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SET-promoted photoaddition reactions of N-alpha-trimethylsilylmethyl-N, N-dibenzylamines with fullerene C-60. Electronic factors that govern photoaddition efficiencies

Title
SET-promoted photoaddition reactions of N-alpha-trimethylsilylmethyl-N, N-dibenzylamines with fullerene C-60. Electronic factors that govern photoaddition efficiencies
Authors
Lim, Suk HyunYi, JinjuRa, Choon SupNahm, KeepyungCho, Dae WonLee, Ga YeKim, JinheungYoon, Ung ChanMariano, Patrick S.
Ewha Authors
김진흥
SCOPUS Author ID
김진흥scopus
Issue Date
2015
Journal Title
TETRAHEDRON LETTERS
ISSN
0040-4039JCR Link
Citation
vol. 56, no. 23, pp. 3014 - 3018
Keywords
FullereneSET-photochemistryalpha-SilylaminesIon-radicals
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Single electron transfer (SET) promoted photoaddition reactions of N-alpha-trimethylsilylmethyl-N,N-dibenzylamines to fullerene C-60 were investigated as part of an effort aimed at developing a general method to prepare various aryl ring containing aminomethylfullerenes and exploring factors that govern photoaddition efficiencies. The results show that the photoaddition reactions take place highly efficiently to form 1,2-adducts. The mechanism for this process involves generation of aminium radicals and C-60 anion radical intermediates by a pathway initiated by excited state SET. SET is followed by desilylation of the aminium radicals to produce alpha-amino radicals that couple with either C-60 or its radical anion to form precursors of the 1,2-adducts. The electronic nature of para-substituents on the aryl ring of N-alpha-trimethylsilylmethyl-N,N-dibenzylamines has a pronounced effect on the efficiency of the photoaddition reaction, with electron donating groups causing a greater than 2-fold enhancement compared to that brought about by electron withdrawing groups. (C) 2014 Published by Elsevier Ltd.
DOI
10.1016/j.tetlet.2014.10.060
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자연과학대학 > 화학·나노과학전공 > Journal papers
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