Singlet Oxygen Involvement in the Photochemical Reaction of C60 and Amines. Synthesis of an Alkyne-Containing Fullerene

被引：0

作者：

Department of Chemistry, University of California, Los Angeles, CA 90095-1569, United States ^{[1
]}

机构：

来源：

J Phys Chem A | / 36卷 / 7244-7247期

关键词：

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Photochemical addition of 3-diethylamino-l-propyne (DEAP) to C60 leads to a novel fullerene adduct (1). The addition of DEAP to C60 did not occur in the expected [2+2] fashion. Instead, addition took place at the methylene carbons alpha to the nitrogen, resulting in the replacement of two C-H bonds with C60-C bonds. This reaction provides a facile route to a fullerene adduct containing an alkyne moiety. Study of the mechanism of addition disclosed the unexpected involvement of singlet oxygen. Other previously reported additions of amines to fullerenes also appear to involve singlet oxygen.

引用

共 50 条

[41] Photochemical Approach for the Preparation of N-Alkyl/Aryl Substituted Fulleropyrrolidines: Photoaddition Reactions of Silyl Group Containing α-Aminonitriles with Fullerene C60
Lim, Suk Hyun
Oh, Jiin
Nahm, Keepyung
Noh, Sunguk
Shim, Jun Ho
Kim, Cheolhee
Kim, Eunae
Cho, Dae Won
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (03): : 1407 - 1420
[42] Nickel-promoted first ene-diyne cycloaddition reaction on C60:: Synthesis and photochemistry of the fullerene derivatives
Hsiao, TY
Santhosh, KC
Liou, KF
Cheng, CH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) : 12232 - 12236
[43] The photochemical reaction of 1,2-digermacyclobutane with C60: possible example of a closed [6,5]-bridged fullerene derivative of germacyclopropane
Kabe, Y
Ohgaki, H
Yamagaki, T
Nakanishi, H
Ando, W
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 636 (1-2) : 82 - 90
[44] Reaction of 1,1′-bis(diazoacetyl)ferrocene with C60 fullerene:: synthesis of conformationally rigid fullerene-ferrocene ansa-derivative
Sokolov, VI
Potolokova, TV
Nefedova, MN
Peregudov, AS
RUSSIAN CHEMICAL BULLETIN, 2003, 52 (06) : 1452 - 1453
[45] Synthesis, Photophysical Properties, and Photochemical Activity of the Water-Soluble Dyad Based on Fullerene C60 and Chlorin &ITe&IT6 Derivatives
Belik, A. Yu.
Mikhailov, P. A.
Kraevaya, O. A.
Rybkin, A. Yu.
Khakina, E. A.
Goryachev, N. S.
Usol'tseva, L. I.
Romanenko, Yu. V.
Koifman, O. I.
Gushchina, O. I.
Mironov, A. F.
Troshin, P. A.
Kotel'nikov, A. I.
DOKLADY PHYSICAL CHEMISTRY, 2017, 477 : 222 - 226
[46] A selective synthesis of the fullerene-fused dioxane adduct via heterogeneous reaction of C60 with α-diols and NaOH under ultrasonication
Kinzyabaeva, Zemfira S.
Sharipov, Glus L.
ULTRASONICS SONOCHEMISTRY, 2018, 42 : 119 - 123
[47] Synthesis of fullerene alkoxy derivatives by free-radical reaction of C60 with aliphatic alcohols promoted by chromium(VI) compounds
Bulgakov, R. G.
Kinzyabaeva, Z. S.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (05) : 762 - 764
[48] Synthesis of fullerene alkoxy derivatives by free-radical reaction of C60 with aliphatic alcohols promoted by chromium(VI) compounds
R. G. Bulgakov
Z. S. Kinzyabaeva
Russian Journal of Organic Chemistry, 2014, 50 : 762 - 764
[49] Growth of Fullerene Fragments Using the Diels-Alder Cycloaddition Reaction: First Step towards a C60 Synthesis by Dimerization
Mojica, Martha
Mendez, Francisco
Alonso, Julio A.
MOLECULES, 2013, 18 (02): : 2243 - 2254
[50] Synthesis of fullerene γ-Lactones by Free Radical Reaction of C60 with Ketones Promoted by Compounds of Transition Metals Cr(VI), Ce(IV)
Bulgakov, R. G.
Kinzyabaeva, Z. S.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (08) : 1189 - 1193

← 1 2 3 4 5 →