464
K. Imato and Y. Ooyama
dynamics: the role of charge transfer and photostability in the selection of photosensitizers. Chem
Eur J 20:5346–5357. https://doi.org/10.1002/chem.201304202
Ashen-Garry D, Selke M (2014) Singlet oxygen generation by cyclometalated complexes and
applications. Photochem Photobiol 90:257–274. https://doi.org/10.1111/php.12211
Aubry J-M, Mandard-Cazin B, Rougee M, Bensasson RV (1995) Kinetic studies of singlet oxygen
[4+2]-cycloadditions with cyclic 1,3-dienes in 28 solvents. J Am Chem Soc 117:9159–9164.
https://doi.org/10.1021/ja00141a006
Awuah SG, You Y (2012) Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy. RSC Adv 2:11169–11183. https://doi.org/10.1039/c2ra21404k
Beverina L, Crippa M, Landenna M, Ruffo R, Salice P, Silvestri F, Versari S, Villa A, Ciaffoni
L, Collini E, Ferrante C, Bradamante S, Mari CM, Bozio R, Pagani GA (2008) Assessment
of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers:
design, synthesis, and characterization. J Am Chem Soc 130:1894–1902. https://doi.org/10.1021/
ja075933a
Bonnett R (1995) Photosensitizers of the porphyrin and phthalocyanine series for photodynamic
therapy. Chem Soc Rev 24:19–33. https://doi.org/10.1039/cs9952400019
Cakmak Y, Kolemen S, Duman S, Dede Y, Dolen Y, Kilic B, Kostereli Z, Yildirim LT, Dogan AL, Guc
D, Akkaya EU (2011) Designing excited states: theory-guided access to efficient photosensitizers
for photodynamic action. Angew Chem Int Ed 50:11937–11941. https://doi.org/10.1002/anie.201
105736
Callaghan S, Senge MO (2018) The good, the bad, and the ugly—controlling singlet oxygen through
design of photosensitizers and delivery systems for photodynamic therapy. Photochem Photobiol
Sci 17:1490–1514. https://doi.org/10.1039/C8PP00008E
Coskun A, Akkaya EU (2004) Difluorobora-s-diazaindacene dyes as highly selective dosimetric
reagents for fluoride anions. Tetrahedron Lett 45:4947–4949. https://doi.org/10.1016/j.tetlet.
2004.04.130
D˛ abrowski JM, Arnaut LG (2015) Photodynamic therapy (PDT) of cancer: from local to systemic
treatment. Photochem Photobiol Sci 14:1765–1780. https://doi.org/10.1039/C5PP00132C
DeRosa MC, Crutchley RJ (2002) Photosensitized singlet oxygen and its applications. Coord Chem
Rev 233–234:351–371. https://doi.org/10.1016/S0010-8545(02)00034-6
Detty MR, Merkel PB, Hilf R, Gibson SL, Powers SK (1990) Chalcogenapyrylium dyes as
photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting, and singlet-oxygeninduced inhibition of cytochrome c oxidase. J Med Chem 33:1108–1116. https://doi.org/10.1021/
jm00166a005
Djurovich PI, Murphy D, Thompson ME, Hernandez B, Gao R, Hunt PL, Selke M (2007) Cyclometalated iridium and platinum complexes as singlet oxygen photosensitizers: quantum yields,
quenching rates and correlation with electronic structures. Dalton Trans 298:3763–3770. https://
doi.org/10.1039/b704595f
Doria F, Manet I, Grande V, Monti S, Freccero M (2013) Water-soluble naphthalene diimides as
singlet oxygen sensitizers. J Org Chem 78:8065–8073. https://doi.org/10.1021/jo401347z
Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) The role of porphyrin chemistry in tumor imaging
and photodynamic therapy. Chem Soc Rev 40:340–362. https://doi.org/10.1039/B915149B
Fresnadillo DG, Georgiadou Y, Orellana G, Braun AM, Oliveros E (1996) Singlet-oxygen ( 1 g )
production by ruthenium(II) complexes containing polyazaheterocyclic ligands in methanol and
in water. Helv Chim Acta 79:1222–1238. https://doi.org/10.1002/hlca.19960790428
Gollnick K, Griesbeck A (1985) Singlet oxygen photooxygenation of furans: isolation and reactions
of (4+2)-cycloaddition products (unsaturated sec.-ozonides). Tetrahedron 41:2057–2068. https://
doi.org/10.1016/S0040-4020(01)96576-7
Greer A (2006) Christopher foote’s discovery of the role of singlet oxygen [ 1 O 2 ( 1 g )] in
photosensitized oxidation reactions. Acc Chem Res 39:797–804. https://doi.org/10.1021/ar0
50191g
Hammerer F, Garcia G, Chen S, Poyer F, Achelle S, Fiorini-Debuisschert C, Teulade-Fichou M-P,
Maillard P (2014) Synthesis and characterization of glycoconjugated porphyrin triphenylamine
K. Imato and Y. Ooyama
dynamics: the role of charge transfer and photostability in the selection of photosensitizers. Chem
Eur J 20:5346–5357. https://doi.org/10.1002/chem.201304202
Ashen-Garry D, Selke M (2014) Singlet oxygen generation by cyclometalated complexes and
applications. Photochem Photobiol 90:257–274. https://doi.org/10.1111/php.12211
Aubry J-M, Mandard-Cazin B, Rougee M, Bensasson RV (1995) Kinetic studies of singlet oxygen
[4+2]-cycloadditions with cyclic 1,3-dienes in 28 solvents. J Am Chem Soc 117:9159–9164.
https://doi.org/10.1021/ja00141a006
Awuah SG, You Y (2012) Boron dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy. RSC Adv 2:11169–11183. https://doi.org/10.1039/c2ra21404k
Beverina L, Crippa M, Landenna M, Ruffo R, Salice P, Silvestri F, Versari S, Villa A, Ciaffoni
L, Collini E, Ferrante C, Bradamante S, Mari CM, Bozio R, Pagani GA (2008) Assessment
of water-soluble π-extended squaraines as one- and two-photon singlet oxygen photosensitizers:
design, synthesis, and characterization. J Am Chem Soc 130:1894–1902. https://doi.org/10.1021/
ja075933a
Bonnett R (1995) Photosensitizers of the porphyrin and phthalocyanine series for photodynamic
therapy. Chem Soc Rev 24:19–33. https://doi.org/10.1039/cs9952400019
Cakmak Y, Kolemen S, Duman S, Dede Y, Dolen Y, Kilic B, Kostereli Z, Yildirim LT, Dogan AL, Guc
D, Akkaya EU (2011) Designing excited states: theory-guided access to efficient photosensitizers
for photodynamic action. Angew Chem Int Ed 50:11937–11941. https://doi.org/10.1002/anie.201
105736
Callaghan S, Senge MO (2018) The good, the bad, and the ugly—controlling singlet oxygen through
design of photosensitizers and delivery systems for photodynamic therapy. Photochem Photobiol
Sci 17:1490–1514. https://doi.org/10.1039/C8PP00008E
Coskun A, Akkaya EU (2004) Difluorobora-s-diazaindacene dyes as highly selective dosimetric
reagents for fluoride anions. Tetrahedron Lett 45:4947–4949. https://doi.org/10.1016/j.tetlet.
2004.04.130
D˛ abrowski JM, Arnaut LG (2015) Photodynamic therapy (PDT) of cancer: from local to systemic
treatment. Photochem Photobiol Sci 14:1765–1780. https://doi.org/10.1039/C5PP00132C
DeRosa MC, Crutchley RJ (2002) Photosensitized singlet oxygen and its applications. Coord Chem
Rev 233–234:351–371. https://doi.org/10.1016/S0010-8545(02)00034-6
Detty MR, Merkel PB, Hilf R, Gibson SL, Powers SK (1990) Chalcogenapyrylium dyes as
photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting, and singlet-oxygeninduced inhibition of cytochrome c oxidase. J Med Chem 33:1108–1116. https://doi.org/10.1021/
jm00166a005
Djurovich PI, Murphy D, Thompson ME, Hernandez B, Gao R, Hunt PL, Selke M (2007) Cyclometalated iridium and platinum complexes as singlet oxygen photosensitizers: quantum yields,
quenching rates and correlation with electronic structures. Dalton Trans 298:3763–3770. https://
doi.org/10.1039/b704595f
Doria F, Manet I, Grande V, Monti S, Freccero M (2013) Water-soluble naphthalene diimides as
singlet oxygen sensitizers. J Org Chem 78:8065–8073. https://doi.org/10.1021/jo401347z
Ethirajan M, Chen Y, Joshi P, Pandey RK (2011) The role of porphyrin chemistry in tumor imaging
and photodynamic therapy. Chem Soc Rev 40:340–362. https://doi.org/10.1039/B915149B
Fresnadillo DG, Georgiadou Y, Orellana G, Braun AM, Oliveros E (1996) Singlet-oxygen ( 1 g )
production by ruthenium(II) complexes containing polyazaheterocyclic ligands in methanol and
in water. Helv Chim Acta 79:1222–1238. https://doi.org/10.1002/hlca.19960790428
Gollnick K, Griesbeck A (1985) Singlet oxygen photooxygenation of furans: isolation and reactions
of (4+2)-cycloaddition products (unsaturated sec.-ozonides). Tetrahedron 41:2057–2068. https://
doi.org/10.1016/S0040-4020(01)96576-7
Greer A (2006) Christopher foote’s discovery of the role of singlet oxygen [ 1 O 2 ( 1 g )] in
photosensitized oxidation reactions. Acc Chem Res 39:797–804. https://doi.org/10.1021/ar0
50191g
Hammerer F, Garcia G, Chen S, Poyer F, Achelle S, Fiorini-Debuisschert C, Teulade-Fichou M-P,
Maillard P (2014) Synthesis and characterization of glycoconjugated porphyrin triphenylamine