Title: Toward Fluorescent Memories with Nondestructive Readout: Photoswitching of Fluorescence by Intramolecular Electron Transfer in a Diaryl Ethene‐Perylene Bisimide Photochromic System
Abstract: Angewandte Chemie International EditionVolume 47, Issue 35 p. 6616-6619 Communication Toward Fluorescent Memories with Nondestructive Readout: Photoswitching of Fluorescence by Intramolecular Electron Transfer in a Diaryl Ethene-Perylene Bisimide Photochromic System† Martin Berberich, Martin Berberich Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this authorAna-Maria Krause, Ana-Maria Krause Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this authorMichele Orlandi, Michele Orlandi Università di Ferrara, Dipartimento di Chimica, 44100 Ferrara (Italy), Fax: (+39) 0532-240-709Search for more papers by this authorFranco Scandola Prof. Dr., Franco Scandola Prof. Dr. [email protected] Università di Ferrara, Dipartimento di Chimica, 44100 Ferrara (Italy), Fax: (+39) 0532-240-709Search for more papers by this authorFrank Würthner Prof. Dr., Frank Würthner Prof. Dr. [email protected] Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this author Martin Berberich, Martin Berberich Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this authorAna-Maria Krause, Ana-Maria Krause Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this authorMichele Orlandi, Michele Orlandi Università di Ferrara, Dipartimento di Chimica, 44100 Ferrara (Italy), Fax: (+39) 0532-240-709Search for more papers by this authorFranco Scandola Prof. Dr., Franco Scandola Prof. Dr. [email protected] Università di Ferrara, Dipartimento di Chimica, 44100 Ferrara (Italy), Fax: (+39) 0532-240-709Search for more papers by this authorFrank Würthner Prof. Dr., Frank Würthner Prof. Dr. [email protected] Universität Würzburg, Institut für Organische Chemie, Am Hubland, 97074 Würzburg (Germany), Fax: (+49) 931-888-4756Search for more papers by this author First published: 11 August 2008 https://doi.org/10.1002/anie.200802007Citations: 171 † Financial support from MUR (PRIN 2006 030320) is gratefully acknowledged. We thank S. Carli for preliminary synthetic work and C. Chiorboli for help with the femtosecond studies. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Flicking a switch: Photoinduced electron transfer (PET) occurs between the perylene and the closed (but not the open) form of the diarylethene unit in a prototype optical memory system based on a photochromic diarylethene-perylene bisimide dyad (see picture). This allows three different wavelengths to be used for the read, write, and erase steps without destructive readout occurring by photochromic cycloreversion. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z802007_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1For reviews see: 1aM. Irie, T. Mrozek, J. Daub, A. Ajayaghosh, Y. Yokoyama in Molecular Switches (Ed.: ), Wiley-VCH, Weinheim, 2001, pp. 37–121; 1b Photochromism: Molecules and Systems (Eds.: ), Elsevier, New York, 1990; 1c Molecular Devices and Machines: A journey into the Nano World (Eds.: ), Wiley-VCH, Weinheim, 2003; 1dB. L. Feringa, J. Org. Chem. 2007, 72, 6635–6652. 2J. Fölling, V. Belov, R. Kunetsky, R. Medda, A. Schönle, A. Egner, C. Eggeling, M. Bossi, S. W. Hell, Angew. Chem. 2007, 119, 6382–6386; Angew. Chem. Int. Ed. 2007, 46, 6266–6270. 3 3aM. Irie, Chem. Rev. 2000, 100, 1685–1716; 3bH. Tian, S. J. Yang, Chem. Soc. Rev. 2004, 33, 85–97; 3cH. Tian, S. Wang, Chem. Commun. 2007, 781–792. 4 4aM. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759–760; 4bT. Fukaminato, T. Sasaki, T. Kawai, N. Tamai, M. Irie, J. Am. Chem. Soc. 2004, 126, 14843–14849; 4cT. A. Golovkova, D. V. Kozlov, D. C. Neckers, J. Org. Chem. 2005, 70, 5545–5549; 4dG. Jiang, S. Wang, W. Yuan, L. Jiang, Y. Song, H. Tian, D. Zhu, Chem. Mater. 2006, 18, 235–237; 4eJ. H. Hurenkamp, J. J. D. de Jong, W. R. Browne, J. H. van Esch, B. L. Feringa, Org. Biomol. Chem. 2008, 6, 1268–1277. 5 5a Supramolecular Photochemistry (Eds. ), Ellis Horwood, New York, 1991; 5b Electron Transfer in Chemistry (Ed.: ), Wiley-VCH, Weinheim, 2001; 5c Fundamentals of Photoinduced Electron Transfer (Ed. ), VCH Publishers, New York, 1993; 5dN. Mataga, H. Chosrowjan, S. Taniguchi, J. Photochem. Photobiol. C 2005, 6, 37–79; 5eD. M. Guldi, Chem. Soc. Rev. 2002, 31, 22–36; 5fJ. M. Endtner, F. Effenberger, A. Hartschuh, H. Port, J. Am. Chem. Soc. 2000, 122, 3037–3046. 6 6aA. J. Myles, N. R. Branda, J. Am. Chem. Soc. 2001, 123, 177–178; 6bY. Terazono, G. Kodis, J. Andréasson, G. Jeong, A. Brune, T. Hartmann, H. Dürr, T. A. Moore, A. L. Moore, D. Gust, J. Phys. Chem. B 2004, 108, 1812–1814; 6cF. M. Raymo, M. Tomasulo, Chem. Soc. Rev. 2005, 34, 327–336. 7Electrochemically induced ring opening/closure has been reported to occur upon oxidation of diaryl ethenes.[8] In principle, therefore, destructive readout could not be ruled out with this type of electron-transfer quenching. 8 8aT. Koshido, T. Kawai, K. Yoshino, J. Phys. Chem. 1995, 99, 6110–6114; 8bA. Peters, N. R. Branda, J. Am. Chem. Soc. 2003, 125, 3404–3405; 8cA. Peters, N. R. Branda, Chem. Commun. 2003, 954–955; 8dB. Gorodetsky, H. D. Samachetty, R. L. Donkers, M. S. Workentin, N. R. Branda, Angew. Chem. 2004, 116, 2872–2875; Angew. Chem. Int. Ed. 2004, 43, 2812–2815; 8eS. Fraysse, C. Coudret, J. P. Launay, Eur. J. Inorg. Chem. 2000, 1581–1590; 8fX. H. Zhou, F. S. Zhang, P. Yuan, F. Sun, S. Z. Pu, F. Q. Zhao, C. H. Tung, Chem. Lett. 2004, 33, 1006–1007; 8gW. R. Browne, J. J. D. de Jong, T. Kudernac, M. Walko, L. N. Lucas, K. Uchida, J. H. van Esch, B. L. Feringa, Chem. Eur. J. 2005, 11, 6414–6429; 8hW. R. Browne, J. J. D. de Jong, T. Kudernac, M. Walko, L. N. Lucas, K. Uchida, J. H. van Esch, B. L. Feringa, Chem. Eur. J. 2005, 11, 6430–6441; 8iG. Guirado, C. Coudret, M. Hliwa, J. P. Launay, J. Phys. Chem. B 2005, 109, 17445–17459; 8jY. Moriyama, K. Matsuda, N. Tanifuji, S. Irie, M. Irie, Org. Lett. 2005, 7, 3315–3318. 9The requirement that forbids energy transfer from the excited dye to both forms of the diaryl ethene implies, on the other hand, that the reverse energy-transfer processes are thermodynamically allowed. In practice, however, energy transfer to the dye is not expected to compete effectively with the ultrafast (a few ps) ring closure/opening processes of the diaryl ethene excited state. 10The concept has recently been suggested by Y. Odo, T. Fukaminato, M. Irie, Chem. Lett. 2007, 36, 240–241, and by us: M. Berberich, Masters Thesis, University of Würzburg, Würzburg (Germany), 2007. 11F. Würthner, Chem. Commun. 2004, 1564–1579. 12The quantum yield for the photocyclization of the open form PBI–DAE 1 o at 350 nm in dichloromethane is estimated to be 0.017. 13A. Z. Weller, Z. Phys. Chem. 1982, 133, 93–98. 14An approximate value for the driving force, calculated with average molecular radii of ca. 7 Å in the Rehm–Weller equation, is ca. −0.15 eV. 15 15aA. S. Lukas, Y. Zhao, S. E. Miller, M. R. Wasielewski, J. Phys. Chem. B 2002, 106, 1299–1306; 15bM. J. Ahrens, M. J. Tauber, M. R. Wasielewski, J. Org. Chem. 2006, 71, 2107–2114. Citing Literature Volume47, Issue35August 18, 2008Pages 6616-6619 ReferencesRelatedInformation
Publication Year: 2008
Publication Date: 2008-08-05
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
Access and Citation
Cited By Count: 181
AI Researcher Chatbot
Get quick answers to your questions about the article from our AI researcher chatbot