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
Author(s)
조대원임숙현이진주나춘섭남기평이가예[이가예]김진흥[김진흥]윤웅찬[윤웅찬]Patrick S Mariano[Patrick S Mariano]
Keywords
TERTIARY-AMINES; METAL-FREE; DERIVATIVES; FUNCTIONALIZATION; PHOTOCHEMISTRY; CHEMISTRY; PATHWAYS; C60; PHOTOREACTIONS; TRANSISTORS
Issue Date
201506
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Citation
TETRAHEDRON LETTERS, v.56, no.23, pp.3014 - 3018
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.
URI
http://hdl.handle.net/YU.REPOSITORY/32088http://dx.doi.org/10.1016/j.tetlet.2014.10.060
ISSN
0040-4039
Appears in Collections:
이과대학 > 화학생화학부 > Articles
문과대학 > 중국언어문화학과 > Articles
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