Synthesis and properties of amino acid functionalized water-soluble perylene diimides

Yongshan Ma; Xuemei Li; Xiaofeng Wei; Tianyi Jiang; Junsen Wu; Huixue Ren

Korean Journal of Chemical Engineering, Vol.32, No.7, 1427-1433, July, 2015

DOI10.1007/s11814-014-0355-1 Export Citation

Synthesis and properties of amino acid functionalized water-soluble perylene diimides

Yongshan Ma^†, Xuemei Li, Xiaofeng Wei, Tianyi Jiang, Junsen Wu, and Huixue Ren

School of Municipal and Environmental Engineering, Shandong Jianzhu University, Jinan 250101, P. R. China

E-mail:

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.

Keywords:Water-soluble Perylene Diimides;Synthesis;Absorption Spectrum;Fluorescence Spectrum;DFT Calculations;Living Cell Staining

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[13] Rui F, Carlos R, Maria C, Manuel M, Maria F, RSC Adv., 3, 24535 (2013)

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[23] Liu L, Zhang X, Acta Phys. Chim. Sin., 28, 283 (2012)