Cycloaddition of hexacene and fullerene[60]

Wei Ting Su; Motonori Watanabe; Yuan Jay Chang; Po Ting Chou; Avijit Ghosh; Tahsin J. Chow

doi:10.1016/j.tetlet.2015.01.093

Cycloaddition of hexacene and fullerene[60]

Wei Ting Su, Motonori Watanabe, Yuan Jay Chang, Po Ting Chou, Avijit Ghosh, Tahsin J. Chow

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

The [4+2] cycloaddition of hexacene and C₆₀ yielded 1:1 and 1:2 adducts. The highest yield of 1:1 adduct was 90% by heating hexacene and C₆₀ in toluene. The formation of 2 was achieved by reacting 1 with an excess amount of C₆₀ in the presence of silica gel 60 with a yield up to 69%. The function of silica gel was rationalized by the effect of concentration enhancement inside the pore of silica gel. The reaction was examined systematically by changing the parameters of solvent, temperature, reaction time, and the pore size of silica gel. Both purified compounds 1 and 2 can be used for the fabrication of bulk heterojunction solar cells.

Original language	English
Pages (from-to)	1092-1095
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	9
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.093
Publication status	Published - Feb 25 2015

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.01.093

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title = "Cycloaddition of hexacene and fullerene[60]",

abstract = "The [4+2] cycloaddition of hexacene and C60 yielded 1:1 and 1:2 adducts. The highest yield of 1:1 adduct was 90% by heating hexacene and C60 in toluene. The formation of 2 was achieved by reacting 1 with an excess amount of C60 in the presence of silica gel 60 with a yield up to 69%. The function of silica gel was rationalized by the effect of concentration enhancement inside the pore of silica gel. The reaction was examined systematically by changing the parameters of solvent, temperature, reaction time, and the pore size of silica gel. Both purified compounds 1 and 2 can be used for the fabrication of bulk heterojunction solar cells.",

author = "Su, {Wei Ting} and Motonori Watanabe and Chang, {Yuan Jay} and Chou, {Po Ting} and Avijit Ghosh and Chow, {Tahsin J.}",

note = "Funding Information: This work was supported by the Ministry of Science and Technology of Taiwan and Academia Sinica . We thank Professors S.-H. Chiu and K. Pitchumani for helpful discussions. MW thanks a support from I 2 CNER, MEXT , Japan. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

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doi = "10.1016/j.tetlet.2015.01.093",

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T1 - Cycloaddition of hexacene and fullerene[60]

AU - Su, Wei Ting

AU - Watanabe, Motonori

AU - Chang, Yuan Jay

AU - Chou, Po Ting

AU - Ghosh, Avijit

AU - Chow, Tahsin J.

N1 - Funding Information: This work was supported by the Ministry of Science and Technology of Taiwan and Academia Sinica . We thank Professors S.-H. Chiu and K. Pitchumani for helpful discussions. MW thanks a support from I 2 CNER, MEXT , Japan. Publisher Copyright: © 2015 Elsevier Ltd. All rights reserved. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2015/2/25

Y1 - 2015/2/25

N2 - The [4+2] cycloaddition of hexacene and C60 yielded 1:1 and 1:2 adducts. The highest yield of 1:1 adduct was 90% by heating hexacene and C60 in toluene. The formation of 2 was achieved by reacting 1 with an excess amount of C60 in the presence of silica gel 60 with a yield up to 69%. The function of silica gel was rationalized by the effect of concentration enhancement inside the pore of silica gel. The reaction was examined systematically by changing the parameters of solvent, temperature, reaction time, and the pore size of silica gel. Both purified compounds 1 and 2 can be used for the fabrication of bulk heterojunction solar cells.

AB - The [4+2] cycloaddition of hexacene and C60 yielded 1:1 and 1:2 adducts. The highest yield of 1:1 adduct was 90% by heating hexacene and C60 in toluene. The formation of 2 was achieved by reacting 1 with an excess amount of C60 in the presence of silica gel 60 with a yield up to 69%. The function of silica gel was rationalized by the effect of concentration enhancement inside the pore of silica gel. The reaction was examined systematically by changing the parameters of solvent, temperature, reaction time, and the pore size of silica gel. Both purified compounds 1 and 2 can be used for the fabrication of bulk heterojunction solar cells.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Cycloaddition of hexacene and fullerene[60]

Abstract

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