Exciplex-like emission from a closely-spaced, orthogonally-sited anthracenyl-boron dipyrromethene (Bodipy) molecular dyad

Photochemical and Photobiological Sciences

Volumn 9, Issue 7, 2010, Pages 1009-1017

  Benniston, Andrew C ^a   Harriman, Anthony ^a   Whittle, Victoria L ^a   Zelzer, Mischa ^a   Harrington, Ross W ^a   Clegg, William ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77954186597     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c0pp00039f     Document Type: Article

References (25)

1. M. Gordon, and, W. R. Ware, ed., The Exciplex, Academic Press, New York, 1975
2. A. Weller Electron transfer and complex formation in the excited state Pure Appl. Chem. 1968 16 115
3. S. L. Mattes S. Farid Exciplexes and electron transfer reactions Science 1984 226 917
4. J. Hinatu H. Masuhura N. Mataga Y. Sakata S. Misumi Absorption spectra of inter- and intramolecular exciplex systems of pyrene and N,N-dimethylaniline in alcoholic solutions Bull. Chem. Soc. Jpn. 1978 51 1032
5. J. W. Verhoeven T. Scherer R. J. Willemse Solvent effects on the structure of fluorescent exciplexes in rigidly-, flexibly-, and non-bridged donor-acceptor systems Pure Appl. Chem. 1993 65 1717
6. A. C. Benniston G. Copley A. Harriman D. B. Rewinska R. W. Harrington W. Clegg A donor-acceptor molecular dyad showing multiple electronic energy-transfer processes in crystalline and amorphous states J. Am. Chem. Soc. 2008 130 7174
7. G. Ulrich R. Ziessel A. Harriman The chemistry of fluorescent bodipy dyes: Versitility unsurpassed Angew. Chem., Int. Ed. 2008 47 1184
8. D. D. Perrin and W. L. F. Armerego, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford, 1988
9. R. Ziessel L. Bonardi P. Retailleau G. Ulrich Isocyanate-, isothiocyanate-, and thiourea-substituted boron dipyrromethene dyes as fluorescent probes J. Org. Chem. 2006 71 3093
10. A. C. Benniston A. Harriman V. L. Whittle M. Zelzer Molecular rotors based on the boron dipyrromethene fluorophore Eur. J. Org. Chem. 2010 523
11. A. C. Benniston G. Copley Lighting the way ahead with boron dipyrromethene (Bodipy) dyes Phys. Chem. Chem. Phys. 2009 11 4124
12. H. Tachikawa L. R. Faulkner Energy transfer from exciplexes to hydrocarbon quenchers in polar solvents J. Am. Chem. Soc. 1976 98 5569
13. J.-Y. Xue V. D. Parker Aryl proton transfer reactions of 9-arylanthracene and 9-substituted anthracene radical cations with 2,6-di-tert-butylpyridine J. Org. Chem. 1994 59 6564
14. P. Toele H. Zhang C. Triflinger J. Daub M. Glasbeek Femtosecond fluorescence upconversion study of a boron dipyrromethene dye in solution Chem. Phys. Lett. 2003 368 66
15. C.-W. Wan A. Burghart J. Chen F. Bergström B.-Å. Johansson M. F. Wolford T. G. Kim M. R. Topp R. M. Hochstrasser K. Burgess Anthracene BODIPY cassettes: Synthesis and energy transfer Chem.-Eur. J. 2003 9 4430
16. M. A. H. Alamiry A. C. Benniston G. Copley K. J. Elliott A. Harriman B. Stewart Y.-G. Zhi A molecular rotor based on an unhindered boron dipyrromethene (Bodipy) dye Chem. Mater. 2008 20 4024
17. M. K. Kuimova G. Yahioglu J. A. Levitt K. Suhling Molecular rotor measures viscosity in live cells via fluorescence lifetime imaging J. Am. Chem. Soc. 2008 130 6672
18. J. S. Jaworski P. Leszczyński Dynamic solvent effects on the rates of homogeneous electron transfer to chlorobenzene J. Chem. Soc., Faraday Trans. 1997 93 3529
19. T. Rohand L. Lycoops S. Smout E. Braeken M. Sliwa M. Van de Auweraer E. Dehaen W. M. De Borggraeve N. Boens Photophysics of 3,5-diphenoxy substituted BODIPY dyes in solution Photochem. Photobiol. Sci. 2007 6 1061
20. S. J. Strickler R. A. Berg The relationship between absorption intensity and fluorescence lifetime of molecules J. Chem. Phys. 1962 37 814
21. F. D. Lewis B. E. Chen Solvent-dependent behaviour of phenanthrene-amine intramolecular exciplexes J. Phys. Chem. 1994 98 10591
22. M. Bixon J. Jortner J. W. Verhoeven Lifetimes for radiative charge recombination in donor-acceptor molecules J. Am. Chem. Soc. 1994 116 7349
23. D. G. Cameron S. C. His J. Umemura H. H. Mantsch Solvent induced frequency shifts of the C-H stretching bands of n-octane. A Fourier transform infrared study Can. J. Chem. 1981 59 1357
24. I. Sunahara Y. Urano H. Kojima T. Nagano Design and synthesis of a library of BODIPY-based environmental polarity sensors utliizing photoinduced electron transfer controlled fluorescence ON/OFF switching J. Am. Chem. Soc. 2007 129 5597
25. A. C. Benniston G. Copley H. Lemmetyinen N. V. Tkachenko Exciplex formation and excited state deactivation of difluorborondipyrromethene (Bodipy) dyads ChemPhysChem 2010 11 1684