Efficient Green Synthesis and Properties of Perylene Red
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TQ613.7; O625.52

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State Administrate of Science, Technology & Industry for Chinese National Defense (Technical Basis Project, No. JSJL2015212A-001); Sichuan Province Academic and Technical Leaders Fund (2015)

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    Abstract:

    Intermediate N,N’-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4,9,10- tetracarboxylic acid diimide (BDIP-TCPBI) and product N,N’-bis(2,6-diisopropylphenyl)- 1,6,7,12-tetraphenoxyperylene-3,4,9,10-tetracarboxylic acid diimide (perylene red) were synthesized from commercially available 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic bisanhydride (TCPBA), and their structures were characterized with IR, MS and NMR spectra. The reaction time of BDIP-TCPBI was shortened by half and its purity was increased by 23% in the presence of zinc acetate dihydrate as catalyst. The optimum synthesis conditions of BDIP-TCPBI were determined that the molar ratio of n(TCPBA) : n(2,6-Diisopropylaniline) : n(zinc acetate dihydrate) : n(propionic acid) was 1:4:0.2:107 for 12 h at 120°C, the yield and purity of BDIP-TCPBI were 88% and 84%, respectively. Using a simple washing method instead of column chromatography, the purity of perylene red was increased by 10%. This preparation was efficient, green and valuable in practical application. The spectra study indicated that the stokes shift of perylene red was 35 nm. From the estimation of cyclic voltammetry, the LUMO and HOMO orbital energy levels of perylene red were -4.144 eV and -4.470 eV, respectively. Perylene red was a potential electron acceptor material with a weak fluorescence self-absorption.

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History
  • Received:July 11,2017
  • Revised:September 07,2017
  • Adopted:September 21,2017
  • Online: February 28,2018
  • Published:
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