A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation

Eberhard J, Peuntinger K, Rath S, Neumann B, Stammler H-G, Guldi DM, Mattay J (2014)
Photochemical & Photobiological Sciences 13(2): 380-396.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
The homoleptic zinc(II) and ruthenium(II) metal complexes of bis(tridentate) 9-acridine and 10-methyl-9-acridinium-substituted terpyridines were tested for their suitability as triplet photosensitizers (PS) using the photooxidation of 1,5-dihydroxynaphthalene (DHN) to Juglone as a model reaction. Singlet oxygen (O-2 (1)Delta(g)) generation is superior or comparable to Ru(bpy)(3)(2+) for the acridine complexes, whereas the acridinium complexes are ineffective. The molecular structure of the bis(9-(5-([2,2': 6',2 ''-terpyridin]-4'-yl)-thien-2-yl)-10-methylacridinium)zinc(II) complex ([Zn(MeATT)(2)][PF6](4)) is determined by X-ray structure analysis, whereas for other complexes DFT calculations were performed for structural parameters to obtain insights into their electronic properties.
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Photochemical & Photobiological Sciences
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13
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380-396
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Eberhard J, Peuntinger K, Rath S, et al. A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation. Photochemical & Photobiological Sciences. 2014;13(2):380-396.
Eberhard, J., Peuntinger, K., Rath, S., Neumann, B., Stammler, H. - G., Guldi, D. M., & Mattay, J. (2014). A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation. Photochemical & Photobiological Sciences, 13(2), 380-396. doi:10.1039/c3pp50349f
Eberhard, J., Peuntinger, K., Rath, S., Neumann, B., Stammler, H. - G., Guldi, D. M., and Mattay, J. (2014). A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation. Photochemical & Photobiological Sciences 13, 380-396.
Eberhard, J., et al., 2014. A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation. Photochemical & Photobiological Sciences, 13(2), p 380-396.
J. Eberhard, et al., “A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation”, Photochemical & Photobiological Sciences, vol. 13, 2014, pp. 380-396.
Eberhard, J., Peuntinger, K., Rath, S., Neumann, B., Stammler, H.-G., Guldi, D.M., Mattay, J.: A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation. Photochemical & Photobiological Sciences. 13, 380-396 (2014).
Eberhard, Jens, Peuntinger, Katrin, Rath, Susann, Neumann, Beate, Stammler, Hans-Georg, Guldi, Dirk M., and Mattay, Jochen. “A study of acridine and acridinium-substituted bis(terpyridine)zinc(II) and ruthenium(II) complexes as photosensitizers for O-2 ((1)Delta(g)) generation”. Photochemical & Photobiological Sciences 13.2 (2014): 380-396.

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Dual Photoreactivity of a New Rh2(II,II) Complex for Biological Applications.
Akhimie RN, White JK, Turro C., Inorganica Chim Acta 454(), 2017
PMID: 30026633
Unprecedented strong Lewis bases--synthesis and methyl cation affinities of dimethylamino-substituted terpyridines.
Hommes P, Fischer C, Lindner C, Zipse H, Reissig HU., Angew Chem Int Ed Engl 53(29), 2014
PMID: 24895262

143 References

Daten bereitgestellt von Europe PubMed Central.

Photosensitization reactions in vitro and in vivo.
Kruft BI, Greer A., Photochem. Photobiol. 87(6), 2011
PMID: 21883245

Kavarnos, Chem. Rev. 86(), 1986
Molecular mechanisms of photosensitization.
Laustriat G., Biochimie 68(6), 1986
PMID: 3019431

Mattay, Angew. Chem. 99(), 1987

Mattay, Angew. Chem., Int. Ed. Engl. 26(), 1987
Dye-sensitized solar cells.
Hagfeldt A, Boschloo G, Sun L, Kloo L, Pettersson H., Chem. Rev. 110(11), 2010
PMID: 20831177

Hamann, Energy Environ. Sci. 1(), 2008

Grätzel, J. Photochem. Photobiol., C 4(), 2003

Zhao, RSC Adv. 1(), 2011

Singh-Rachford, Coord. Chem. Rev. 254(), 2010
From ruthenium(II) to iridium(III): 15 years of triads based on bis-terpyridine complexes.
Baranoff E, Collin JP, Flamigni L, Sauvage JP., Chem Soc Rev 33(3), 2004
PMID: 15026819

Bozic-Weber, Coord. Chem. Rev. 257(), 2013

Bignozzi, Coord. Chem. Rev. 257(), 2013

Polo, Coord. Chem. Rev. 248(), 2004
The d10 route to dye-sensitized solar cells: step-wise assembly of zinc(II) photosensitizers on TiO2 surfaces.
Bozic-Weber B, Constable EC, Hostettler N, Housecroft CE, Schmitt R, Schonhofer E., Chem. Commun. (Camb.) 48(46), 2012
PMID: 22547130

Bessho, Chem. Commun. (), 2008

Aribia, Chem. Sci. 4(), 2012
Copper(I) dye-sensitized solar cells with [Co(bpy)3](2+/3+) electrolyte.
Bozic-Weber B, Constable EC, Furer SO, Housecroft CE, Troxler LJ, Zampese JA., Chem. Commun. (Camb.) 49(65), 2013
PMID: 23843114
Porphyrin-sensitized solar cells with cobalt (II/III)-based redox electrolyte exceed 12 percent efficiency.
Yella A, Lee HW, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, Diau EW, Yeh CY, Zakeeruddin SM, Gratzel M., Science 334(6056), 2011
PMID: 22053043
Lighting porphyrins and phthalocyanines for molecular photovoltaics.
Martinez-Diaz MV, de la Torre G, Torres T., Chem. Commun. (Camb.) 46(38), 2010
PMID: 20835465

Ooyama, Eur. J. Org. Chem. (), 2009

Mishra, Angew. Chem. 121(), 2009

Mishra, Angew. Chem., Int. Ed. 48(), 2009
Triplet photosensitizers: from molecular design to applications.
Zhao J, Wu W, Sun J, Guo S., Chem Soc Rev 42(12), 2013
PMID: 23450221
Photophysics and photochemistry of photodynamic therapy: fundamental aspects.
Plaetzer K, Krammer B, Berlanda J, Berr F, Kiesslich T., Lasers Med Sci 24(2), 2008
PMID: 18247081
Photodynamic therapy of cancer. Basic principles and applications.
Juarranz A, Jaen P, Sanz-Rodriguez F, Cuevas J, Gonzalez S., Clin Transl Oncol 10(3), 2008
PMID: 18321817

Castano, Photodiagn. Photodyn. Ther. 1(), 2004
Photodynamic therapy for cancer.
Dolmans DE, Fukumura D, Jain RK., Nat. Rev. Cancer 3(5), 2003
PMID: 12724736
Photodynamic therapeutics: basic principles and clinical applications.
Sharman WM, Allen CM, van Lier JE ., Drug Discov. Today 4(11), 1999
PMID: 10529768
Singlet oxygen: there is indeed something new under the sun.
Ogilby PR., Chem Soc Rev 39(8), 2010
PMID: 20571680

Protti, Pure Appl. Chem. 79(), 2007

Albini, Green Chem. 6(), 2004

Oelgemöller, Pure Appl. Chem. 79(), 2007

Mattay, Chemie in unserer Zeit 36(), 2002

Suchard, Tetrahedron 62(), 2006

Luiz, Can. J. Chem. 74(), 1996

Schiel, Green Chem. 3(), 2001

Oelgemöller, Eur. J. Org. Chem. (), 2002

Mitchell, Green Chem. 15(), 2013

Jiménez-Hernández, Sol. Energy 80(), 2006

Villén, Appl. Catal., B 69(), 2006
Micro-photochemistry: photochemistry in microstructured reactors. The new photochemistry of the future?
Coyle EE, Oelgemoller M., Photochem. Photobiol. Sci. 7(11), 2008
PMID: 18958317

Charpentier, Chem. Eng. Technol. 35(), 2012
Efficient photosensitized oxygenations in phase contact enhanced microreactors.
Park CP, Maurya RA, Lee JH, Kim DP., Lab Chip 11(11), 2011
PMID: 21499614

DeRosa, Coord. Chem. Rev. 233–234(), 2002
Photochemical reactions as key steps in organic synthesis.
Hoffmann N., Chem. Rev. 108(3), 2008
PMID: 18302419

Greer, Tetrahedron 62(), 2006

Clennan, Tetrahedron 61(), 2005

Clennan, Tetrahedron 56(), 2000

Rosaria, Curr. Org. Chem. 9(), 2005

Prein, Angew. Chem. 108(), 1996

Prein, Angew. Chem., Int. Ed. Engl. 35(), 1996
In vitro demonstration of the heavy-atom effect for photodynamic therapy.
Gorman A, Killoran J, O'Shea C, Kenna T, Gallagher WM, O'Shea DF., J. Am. Chem. Soc. 126(34), 2004
PMID: 15327320

Adarsh, Chem.–Eur. J. 18(), 2012
Preparation of ketocoumarins as heavy atom-free triplet photosensitizers for triplet-triplet annihilation upconversion.
Huang D, Sun J, Ma L, Zhang C, Zhao J., Photochem. Photobiol. Sci. 12(5), 2013
PMID: 23467514
Photooxidation of 1,5-dihydroxynaphthalene with iridium complexes as singlet oxygen sensitizers.
Takizawa SY, Aboshi R, Murata S., Photochem. Photobiol. Sci. 10(6), 2011
PMID: 21298183

Djurovich, Dalton Trans. (), 2007
Bis-cyclometalated Ir(III) complexes as efficient singlet oxygen sensitizers.
Gao R, Ho DG, Hernandez B, Selke M, Murphy D, Djurovich PI, Thompson ME., J. Am. Chem. Soc. 124(50), 2002
PMID: 12475307

Abdel-Shafi, Helv. Chim. Acta 84(), 2001

Abdel-Shafi, Phys. Chem. Chem. Phys. 2(), 2000

Abdel-Shafi, J. Phys. Chem. A 104(), 2000

Abdel-Shafi, Dalton Trans. (), 2007

Hammarström, Coord. Chem. Rev. 254(), 2010
Bis(tridentate) ruthenium-terpyridine complexes featuring microsecond excited-state lifetimes.
Brown DG, Sanguantrakun N, Schulze B, Schubert US, Berlinguette CP., J. Am. Chem. Soc. 134(30), 2012
PMID: 22809110

Wang, J. Photochem. Photobiol., C 5(), 2004

Wu, Eur. J. Inorg. Chem. 2013(), 2013

Galletta, Chem. Commun. (), 2005

Garcia-Fresnadillo, Helv. Chim. Acta 79(), 1996
Photophysical properties and singlet oxygen production by ruthenium(II) complexes of benzo[i]dipyrido[3,2-a:2',3'-c]phenazine: spectroscopic and TD-DFT study.
Foxon SP, Alamiry MA, Walker MG, Meijer AJ, Sazanovich IV, Weinstein JA, Thomas JA., J Phys Chem A 113(46), 2009
PMID: 19791785

Benniston, Dalton Trans. (), 2004

Ding, J. Photochem. Photobiol., A 177(), 2006
Metal Ion Enhanced Charge Transfer in a Terpyridine-bis-Pyrene System.
D'Aleo A, Cecchetto E, De Cola L, Williams RM., Sensors (Basel) 9(5), 2009
PMID: 22412328

Hissler, Chem.–Eur. J. 5(), 1999

Albano, Inorg. Chim. Acta 277(), 1998
Development of singlet oxygen-responsive phosphorescent ruthenium(II) complexes.
Ye Z, Song B, Yin Y, Zhang R, Yuan J., Dalton Trans 42(40), 2013
PMID: 24022810

Wilkinson, J. Phys. Chem. Ref. Data 22(), 1993

Fukuzumi, Chem. Sci. 4(), 2013

Dolomanov, J. Appl. Crystallogr. 42(), 2009

Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 64(), 2008

Brouwer, Pure Appl. Chem. 83(), 2011

Liu, J. Am. Chem. Soc. 108(), 1986

Bergmann, J. Phys. Chem. 67(), 1963

Lee, J. Phys. Chem. B 103(), 1999
Basis set exchange: a community database for computational sciences.
Schuchardt KL, Didier BT, Elsethagen T, Sun L, Gurumoorthi V, Chase J, Li J, Windus TL., J Chem Inf Model 47(3), 2007
PMID: 17428029

Hay, J. Chem. Phys. 82(), 1985

Hay, J. Chem. Phys. 82(), 1985

Hay, J. Chem. Phys. 82(), 1985

Constable, New J. Chem. 16(), 1992

Mohamed, Spectrochim. Acta, Part A 41(), 1985
A convenient synthesis of triflate anion ionic liquids and their properties.
Ignat'ev NV, Barthen P, Kucheryna A, Willner H, Sartori P., Molecules 17(5), 2012
PMID: 22565482

Hogg, J. Chem. Soc. (), 1962

Harvey, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 60(), 2004

Dumitru, Eur. J. Inorg. Chem. 2005(), 2005
Impact of metal on the DNA photocleavage activity and cytotoxicity of ferrocenyl terpyridine 3d metal complexes.
Maity B, Gadadhar S, Goswami TK, Karande AA, Chakravarty AR., Dalton Trans 40(44), 2011
PMID: 21975663

Alcock, J. Chem. Soc., Dalton Trans. (), 2000
Synthesis, structure and luminescence properties of Cu(II), Zn(II) and Cd(II) complexes with 4'-terphenylterpyridine.
Lee YH, Kubota E, Fuyuhiro A, Kawata S, Harrowfield JM, Kim Y, Hayami S., Dalton Trans 41(35), 2012
PMID: 22859218

Wang, Inorg. Chem. Commun. 18(), 2012

Chen, J. Lumin. 126(), 2007

Kubota, Polyhedron 52(), 2013

Scudder, New J. Chem. 23(), 1999

McMurtrie, CrystEngComm 11(), 2009

McMurtrie, CrystEngComm 12(), 2010

Constable, Dalton Trans. (), 2008

Kasama, J. Phys. Chem. 85(), 1981

Holzapfel, J. Phys. Chem. C 112(), 2008
Long-lived photogenerated states of alpha-oligothiophene-acridinium dyads have triplet character.
Hu J, Xia B, Bao D, Ferreira A, Wan J, Jones G 2nd, Vullev VI., J Phys Chem A 113(13), 2009
PMID: 19267468

Jones, J. Am. Chem. Soc. 121(), 1999

Jones, J. Phys. Chem. A 101(), 1997

van, J. Phys. Chem. 100(), 1996

Jones, Chem. Phys. Lett. 229(), 1994
Triphenylamine-modified ruthenium(II) terpyridine complexes: enhancement of light absorption by conjugated bridging motifs.
Robson KC, Koivisto BD, Gordon TJ, Baumgartner T, Berlinguette CP., Inorg Chem 49(12), 2010
PMID: 20481435

Presselt, J. Phys. Chem. C 112(), 2008
A concept to tailor electron delocalization: applying QTAIM analysis to phenyl-terpyridine compounds.
Presselt M, Dietzek B, Schmitt M, Rau S, Winter A, Jager M, Schubert US, Popp J., J Phys Chem A 114(50), 2010
PMID: 21090739

Kikuchi, J. Phys. Chem. 94(), 1990

Diverdi, J. Phys. Chem. 88(), 1984

Kellmann, J. Phys. Chem. 81(), 1977
Bent structure and dynamic stereochemistry of chiral acridinium cations.
Laleu B, Herse C, Laursen BW, Bernardinelli G, Lacour J., J. Org. Chem. 68(16), 2003
PMID: 12895064
A compilation of singlet oxygen yields from biologically relevant molecules.
Redmond RW, Gamlin JN., Photochem. Photobiol. 70(4), 1999
PMID: 10546544

Tanielian, J. Phys. Chem. 99(), 1995

Tanielian, J. Photochem. 25(), 1984

Tanielian, J. Phys. Chem. 100(), 1996

Schenck, Justus Liebigs Ann. Chem. 674(), 1964

Gollnick, Pure Appl. Chem. 9(), 1964

Gollnick, Photochem. Photobiol. 43(), 1986

Foote, Tetrahedron Lett. 6(), 1965

Foote, Acc. Chem. Res. 1(), 1968

Sato, Bull. Chem. Soc. Jpn. 47(), 1974

Schieberle, J. High Resolut. Chromatogr. 10(), 1987
Photooxidation and Phototoxicity of pi-extended squaraines.
Rapozzi V, Beverina L, Salice P, Pagani GA, Camerin M, Xodo LE., J. Med. Chem. 53(5), 2010
PMID: 20131844

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