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- 저자 : Yongshan Ma (검색결과 1 건)
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Synthesis and properties of amino acid functionalized water-soluble perylene diimides
Yongshan Ma,Xuemei Li,Xiaofeng Wei,Tianyi Jiang,Junsen Wu,Huixue Ren 한국화학공학회 2015 Korean Journal of Chemical Engineering Vol.32 No.7
We prepared amino acid functionalized water-soluble perylene diimides: N,N'-bi(L-glutamic acid)-perylene- 3,4;9,10-dicarboxylic diimide (1), N,N'-bi(L-phenylalanine acid)-perylene-3,4;9,10-dicarboxylic diimide (2), N,N'-bi(Lglutamic amine)-perylene-3,4;9,10-dicarboxylic diimide (3) and N,N'-bi(L-phenylalanine amine)-perylene-3,4;9,10- dicarboxylic diimide (4). The structures of 3 and 4 were confirmed by 1H NMR, FT-IR and MS. The maximal absorption bands of compound 1 and 2 in concentrated sulfuric acid were red-shifted for about 48 and 74 nm, respectively, compared with that of Perylene-3,4,9,10-tetracarboxylic acid dianhydride (PTCDA). Nearly no fluorescence was observed for compounds 1 and 2 in water, while compounds 3 and 4 were significantly water-soluble and had very high fluorescent quantum. The mechanism of the optical properties change was discussed, and the π-π stacking caused by H+ led to the changes of fluorescence spectrum and absorption spectrum. The calculated molecular orbital energies and the frontier molecular orbital maps of compounds 1-2 based on density function theory (DFT) calculations were reported. Owing to the high water-soluble, the perylene derivatives 3 and 4 were successfully applied as high-performance fluorochromes for living hela cells imaging.
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