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RSC Advances
Page 7 of 9
DOI: 10.1039/C6RA21575K
Journal Name
ARTICLE
9
G. Lyashenko, G. Saischek, A. Pal, R. Herbst-Irmer and N. C.
Mösch-Zanetti, Chem. Commun. 2007, , 701.
10 A. T. Gallagher, M. L. Kelty, J. G. Park, J. S. Anderson, J. A.
Mason, J. P. S. Walsh, S. L. Collinsa and T. D. Harris, Inorg.
Chem. Front. 2016, 3, 536.
11 A. Perivolaris, C. C. Stoumpos, J. Karpinsk, A. G. Ryder, J. M.
Frost, K. Mason, A. Prescimone, A. M. Z. Slawin, V. G.
Kessler, J. S. Mathieson, L. Cronin, E. K. Brechin and G. S.
Conclusion
7
In this study, the 1:2 adduct of H2TPP with DDQ has been used
for the first time as photosensitizer in the aerobic
photooxidation of cyclooctene and cyclohexene in DCE, CCl4,
acetonitrile, toluene, CDCl3. The oxidation reactions were also
conducted under fluorous biphase system (FBS) using
perfluorodecalin/DCE and perfluorodecalin/toluene mixtures.
Also, LED and metal halide lamps were used as the light
source. It was found that:
Papaefstathiou, Inorg. Chem. Front. 2014, 1, 487.
12 A. P. S. Roseiro, P. Adão, A. M. Galvão, J. C. Pessoa, A. M.
Botelho do Regob and M. F. N. N. Carvalho, Inorg. Chem.
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13 J. Long, L. Wang, X. Gao, C. Bai, H. Jianga and Y. I. Li, Chem.
Commun. 2012, 48, 12109.
14 S. Ahmad, K. Karitkey Yadav, U. Narang, S. Bhattacharya, S. J.
i. The adduct showed a remarkably increased catalytic
efficiency and oxidative stability compared to that of
the free base porphyrin, under the optimized reaction
conditions.
Singh and S. M. S. Chauhan, RSC Adv. 2016,
15 J. S. Zargari, R. Rahimi, A. Yousefi, RSC Adv. 2015,
16 C.-C. Huang, P. S. Parasuraman, H.-C. Tsai, J.-J. Jhu and T.
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17 H. Wang, Y. Fu, T.u Han, J. Wan and X. Zheng, RSC Adv. 2015,
, 33570.
18 J. Hynek, J. Rathouský, J. Demel and K. Lang, RSC Adv. 2016,
, 44279.
6, 24218.
5
, 93252.
ii. The photosensitizing ability of the adduct was found to
be essentially determined by the light absorption in
the Soret band region that is in accord with the much
higher efficiency of the blue LED lamps than that of
the red ones.
4
5
6
iii. The protonation of H2TPP was found to be efficiently
prevented by complexation to the DDQ molecules.
iv. The out-of-plane deformation of porphyrin core and
the increased polarity of the aromatic macrocycle
caused by the adduct formation between H2TPP and
DDQ led to a significant increase in its solubility in
acetonitrile. This in turn facilitated the use of
acetonitrile as a safer solvent in photooxidation
19 J. Rosenthal, T. D. Luckett, J. M. Hodgkiss and D. G. Nocera, J.
Am. Chem. Soc. 2006, 128, 6546.
20 J. Jung, K. Ohkubo, D. P. Goldberg and S. Fukuzumi, J. Phys.
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,
22 M. T. Torres, R. J. M. Nolte, A. E. Rowan and J. A. W.
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M. P. Tantak, A. Kumar, K. Akamatsu, E. Kusaka, K. Tanabe
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26 M. Hajimohammadi, N. Safari, H. Mofakham and F. Deyhimi,
Green Chem. 2011, 13, 991.
27 H. Ghafuri, Z. Movahedinia, R. Rahimi and H. R. Esmaili Zand,
reactions
catalyzed
by
porphyrin-based
photosensitizers.
v. The remarkable quencing of the flouresence of 1,3-
diphenylisobenzofuran and little effect of 1,4-
benzoquinone on the conversion of cyclooctene to
the oxidation product showed the formation of
singlet oxygen as the main photogenerated active
species under reaction conditins.
RSC Adv. 2015,
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2012, , 3257.
5, 60172.
2
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Acknowledgements
Financial Support of this work by the Institute for Advanced
Studies in Basic Sciences (IASBS) is gratefully acknowledged.
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