Designing Excited States: Theory-Guided Access to Efficient Photosensitizers for Photodynamic Action†
Yusuf Cakmak
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorSafacan Kolemen
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorSelin Duman
Department of Chemistry, Gazi University, Ankara, 06500 (Turkey)
Search for more papers by this authorDr. Yavuz Dede
Department of Chemistry, Gazi University, Ankara, 06500 (Turkey)
Search for more papers by this authorYusuf Dolen
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorBilal Kilic
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorZiya Kostereli
Department of Chemistry, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorProf. Dr. Leyla Tatar Yildirim
Department of Engineering Physics, Hacettepe University, Ankara, 06800 (Turkey)
Search for more papers by this authorProf. Dr. A. Lale Dogan
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorProf. Dr. Dicle Guc
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorCorresponding Author
Prof. Dr. Engin U. Akkaya
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Department of Chemistry, Bilkent University, Ankara, 06800 (Turkey)
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)Search for more papers by this authorYusuf Cakmak
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorSafacan Kolemen
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorSelin Duman
Department of Chemistry, Gazi University, Ankara, 06500 (Turkey)
Search for more papers by this authorDr. Yavuz Dede
Department of Chemistry, Gazi University, Ankara, 06500 (Turkey)
Search for more papers by this authorYusuf Dolen
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorBilal Kilic
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorZiya Kostereli
Department of Chemistry, Bilkent University, Ankara, 06800 (Turkey)
Search for more papers by this authorProf. Dr. Leyla Tatar Yildirim
Department of Engineering Physics, Hacettepe University, Ankara, 06800 (Turkey)
Search for more papers by this authorProf. Dr. A. Lale Dogan
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorProf. Dr. Dicle Guc
Department of Basic Oncology, Oncology Institute, Hacettepe University, Ankara, 06100 (Turkey)
Search for more papers by this authorCorresponding Author
Prof. Dr. Engin U. Akkaya
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)
Department of Chemistry, Bilkent University, Ankara, 06800 (Turkey)
UNAM-Institute of Materials Science and Nanotechnology, Bilkent University, Ankara, 06800 (Turkey)Search for more papers by this authorWe are grateful for funding by the National Boron Research Institute (BOREN), the Turkish Academy of Sciences (TUBA), and State Planning Organization (DPT). Additional funding from TUBITAK (110T076 and 110T647) and GU-BAP is gratefully acknowledged. S.D. thanks TUBITAK for a scholarship.
Graphical Abstract
Das rechnergestützte Design tetraradikalischer S1-Zustände wurde experimentell durch Synthese und anschließende Charakterisierung einschließlich Phosphoreszenzmessungen, Gebrauch von Einfangmolekülen und Zellkultur-Untersuchungen bestätigt. Dies führte zu einer Reihe orthogonaler Bodipy-Chromophor-Dimere mit bemerkenswerten Singulett-Sauerstoff-Effizienzen (siehe Bild). Ein neuer Weg für die rationale Entwicklung effizienter Photosensibilisatoren wird somit vorgestellt.
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References
- 1S. B. Brown, E. A. Brown, I. Walker, Lancet Oncol. 2004, 5, 497–508.
- 2J. F. Lovell, T. W. B. Liu, J. Chen, G. Zheng, Chem. Rev. 2010, 110, 2839–2857.
- 3R. Bonnett, Chem. Soc. Rev. 1995, 24, 19–33.
- 4A. P. Castano, P. Mroz, M. R. Hamblin, Nat. Rev. Cancer 2006, 6, 535–545.
- 5N. Adarsh, R. R. Avirah, D. Ramaiah, Org. Lett. 2010, 12, 5720–5723.
- 6T. Yogo, Y. Urano, Y. Ishitsuka, F. Maniwa, T. Nagano, J. Am. Chem. Soc. 2005, 127, 12162–12163.
- 7S. H. Lim, C. Thivierge, P. Nowak-Sliwinska, J. Han, H. van den Bergh, G. Wagnieres, K. Burgess, H. B. Lee, J. Med. Chem. 2010, 53, 2865–2874.
- 8L. Salem, C. Rowland, Angew. Chem. 1972, 84, 86–106;
10.1002/ange.19720840303 Google ScholarAngew. Chem. Int. Ed. Engl. 1972, 11, 92–111.
- 9L. Salem in Electrons in chemical reactions: First principles, Wiley, New York, 1982.
- 10J. Michl, J. Am. Chem. Soc. 1996, 118, 3568–3579.
- 11R. Ziessel, G. Ulrich, A. Harriman, New J. Chem. 2007, 31, 496–501.
- 12R. Ziessel, A. Harriman, Chem. Commun. 2011, 47, 611–631.
- 13O. A. Bozdemir, R. Guliyev, O. Buyukcakir, S. Selcuk, S. Kolemen, G. Gulseren, T. Nalbantoglu, H. Boyaci, E. U. Akkaya, J. Am. Chem. Soc. 2010, 132, 8029–8036.
- 14S. Kolemen, O. A. Bozdemir, Y. Cakmak, G. Barin, S. Ertan-Ela, M. Marszalek, J. H. Yum, S. M. Zakeeruddin, M. K. Nazeeruddin, M. Grätzel, E. U. Akkaya, Chem. Sci. 2011, 2, 949–954.
- 15O. A. Bozdemir, Y. Cakmak, F. Sozmen, T. Ozdemir, A. Siemiarczuk, E. U. Akkaya, Chem. Eur. J. 2010, 16, 6346–6351.
- 16I. Yildiz, S. Impellizzeri, E. Deniz, B. McCaughan, J. F. Callan, F. M. Raymo, J. Am. Chem. Soc. 2011, 133, 871–879.
- 17H. J. Kim, S. H. Kim, J. H. Kim, E-H. Lee, K-W. Kim, J. S. Kim, Bull. Korean Chem. Soc. 2008, 29, 1831–1834.
- 18A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891–4932.
- 19G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. 2008, 120, 1202–1219;
10.1002/ange.200702070 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 1184–1201.
- 20Y. Cakmak, E. U. Akkaya, Org. Lett. 2009, 11, 85–88.
- 21O. Buyukcakir, O. A. Bozdemir, S. Kolemen, S. Erbas, E. U. Akkaya, Org. Lett. 2009, 11, 4644–4647.
- 22G. Ulrich, C. Goze, M. Guardigli, A. Roda, R. Ziessel, Angew. Chem. 2005, 117, 3760–3764;
10.1002/ange.200500808 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 3694–3698.
- 23X. Qi, S. K. Kim, E. J. Jun, L. Xu, S.-J. Kim, J. Yoon, Bull. Korean Chem. Soc. 2007, 28, 2231–2234.
- 24J. Killoran, L. Allen, J. F. Gallapher, W. M. Gallapher, D. F. O’Shea, Chem. Commun. 2002, 1862–1863.
- 25S. O. McDonnell, M. J. Hall, L. T. Allen, A. Byrne, W. M. Gallagher, D. F. O’Shea, J. Am. Chem. Soc. 2005, 127, 16360–16361.
- 26S. Atilgan, Z. Ekmekci, A. L. Dogan, D. Guc, E. U. Akkaya, Chem. Commun. 2006, 4398–4400.
- 27S. Ozlem, E. U. Akkaya, J. Am. Chem. Soc. 2009, 131, 48–49.
- 28S. Erbas, A. Gorgulu, M. Kocakusakogullari, E. U. Akkaya, Chem. Commun. 2009, 4956–4958.
- 29B. Ventura, G. Marconi, M. Broring, R. Kruger, L. Flamigni, New J. Chem. 2009, 33, 428–438.
- 30L. Jiao, C. Yu, J. Li, Z. Wang, M. Wu, E. Hao, J. Org. Chem. 2009, 74, 7525–7528.
- 31K. Krumova, G. Cosa, J. Am. Chem. Soc. 2010, 132, 17560–17569.
- 32M. Mirenda, C. A. Strassert, L. E. Dicelio, E. San Roman, ACS Appl. Mater. Interfaces 2010, 2, 1556–1560.
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