Title: Through‐Bond Energy Transfer Cassettes with Minimal Spectral Overlap between the Donor Emission and Acceptor Absorption: Coumarin–Rhodamine Dyads with Large Pseudo‐Stokes Shifts and Emission Shifts
Abstract: Angewandte Chemie International EditionVolume 49, Issue 2 p. 375-379 Communication Through-Bond Energy Transfer Cassettes with Minimal Spectral Overlap between the Donor Emission and Acceptor Absorption: Coumarin–Rhodamine Dyads with Large Pseudo-Stokes Shifts and Emission Shifts† Weiying Lin Prof., Weiying Lin Prof. [email protected] State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorLin Yuan, Lin Yuan State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorZengmei Cao, Zengmei Cao State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorYanming Feng, Yanming Feng State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorJizeng Song, Jizeng Song State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this author Weiying Lin Prof., Weiying Lin Prof. [email protected] State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorLin Yuan, Lin Yuan State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorZengmei Cao, Zengmei Cao State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorYanming Feng, Yanming Feng State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this authorJizeng Song, Jizeng Song State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082 (China), Fax: (+86) 731-8882-1464Search for more papers by this author First published: 28 December 2009 https://doi.org/10.1002/anie.200904515Citations: 166 † Funding was partially provided by NSFC (20872032, 20972044), NCET (08-0175), and the Key Project of the Chinese Ministry of Education (no. 108167). 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 Cassette recording: A new class of coumarin–rhodamine through-bond energy-transfer (TBET) cassettes with minimal spectral overlap between the donor emission and the acceptor absorption (see picture) show large pseudo-Stokes shifts (up to 230 nm) and emission shifts (up to 170 nm). The utility of this TBET platform for TBET-based probe development was demonstrated by a new ratiometric fluorescence pH probe. Supporting Information Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200904515_sm_miscellaneous_information.pdf1.1 MB miscellaneous_information 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 some reviews and examples, see: 1aT. Terai, T. Nagano, Curr. Opin. Chem. Biol. 2008, 12, 515–521; 1bA. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, T. E. Rice, Chem. Rev. 1997, 97, 1515–1566; 1cE. M. Nolan, S. J. Lippard, Chem. Rev. 2008, 108, 3443–3480; 1dW. Lin, L. Yuan, Z. Cao, Y. Feng, L. Long, Chem. Eur. J. 2009, 15, 5096–5103; 1eS. Mizukami, R. Takikawa, F. Sugihara, M. Shirakawa, K. Kikuchi, Angew. Chem. 2009, 121, 3695–3697; Angew. Chem. Int. Ed. 2009, 48, 3641–3643; 1fD. W. Domaille, E. L Que, C. J Chang, Nat. Chem. Biol. 2008, 4, 168–175; 1gL. Marbella, B. Serli-Mitasev, P. Basu, Angew. Chem. 2009, 121, 4056–4058; Angew. Chem. Int. Ed. 2009, 48, 3996–3998; 1hA. L. Garner, C. M. St Croix, B. R. Pitt, G. D. Leikauf, S. Ando, K. Koide, Nat. Chem. 2009, 1, 316–321; 1iT. Schwarze, H. Müller, C. Dosche, T. Klamroth, Wu. Mickler, A. Kelling, H.-G. Löhmannsröben, P. Saalfrank, H.-J. Holdt, Angew. Chem. 2007, 119, 1701–1704; Angew. Chem. Int. Ed. 2007, 46, 1671–1674; 1jM. Taki, M. Desaki, A. Ojida, S. Iyoshi, T. Hirayama, I. Hamachi, Y. Yamamoto, J. Am. Chem. Soc. 2008, 130, 12564–12565; 1kS. Malashikhin, N. S. Finney, J. Am. Chem. Soc. 2008, 130, 12846–12847; 1lA. Palma, M. Tasior, D. O. Frimannsson, T. T. Vu, R. Méallet-Renault, D. F. O’Shea, Org. Lett. 2009, 11, 3638–3641; 1mR. Guliyev, A. Coskun, E. U. Akkaya, J. Am. Chem. Soc. 2009, 131, 9007–9013. 2For some reviews and examples, see: 2aM. S. T. Gonçalves, Chem. Rev. 2009, 109, 190–212; 2bU. Resch-Genger, M. Grabolle, S. Cavaliere-Jaricot, R. Nitschke, T. Nann, Nat. Methods 2008, 5, 763–775; 2cA. Waggoner, Curr. Opin. Chem. Biol. 2006, 10, 62–66; 2dM. J. Hangauer, C. R. Bertozzi, Angew. Chem. 2008, 120, 2428–2431; Angew. Chem. Int. Ed. 2008, 47, 2394–2397. 3For some reviews and examples, see: 3aS. D. Straight, P. A. Liddell, Y. Terazono, T. A. Moore, A. L. Moore, D. Gust, Adv. Funct. Mater. 2007, 17, 777–785; 3bA. Coskun, E. Deniz, E. U. Akkaya, Org. Lett. 2005, 7, 5187–5189; 3cU. Pischel, Angew. Chem. 2007, 119, 4100–4115; Angew. Chem. Int. Ed. 2007, 46, 4026–4040; 3dK. Szaciłowski, Chem. Rev. 2008, 108, 3481–3548; 3eS. Kou, H. N. Lee, D. van Noort, K. M. K. Swamy, S. H. Kim, J. H. Soh, K.-M. Lee, S.-W. Nam, J. Yoon, S. Park, Angew. Chem. 2008, 120, 886–890; Angew. Chem. Int. Ed. 2008, 47, 872–876; 3fK. Rurack, C. Trieflinger, A. Kovalchuck, J. Daub, Chem. Eur. J. 2007, 13, 8998–9003; 3gL. Mu, W. Shi, G. She, J. C. Chang, S.-T. Lee, Angew. Chem. 2009, 121, 3521–3524; Angew. Chem. Int. Ed. 2009, 48, 3469–3472. 4For some reviews and examples, see: 4aB. Li, J. Li, Y. Fu, Z. Bo, J. Am. Chem. Soc. 2004, 126, 3430–3431; 4bB. Domercq, C. Grasso, J. Maldonado, M. Halik, S. Barlow, S. R. Marder, B. Kippelen, J. Phys. Chem. B 2004, 108, 8647–8651; 4cZ. H. Li, M. S. Wong, Org. lett. 2006, 8, 1499–1502; 4dC.-T Chen, Chem. Mater. 2004, 16, 4389–4400. 5For some examples, see: 5aT. Ishi-i, K. Murakami, Y. Imai, S. Mataka, Org. Lett. 2005, 7, 3175–3178; 5bK. Becker, J. M. Lupton, J. Am. Chem. Soc. 2006, 128, 6468–6479; 5cD. S. Tyson, F. N. Castellano, Inorg. Chem. 1999, 38, 4382–4383; 5dS. Zrig, P. Remy, B. Andrioletti, E. Rose, I. Asselberghs, K. Clays, J. Org. Chem. 2008, 73, 1563- 1566; 5eX. Zhang, Z.-K. Chen, K. P. Loh, J. Am. Chem. Soc. 2009, 131, 7210–7211; 5fA. Ajayaghosh, V. K. Praveen, C. Vijayakumar, S. J. George, Angew. Chem. 2007, 119, 6376–6381; Angew. Chem. Int. Ed. 2007, 46, 6260–6265. 6 6aL. Tolosa, K. Nowaczyk, J. Lakowicz, An Introduction to Laser Spectroscopy, 2nd ed., Kluwer, New York, 2002; 6bX. Zhang, Y. Xiao, X. Qian, Angew. Chem. 2008, 120, 8145–8149; Angew. Chem. Int. Ed. 2008, 47, 8025–8029. 7 7aA. Burghart, L. H. Thoresen, J. Chen, K. Burgess, F. Bergström, L. B.-Å. Johansson, Chem. Commun. 2000, 2203–2204; 7bA. Coskun, E. U. Akkaya, J. Am. Chem. Soc. 2006, 128, 14474–14475. 8 8aM. Suresh, S. Mishra, S. K. Mishra, E. Suresh, A. K. Mandal, A. Shrivastav, A. Das, Org. Lett. 2009, 11, 2740–2743; 8bM. H. Lee, H. J. Kim, S. Yoon, N. Park, J. S. Kim, Org. Lett. 2008, 10, 213–216; 8cJ. Yang, H. Chen, I. R. Vlahov, J.-X. Cheng, P. S. Low, Proc. Natl. Acad. Sci. USA 2006, 103, 13872–13877; 8dA. E. Albers, V. S. Okreglak, C. J. Chang, J. Am. Chem. Soc. 2006, 128, 9640–9641; 8eT. Komatsu, K. Kikuchi, H. Takakusa, K. Hanaoka, T. Ueno, M. Kamiya, Y. Urano, T. Nagano, J. Am. Chem. Soc. 2006, 128, 15946–15947. 9 9aG.-S. Jiao, L. H. Thoresen, K. Burgess, J. Am. Chem. Soc. 2003, 125, 14668–14669; 9bR. Bandichhor, A. D. Petrescu, A. Vespa, A. B. Kier, F. Schroeder, K. Burgess, J. Am. Chem. Soc. 2006, 128, 10688–10689; 9cJ. Han, J. Jose, E. Mei, K. Burgess, Angew. Chem. 2007, 119, 1714–1717; Angew. Chem. Int. Ed. 2007, 46, 1684–1687. 10J. R. Lakowicz, Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer/Plenum, New York, 1999. 11E. Kimura, T. Koike, Chem. Soc. Rev. 1998, 27, 179–184. 12The term “cassette” refers to a multifluorophore system in which the individual chromophores behave independently in the ground state but can interact in the excited state because of a spacer between chromophores that prevents full conjugation. We thank an anonymous reviewer for providing the definition of cassette. 13According to Ref. [9b], the energy transfer efficiency of TBET cassettes was calculated from 100 %×[(fluorescence of donor)−(fluorescence of donor in cassette)/(fluorescence of donor)]. 14 14aJ. Su, H. Tian, K. Chen, Dyes Pigm. 1996, 31, 69–77; 14bH. Tian, Y. Tang, K. Chen, Dyes Pigm. 1994, 26 159–165; 14cL. G. Lee, S. L. Spurgeon, B. U. S. Rosenblum, Patent 7,169,939, 2007; 14dL. G. Lee, S. L. Spurgeon, C. R. Heiner, S. C. Benson, B. B. Rosenblum, S. M. Menchen, R. J. Graham, A. Constantinescu, K. G. Upadhya, J. M. Cassel, Nucleic Acids Res. 1997, 25, 2816–2822. 15D. Magde, G. E. Rojas, P. Seybold, Photochem. Photobiol. 1999, 70, 737–744. 16M. Adamczyk, M. Cornwell, J. Huff, S. Rege, T. V. S. Rao, Bioorg. Med. Chem. Lett. 1997, 7, 1985–1988. Citing Literature Volume49, Issue2January 8, 2010Pages 375-379 ReferencesRelatedInformation
Publication Year: 2009
Publication Date: 2009-12-28
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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