Title: High Stokes Shift Anilido‐Pyridine Boron Difluoride Dyes
Abstract: Angewandte Chemie International EditionVolume 50, Issue 51 p. 12214-12217 Communication High Stokes Shift Anilido-Pyridine Boron Difluoride Dyes† Juan F. Araneda, Juan F. Araneda Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorWarren E. Piers, Corresponding Author Warren E. Piers [email protected] Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorBelinda Heyne, Corresponding Author Belinda Heyne Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorMasood Parvez, Masood Parvez Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorRobert McDonald, Robert McDonald Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta, T6G 2G2 (Canada)Search for more papers by this author Juan F. Araneda, Juan F. Araneda Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorWarren E. Piers, Corresponding Author Warren E. Piers [email protected] Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorBelinda Heyne, Corresponding Author Belinda Heyne Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorMasood Parvez, Masood Parvez Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4 (Canada) http://www.chem.ucalgary.ca/research/groups/wpiers/Search for more papers by this authorRobert McDonald, Robert McDonald Department of Chemistry, University of Alberta, 11227 Saskatchewan Drive, Edmonton, Alberta, T6G 2G2 (Canada)Search for more papers by this author First published: 21 October 2011 https://doi.org/10.1002/anie.201105228Citations: 235 † Funding for this work was provided by the NSERC of Canada. 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 To dye for: Three related families of fluorescent dyes, rigidified by boron difluoride and based on bidentate anilido-pyridyl donor ligands, are reported (see picture). The dyes show quantum yields up to 0.75 and improved Stokes shifts of >100 nm relative to the widely employed BODIPY family of dyes. Furthermore, the new dyes are exceptionally photostable and membrane-specific. 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_201105228_sm_miscellaneous_information.pdf14 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 1 1aG. R. Whittell, M. D. Hager, U. S. Schubert, I. Manners, Nat. Mater. 2011, 10, 176; 1bA. Kaeser, A. P. H. J. Schenning, Adv. Mater. 2010, 22, 2985; 1cL. Maretti, P. S. Billone, Y. Liu, J. C. Scaiano, J. Am. Chem. Soc. 2009, 131, 13972. 2 2aM. S. T. Goncalves, Chem. Rev. 2008, 108, 190; 2bJ. M. Baumes, J. J. Gassensmith, J. Giblin, J.-J. Lee, A. G. White, W. J. Culligan, W. M. Leevy, M. Kuno, B. D. 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Crystal data for 3 b: C26H29BCl2F2N2, MW=489.22, monoclinic, P21/m, a=11.4796(5), b=6.9227(4), c=15.4393(5) Å, α=90, β=97.296(3), γ=90°, V=1217.02(10) Å3, Z=2, ρ=1.335 g cm−3, MoKα radiation, λ=0.71073 Å, T=173(2) K, 4108 measured reflection, 2965 unique, min/max transmission=0. 9650 and 0.9209 R1 (I>2σ)=0.0746, wR2=0.1721, GoF=1.057, No. of parameters=208, final difference map within +0.726 and −0.767 e Å3. CCDC 836295, 836296, 836297, 836298, 836299, 836290, 836291 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. 17K. D. Conroy, W. E. Piers, M. Parvez, J. Organomet. Chem. 2008, 693, 834. 18 18aW. Qin, M. Baruah, M. Van der Auweraer, F. C. De Schryver, N. L. Boens, J. Phys. Chem. A 2005, 109, 7371; 18bW. Qin, T. Rohand, M. Baruah, A. Stefan, M. V. der Auweraer, W. Dehaen, N. Boens, Chem. Phys. Lett. 2006, 420, 562; 18cA. Filarowski, M. 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