Preparation of ketocoumarins as heavy atom-free triplet photosensitizers for triplet—triplet annihilation upconversio

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作者
Dandan Huang
Jifu Sun
Lihua Ma
Caishun Zhang
Jianzhang Zhao
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[1] Dalian University of Technology,State Key Laboratory of Fine Chemicals, School of Chemical Engineering
来源
Photochemical & Photobiological Sciences | 2013年 / 12卷
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摘要
A series of ketocoumarin compounds were prepared as heavy atom-free triplet photosensitizers. The photophysical properties of the compounds were studied with steady state and time-resolved spectroscopy. The compounds show absorption in the visible spectral region (molar absorption coefficients are up to ε = 136 000 M−1 cm−1 at 448 nm) and long-lived triplet excited states (τT = 199.7 μs) upon visible light photoexcitation. The compounds were used as triplet photosensitizers for singlet oxygen (1O2)-mediated photooxidation of 1,5-dihydroxylnaphthalene (DHN) to produce juglone. 1O2 quantum yields of these compounds were determined in the range of 0.28–0.48. The ketocoumarins were also used as triplet photosensitizers for triplet—triplet annihilation (TTA) upconversion, and upconversion quantum yields up to 11.3% were observed. The results are useful for preparation of heavy atom-free triplet photosensitizers and for their application in photocatalysis and TTA upconversion.
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页码:872 / 882
页数:10
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  • [1] Yasu Y(2012)Sunlight-driven synthesis of γ-diketones Chem. Commun. 48 5355-5357
  • [2] Koike T(2011) oxidative coupling of enamines with silyl enol ethers catalyzed by [Ru(bpy) Chem. Commun. 47 12709-12711
  • [3] Akita M(2012)] Chem. Soc. Rev. 41 7687-7697
  • [4] Rueping M(2004)Visible-light photoredox catalyzed oxidative Strecker reaction J. Am. Chem. Soc. 126 10619-10631
  • [5] Zhu S(2010)Photoredox functionalization of C–H bonds adjacent to a nitrogen atom Photochem. Photobiol. Sci. 9 1589-1596
  • [6] Koenigs R M(2009) demonstration of the heavy-atom effect for photodynamic therapy Photochem. Photobiol. 85 1053-1074
  • [7] Shi L(2011)Light relief: photochemistry and medicine Angew. Chem. Int. Ed. 50 11937-11941
  • [8] Xia W(2012)Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy J. Am. Chem. Soc. 134 754-757
  • [9] Gorman A(2011)Designing excited states: theory-guided access to efficient photosensitizers for photodynamic action Chem.–Eur. J. 17 15027-15031
  • [10] Killoran J(2008)Organometallic cages as vehicles for intracellular release of photosensitizers J. Mater. Chem. 18 4762-4768