SET-promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines with fullerene C<inf>60</inf>. Electronic factors that govern photoaddition efficiencies
- 주제(키워드) Fullerene , Ion-radicals , SET-photochemistry , α-Silylamines
- 등재 SCIE, SCOPUS
- 발행기관 Elsevier Ltd
- 발행년도 2015
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000115819
- 본문언어 영어
- Published As http://dx.doi.org/10.1016/j.tetlet.2014.10.060
- 저작권 이화여자대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
Single electron transfer (SET) promoted photoaddition reactions of N-α-trimethylsilylmethyl-N,N-dibenzylamines to fullerene C<inf>60</inf> 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<inf>60</inf> anion radical intermediates by a pathway initiated by excited state SET. SET is followed by desilylation of the aminium radicals to produce α-amino radicals that couple with either C<inf>60</inf> or its radical anion to form precursors of the 1,2-adducts. The electronic nature of para-substituents on the aryl ring of N-α-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. © 2014 Published by Elsevier Ltd.
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