TY - JOUR
T1 - Synthesis and photosensitizing properties of porphycene with imidazolium tag
AU - Shimakoshi, Hisashi
AU - Sasaki, Kenichi
AU - Iseki, Yusuke
AU - Hisaeda, Yoshio
N1 - Funding Information:
This study was partially supported by the Global COE Program “Science for Future Molecular Systems,” a Grant-in-Aid for Scientific Research on Priority Areas (452) and Innovative Areas (2204) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan, and a Grant-in-Aid for Scientific Research (C) (No. 23550125) and (A) (No. 21245016) from the Japan Society for the Promotion of Science (JSPS). We thank Prof. N. Nakashima and Prof. T. Fujigaya, Kyushu University, for helping to measure the photoluminescence spectra. We also thank Dr. M. Kanakubo, National Institute of Advanced Industrial Science and Technology, for his helpful discussion.
PY - 2012
Y1 - 2012
N2 - 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]).
AB - 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]).
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U2 - 10.1142/S1088424612500551
DO - 10.1142/S1088424612500551
M3 - Article
AN - SCOPUS:84862904245
SN - 1088-4246
VL - 16
SP - 530
EP - 536
JO - Journal of Porphyrins and Phthalocyanines
JF - Journal of Porphyrins and Phthalocyanines
IS - 5-6
ER -