullerene. In the present invention, since a material in which an aromatic group is substituted on the nitrogen atom of the aziridine functional group introduced into fullerene is selected and used as the light emitting material, the light emission intensity of fullerene can be significantly increased.
【０００９】本発明の対象となる前記一般式（１）にお
いて、フラーレン（骨格）を形成するフラーレンとして
は、炭素のみより成るフラーレンの他に、これらのフラ
ーレンの炭素の一部を炭素以外の原子に変えたヘテロフ
ラーレン、これらのフラーレンの内部或いは外部に少な
くとも一つの原子が付着或いは結合しているフラーレン
類、フラーレンの炭素の一部を炭素以外の原子に変えた
ヘテロフラーレンの内部或いは外部に少なくとも一つの
原子が付着或いは結合しているヘテロフラーレンが包含
される。In the general formula (1), which is the object of the present invention, as the fullerene forming the fullerene (skeleton), in addition to the fullerene consisting of carbon only, a part of the carbon of these fullerenes may be an atom other than carbon. Heterofullerenes that have been changed to, fullerenes having at least one atom attached or bonded to the inside or outside of these fullerenes, or at least inside or outside of the heterofullerenes that have converted some carbons of fullerenes to atoms other than carbon. Heterofullerene to which one atom is attached or bonded is included.
【００１０】アジリジン官能基の導入個数（ｎ）につい
ても特別な制限は無いが、フラーレンＣ６０の場合で有
れば、好ましくは１−３０個、特に好ましくは１−６個
である。他のフラーレンについても同様の割合でアジリ
ジン官能基の導入を行うことが好ましい。[0010] There is no particular limitation on the number of introduced aziridine functional group (n), if there in the case of fullerene C 60, preferably 1-30, particularly preferably 1-6. It is preferable to introduce the aziridine functional group at the same ratio for other fullerenes.
【００１１】アジリジン官能基の窒素原子上に置換され
る基（Ａｒ）としては、フラーレン本体との間に立体
的、或いは電子的相互作用等を有する芳香族基が使用さ
れる。この芳香族基はパイ電子等の動きやすい電子を有
し、かつ、芳香族部位の置換位置を選択することにより
芳香族基とフラーレン本体との間の立体的、或いは電子
的相互作用等を調整することができる。As the group (Ar) substituted on the nitrogen atom of the aziridine functional group, an aromatic group having a steric or electronic interaction with the fullerene body is used. This aromatic group has a mobile electron such as a pi electron and adjusts the steric or electronic interaction between the aromatic group and the fullerene body by selecting the substitution position of the aromatic moiety. can do.
【００１２】芳香族基としては、例えば、置換基を有し
てもよい芳香族単環炭化水素基、置換基を有してもよい
縮合多環芳香族炭化水素基、置換基を有してもよい、芳
香族性を示す複素単環基、置換基を有してもよい、芳香
族性を示す縮合複素環基が挙げることができる。Examples of the aromatic group include an aromatic monocyclic hydrocarbon group which may have a substituent, a condensed polycyclic aromatic hydrocarbon group which may have a substituent, and a group having a substituent. And heterocyclic monocyclic groups showing aromaticity and condensed heterocyclic groups showing aromaticity which may have a substituent.
【００１３】芳香族単環炭化水素基としてはフェニル基
が、縮合多環芳香族炭化水素基としては、ナフチル基、
アントリル基、フェナントリル基等が、芳香族性を示す
複素単環基としては、フラニル基、チオフェニル基、ピ
ロリル基等のヘテロ原子を一つ含む五員環、ピリジニル
基等のヘテロ原子を一つ含む六員環、オキサゾリル基、
チアゾリル基等のヘテロ原子を二つ含む五員環、ピリダ
ジニル基、ピリミジニル基等のヘテロ原子を二つ含む六
員環、その他、ヘテロ原子を少なくとも一つ含む五、
六、七員環が、芳香族性を示す縮合複素環基としては、
インドリル基、キノリニル基等のヘテロ原子を一つ含む
二環性縮合複素基、キノキサリニル基等のヘテロ原子を
二つ含む二環性縮合複素基、アクリジニル基等のヘテロ
原子を一つ含む三環性縮合複素基、インダゾリル基等の
ヘテロ原子を二つ含む二環性縮合複素基、その他、ヘテ
ロ原子を少なくとも一つ含む多環性縮合複素基等が例示
される。また、置換基としては、特に限定されないが、
アルキル基、アリール基、カルボキシ基、スルホニル
基、アルコキシカルボニル基、カルバモイル基、イミド
基、アミジノ基、シアノ基、イソシアノ基、ホルミル
基、カルボニル基、チオカルボニル基、ヒドロキシ基、
メルカプト基、アミノ基、イミノ基、アルコキシ基、ア
ルキルチオ基、ハロゲン基、ニトロ基等が例示される。
またその数も限定されるものではなく芳香族基に置換基
が一つ以上有れば良く、また、芳香族基に置換基が無く
ても良い。As the aromatic monocyclic hydrocarbon group, a phenyl group is used, and as the condensed polycyclic aromatic hydrocarbon group, a naphthyl group,
An anthryl group, a phenanthryl group, etc., as a heteromonocyclic group exhibiting aromaticity, include one hetero atom such as a furanyl group, a thiophenyl group, a hetero atom such as a pyrrolyl group, and a hetero atom such as a pyridinyl group. 6-membered ring, oxazolyl group,
Five-membered ring containing two heteroatoms such as thiazolyl group, pyridazinyl group, six-membered ring containing two heteroatoms such as pyrimidinyl group, etc.
Six- or seven-membered ring, as a fused heterocyclic group showing aromaticity,
Bicyclic fused hetero group containing one hetero atom such as indolyl group, quinolinyl group, bicyclic fused hetero group containing two hetero atoms such as quinoxalinyl group, tricyclic containing one hetero atom such as acridinyl group Examples include a fused heterocyclic group containing two hetero atoms such as a fused hetero group and an indazolyl group, and a polycyclic fused hetero group containing at least one hetero atom. Further, the substituent is not particularly limited,
Alkyl group, aryl group, carboxy group, sulfonyl group, alkoxycarbonyl group, carbamoyl group, imide group, amidino group, cyano group, isocyano group, formyl group, carbonyl group, thiocarbonyl group, hydroxy group,
Examples thereof include a mercapto group, an amino group, an imino group, an alkoxy group, an alkylthio group, a halogen group, and a nitro group.
The number is not limited, and the aromatic group may have at least one substituent, and the aromatic group may not have a substituent.
【００１４】本発明の発光材料は前記一般式（１）で示
されるフラーレン誘導体の全てが使用できるが、好まし
くは、Ａｒが置換基を有してもよい芳香族単環炭化水素
基、置換基を有してもよい縮合多環芳香族炭化水素基、
置換基を有してもよい、芳香族性を示す複素単環基、置
換基を有してもよい、芳香族性を示す縮合複素環基のも
の、更に好ましくはＡｒが、置換基を有してもよい縮合
多環芳香族炭化水素基のものすなわち前記一般式（２）
で示されるフラーレン誘導体が使用される。As the luminescent material of the present invention, all of the fullerene derivatives represented by the above general formula (1) can be used, but it is preferable that Ar is an aromatic monocyclic hydrocarbon group which may have a substituent, A condensed polycyclic aromatic hydrocarbon group which may have
An aromatic heterocyclic monocyclic group which may have a substituent, a condensed aromatic heterocyclic group which may have a substituent, and more preferably Ar has a substituent Of a condensed polycyclic aromatic hydrocarbon group, ie, the above-mentioned general formula (2)
Are used.
【００１５】本発明の発光材料は、例えば二枚の薄膜電
極等の間に高分子電解質等と混入した薄膜を形成するこ
とにより有機発光ダイオードなどの発光体として使用す
ることができる。また、基盤上に本発明の発光材料で薄
膜を形成することによりフォトルミネッセンス材料とし
て用いることもできる。The light emitting material of the present invention can be used as a light emitting body such as an organic light emitting diode by forming a thin film mixed with a polymer electrolyte or the like between two thin film electrodes or the like. Further, a thin film formed of the light emitting material of the present invention on a substrate can be used as a photoluminescent material.
【００１６】本発明の前記一般式（１）及び一般式
（２）で示されるフラレーン誘導体は、フラーレンと芳
香族アジドの熱反応によりＮ−アリールアザフラーロイ
ドを合成し、この化合物を光化学的転位反応させること
により合成することができる。具体的には、一般式
（２）において、フラーレンがＣ６０でＡｒがフェニル
基の化合物は、６０〜１００℃のＣ６０の１，２−ジク
ロロベンゼン溶液にフェニルアジドの１，２−ジクロロ
ベンゼン溶液を滴下してＮ−フェニルアザ−［６０］フ
ラーロイドを合成し、このトルエン溶液に紫外線照射を
行うことにより合成すればよい。The fullerene derivatives represented by the general formulas (1) and (2) of the present invention synthesize N-arylazafulleroids by a thermal reaction between fullerene and aromatic azide, and this compound is subjected to photochemical rearrangement. It can be synthesized by reacting. Specifically, in the general formula (2), fullerene compound of Ar is a phenyl group in C 60 may, of 60 to 100 [° C. C 60 1,2-dichlorobenzene solution of phenyl azide 1,2-dichlorobenzene The solution may be added dropwise to synthesize N-phenylaza- [60] fulleroid, and the toluene solution may be irradiated with ultraviolet light to synthesize.
【００１７】[0017]
【実施例】次に実施例に基づき、本発明を更に詳細に説
明する。Next, the present invention will be described in more detail with reference to examples.
【００１８】実施例１ フラーレンＣ６０とフェニルアジドを原料としてＮ−フ
ェニルアザ−［６０］フラーロイドを合成し、このトル
エン溶液に紫外線照射を行うことよりフェニルアジリジ
ニル基を導入し、１，２−（Ｎ−フェニルアジリジノ）
−［６０］フラーレンを合成した。フォトルミネッセン
ス発光材料としての特性を調べるために、この化合物の
１０−４Ｍトルエン溶液を調整して５００ｎｍ光で励起
した所、６９０ｎｍにおける発光強度は１２３カウント
であった。[0018] Example 1 fullerene C 60 and N- Feniruaza phenyl azide as a raw material - [60] was synthesized Furaroido, introducing phenyl aziridinyl group from carrying out the ultraviolet irradiation to the toluene solution, 1,2 (N-phenylaziridino)
-[60] Fullerene was synthesized. In order to examine the properties as a photoluminescent light emitting material, a 10 -4 M toluene solution of this compound was adjusted and excited with 500 nm light, and the emission intensity at 690 nm was 123 counts.
【００１９】実施例２ フラーレンＣ６０と１−アジドナフタレンを原料として
Ｎ−１−ナフチルアザ−［６０］フラーロイドを合成
し、このトルエン溶液に紫外線照射を行うことにより１
−ナフチルアジリジニル基を導入し、１，２−（Ｎ−１
−ナフチルアジリジノ）−［６０］フラーレンを合成し
た。このものを実施例１と同様にフォトルミネッセンス
発光材料としての特性を調べたところ発光強度は５００
カウントであった。[0019] Example 2 fullerene C 60 with 1-azido-N-1- Nafuchiruaza naphthalene as a raw material - [60] was synthesized Furaroido, 1 by performing UV irradiation to the toluene solution
-A naphthyl aziridinyl group was introduced to form 1,2- (N-1
-Naphthylaziridino)-[60] fullerene was synthesized. This was examined for characteristics as a photoluminescent light-emitting material in the same manner as in Example 1.
It was a count.
【００２０】実施例３ フラーレンＣ６０と２−アジドナフタレンを原料として
Ｎ−２−ナフチルアザ−［６０］フラーロイドを合成
し、このトルエン溶液に紫外線照射を行うことにより、
２−ナフチルアジリジニル基を導入し、１，２−（Ｎ−
２−ナフチルアジリジノ）−［６０］フラーレンを合成
した。このものを実施例１と同様にフォトルミネッセン
ス発光材料としての特性を調べたところ発光強度は６２
カウントであった。[0020] N-2- Nafuchiruaza between Example 3 fullerene C 60 2-azido-naphthalene as a raw material - [60] was synthesized Furaroido, by performing UV irradiation to the toluene solution,
By introducing a 2-naphthyl aziridinyl group, 1,2- (N-
2-Naphthylaziridino)-[60] fullerene was synthesized. When the characteristics of this material as a photoluminescence light emitting material were examined in the same manner as in Example 1, the light emission intensity was 62%.
It was a count.
【００２１】比較例１ フラーレンＣ６０について、実施例１と同様の測定を行
った所、発光強度は、４８カウントであった。[0021] Comparative Example 1 fullerene C 60, was subjected to the same measurements as in Example 1, the emission intensity was 48 counts.
【００２２】[0022]
【発明の効果】本発明においては、発光材料として、フ
ラーレンに導入されたアジリジン官能基の窒素原子上に
芳香族基が置換されたものを選定使用したことから、フ
ラーレンの発光強度を著しく高めることができる。According to the present invention, a material in which an aromatic group is substituted on the nitrogen atom of the aziridine functional group introduced into fullerene is selected and used as a luminescent material. Can be.
Claims (4)
導体からなる発光材料。 【化１】 （Ａｒは芳香族基を、ｎは自然数を表す。）1. A luminescent material comprising a fullerene derivative represented by the following general formula (1). Embedded image (Ar represents an aromatic group, and n represents a natural number.)
おいて、Ａｒが、置換基を有してもよい芳香族単環炭化
水素基、置換基を有してもよい縮合多環芳香族炭化水素
基、置換基を有してもよい、芳香族性を示す複素単環
基、置換基を有してもよい、芳香族性を示す縮合複素環
基から選ばれた少なくとも一種であることを特徴とする
請求項１の発光材料。2. The fullerene derivative according to claim 1, wherein in the general formula (1), Ar is an aromatic monocyclic hydrocarbon group optionally having a substituent, or a condensed polycyclic aromatic hydrocarbon group optionally having a substituent. A hydrogen group, which may have a substituent, an aromatic heterocyclic monocyclic group, which may have a substituent, which may be at least one selected from fused aromatic heterocyclic groups which have an aromatic property; The luminescent material according to claim 1, wherein:
香族炭化水素基であることを特徴とする請求項２の発光
材料。3. The luminescent material according to claim 2, wherein Ar is a condensed polycyclic aromatic hydrocarbon group which may have a substituent.
能基を有するフラーレン誘導体。 【化２】 （Ａｒは、置換基を有してもよい縮合多環芳香族炭化水
素基を表す。）4. A fullerene derivative having an aziridine functional group represented by the following general formula (2). Embedded image (Ar represents a condensed polycyclic aromatic hydrocarbon group which may have a substituent.)
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005263692A (en) * | 2004-03-18 | 2005-09-29 | Mitsubishi Chemicals Corp | Fullerene derivative and photoelectric converting material |
| WO2009066642A1 (en) * | 2007-11-19 | 2009-05-28 | Toppan Printing Co., Ltd. | Photoresponsive base having triazole skeleton |
| JP2009260045A (en) * | 2008-04-17 | 2009-11-05 | National Institute Of Advanced Industrial & Technology | Organic thin-film solar cell |
| RU2484010C2 (en) * | 2011-06-16 | 2013-06-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | METHOD OF PRODUCING 1-IODO-2-AZIDO(C60-Ih)[5,6]FULLERENE |
| RU2594562C2 (en) * | 2014-12-11 | 2016-08-20 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Method for producing n-arylaziridinum[2 ', 3 ': 1.9]fullerene [60] |
| RU2596876C2 (en) * | 2014-12-10 | 2016-09-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Method of producing aziridino[2',3':1,9]fullerenes[60], containing framework and polycyclic substitutes |
-
2000
- 2000-09-06 JP JP2000270030A patent/JP3511092B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005263692A (en) * | 2004-03-18 | 2005-09-29 | Mitsubishi Chemicals Corp | Fullerene derivative and photoelectric converting material |
| WO2009066642A1 (en) * | 2007-11-19 | 2009-05-28 | Toppan Printing Co., Ltd. | Photoresponsive base having triazole skeleton |
| JP2009260045A (en) * | 2008-04-17 | 2009-11-05 | National Institute Of Advanced Industrial & Technology | Organic thin-film solar cell |
| RU2484010C2 (en) * | 2011-06-16 | 2013-06-10 | Учреждение Российской Академии Наук Институт Нефтехимии И Катализа Ран | METHOD OF PRODUCING 1-IODO-2-AZIDO(C60-Ih)[5,6]FULLERENE |
| RU2596876C2 (en) * | 2014-12-10 | 2016-09-10 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Method of producing aziridino[2',3':1,9]fullerenes[60], containing framework and polycyclic substitutes |
| RU2594562C2 (en) * | 2014-12-11 | 2016-08-20 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Method for producing n-arylaziridinum[2 ', 3 ': 1.9]fullerene [60] |
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|---|---|
| JP3511092B2 (en) | 2004-03-29 |
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