Exploring the photoinduced electron transfer reactivity of aza[60]fullerene iminium cation
Photolysis of (C 59N) 2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]full...
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| Veröffentlicht in: | Tetrahedron 2010-11, Vol.66 (48), p.9363-9369 |
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| creator | Roubelakis, Manolis M. Vougioukalakis, Georgios C. Nye, Leanne C. Drewello, Thomas Orfanopoulos, Michael |
| description | Photolysis of (C
59N)
2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]fullerene, followed by radical coupling of the resulting aza[60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C
59N
+, affording the corresponding aza[60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and β,β-dimethylstyrene, [2+2] cycloaddition reactions with the aza[60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2010.10.006 |
| format | Article |
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59N)
2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]fullerene, followed by radical coupling of the resulting aza[60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C
59N
+, affording the corresponding aza[60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and β,β-dimethylstyrene, [2+2] cycloaddition reactions with the aza[60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts.
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59N)
2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]fullerene, followed by radical coupling of the resulting aza[60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C
59N
+, affording the corresponding aza[60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and β,β-dimethylstyrene, [2+2] cycloaddition reactions with the aza[60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts.
[Display omitted]</description><subject>Aromatic compounds</subject><subject>Azafullerene</subject><subject>Benzyltrimethylsilanes</subject><subject>Carbon</subject><subject>Cations</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Coupling (molecular)</subject><subject>Cross-disciplinary physics: materials science; rheology</subject><subject>Derivatives</subject><subject>Electron transfer</subject><subject>Electron-rich olefins</subject><subject>Exact sciences and technology</subject><subject>Free radicals chemistry</subject><subject>Fullerenes and related materials; diamonds, graphite</subject><subject>General and physical chemistry</subject><subject>Iminium cation</subject><subject>Materials science</subject><subject>Olefins</subject><subject>Organic chemistry</subject><subject>Photochemistry</subject><subject>Photoinduced electron transfer</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Physics</subject><subject>Radicals</subject><subject>Reactivity and mechanisms</subject><subject>Specific materials</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKQzEQhoMoWC8P4C4bwc2pubfFlYg3ENzoRpGQkzPRlNOkJjlFfXpTKy5dDTN8_wzzIXREyZgSqk7n4wJlzMhPPyZEbaERFUo0UlC1jUaECNIIwsgu2st5TgihlPERerr8WPYx-fCKyxvg5Vss0YdusNBh6MGWFAMuyYTsIOEExha_8uUTR4fNl3lW5MUNfQ8JAmC_8MEPC2xN8TEcoB1n-gyHv3UfPV5dPlzcNHf317cX53eNFUyVRjAxoxNnJYW2a6UF6piSdDppbcs7w2Zm2rXApeTSSCnAcspaCRL4FLqZa_k-OtnsXab4PkAueuGzhb43AeKQNZ0IoWbVjKgo3aA2xZwTOL1MfmHSp6ZErz3qua4e9drjelQ91szx73qTrelddWF9_gsyzqdMsTV3tuGg_rrykHS2HkIV6VP1qLvo_7nyDT7cidk</recordid><startdate>20101127</startdate><enddate>20101127</enddate><creator>Roubelakis, Manolis M.</creator><creator>Vougioukalakis, Georgios C.</creator><creator>Nye, Leanne C.</creator><creator>Drewello, Thomas</creator><creator>Orfanopoulos, Michael</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20101127</creationdate><title>Exploring the photoinduced electron transfer reactivity of aza[60]fullerene iminium cation</title><author>Roubelakis, Manolis M. ; 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59N)
2 solutions in the presence of neutral π-donors, such as arenes and electron-rich alkenes leads to a series of novel aza[60]fullerene monoadducts. The key step of the reaction involves a photoinduced electron transfer from the donor molecule to the iminium cation of aza[60]fullerene, followed by radical coupling of the resulting aza[60]fullerenyl radical with an intermediate stabilized radical derived from the substrate. This type of reactivity has been proven efficient with arenes having oxidation potential higher than about 1.5 V. Simple olefins, such as tri- and tetra-methylethylene, as well as cyclohexene, can also participate in this kind of photoinduced electron transfer-initiated reaction with C
59N
+, affording the corresponding aza[60]fullerene derivatives. In the case of 2-methoxyprop-1-ene, 2,4-hexadiene, and β,β-dimethylstyrene, [2+2] cycloaddition reactions with the aza[60]fullerene carbon shell dominate, leading to a mixture of unidentified multiadducts.
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| subjects | Aromatic compounds Azafullerene Benzyltrimethylsilanes Carbon Cations Chemical reactivity Chemistry Coupling (molecular) Cross-disciplinary physics: materials science rheology Derivatives Electron transfer Electron-rich olefins Exact sciences and technology Free radicals chemistry Fullerenes and related materials diamonds, graphite General and physical chemistry Iminium cation Materials science Olefins Organic chemistry Photochemistry Photoinduced electron transfer Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Physics Radicals Reactivity and mechanisms Specific materials |
| title | Exploring the photoinduced electron transfer reactivity of aza[60]fullerene iminium cation |
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