Synthesis and photosensitizing properties of porphycene with imidazolium tag

Hisashi Shimakoshi, Kenichi Sasaki, Yusuke Iseki, Yoshio Hisaeda

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6 Citations (Scopus)


Porphycene having an imidazolium cation tag was synthesized and characterized by elemental analysis, UV-vis, NMR and ESI-mass spectroscopies. This porphycene derivative easily dissolves in various ionic liquids and produces singlet oxygen under irradiation by visible light (λ < 460 nm). The photophysical parameters of the porphycene in ionic liquids were determined and the values were compared to those in acetonitrile. Photosensitizing reactions using this new porphycene for the oxidation of 1,5-dihydroxynaphthalene in ionic liquids were investigated and found to form 5-hydroxy-1,4-naphthoquinone. The recycled use of the porphycene was efficiently achieved in N,N,N-trimethyl-N-propylammonium bis(trifluoromethanesulfonyl)amide ([TMPA][TFSA]) and N-methyl-N-propyl-piperidinium bis(trifluoromethanesulfonyl) amide ([P13][TFSA]).

Original languageEnglish
Pages (from-to)530-536
Number of pages7
JournalJournal of Porphyrins and Phthalocyanines
Issue number5-6
Publication statusPublished - 2012

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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