Synthesis and photophysical properties of covalently linked boron dipyrromethene dyads

Dyes and Pigments

Volumn 94, Issue 1, 2012, Pages 66-73

  Khan, Tamanna K ^a   Shaikh, Mushtaque S ^b   Ravikanth, M ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b BOMBAY COLLEGE OF PHARMACY   (India)

Author keywords

Boron dipyrromethene dyads; DFT; Easier reductions; Energy transfer; Meso furyl boron dipyrromethenes; TDDFT

Indexed keywords

BORON DIPYRROMETHENE; COUPLING REACTION; DFT; DFT STUDY; EXPERIMENTAL OBSERVATION; LOWER ENERGIES; MESO-FURYL BORON DIPYRROMETHENES; NMR TECHNIQUES; PHOTOPHYSICAL PROPERTIES; RADIATIVE TRANSITIONS; RESTRICTED ROTATIONS; SINGLET STATE; STEADY STATE FLUORESCENCES; TDDFT; TIME-RESOLVED FLUORESCENCE;

BORON; BORON COMPOUNDS; ENERGY TRANSFER; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL);

FLUORESCENCE;

EID: 84055187718     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.12.002     Document Type: Article

References (34)

1. X. Hu, A. Damjanovic, T. Ritz, and K. Schulten Architecture and mechanism of the light-harvesting apparatus of purple bacteria Proc Natl Acad Sci USA 95 11 1998 5935 5941 (Pubitemid 28248942)
2. A. Loudet, and K. Burgess BODIPY dyes and their derivatives: syntheses and spectroscopic properties Chem Rev 107 11 2007 4891 4932 (Pubitemid 350225866)
3. G. Ulrich, R. Ziessel, and A. Harriman The chemistry of fluorescent bodipy dyes: versatility unsurpassed Angew Chem Int Ed 47 7 2008 1184 1201
4. R. Ziessel, G. Ulrich, and A. Harriman The chemistry of Bodipy: a new El Dorado for fluorescence tools New J Chem 31 4 2007 496 501 (Pubitemid 46558017)
5. R.W. Wagner, and J.S. Lindsey A molecular photonic wire J Am Chem Soc 116 21 1994 9759 9760 (Pubitemid 24981753)
6. F. Li, S.I. Yang, Y. Ciringh, J. Seth, C.H. Martin Iii, and D.L. Singh Design, synthesis, and photodynamics of light-harvesting arrays comprised of a porphyrin and one, two, or eight boron-dipyrrin accessory pigments J Am Chem Soc 120 39 1998 10001 10017 (Pubitemid 28473576)
7. M. Ravikanth, N. Agarwal, and D. Kumaresan Synthesis of energy donors appended dithiaporphyrin systems Chem Lett 29 7 2000 836 837
8. D. Kumaresan, I. Gupta, and M. Ravikanth Synthesis of 21-oxoporphyrin building blocks and energy donor appended systems Tetrahedron Lett. 42 48 2001 8547 8550 (Pubitemid 33043944)
9. R. Ziessel, C. Goze, and G. Ulrich Design and synthesis of alkyne-substituted boron in dipyrromethene frameworks Synthesis 6 2007 936 949
10. S. Goeb, and R. Ziessel Synthesis of novel tetrachromophoric cascade-type Bodipy dyes Tetrahedron Lett. 49 16 2008 2569 2574
11. C.W. Wan, A. Burghart, J. Chen, F. Bergström, LB Johansson, and M.F. Wolford Anthracene-BODIPY cassettes: syntheses and energy transfer Chem Eur J 9 18 2003 4430 4441
12. M. Bröring, R. Krüger, S. Link, C. Kleeberg, S. Kohler, and X. Xie Bis(BF2)-2,2′-bidipyrrins (BisBODIPYs): highly fluorescent BODIPY dimers with large stokes shifts Chem Eur J 14 10 2008 2976 2983
13. C. Goze, G. Ulrich, L. Charbonnire, M. Cesario, T. Prange, and R. Ziessel Cation sensors based on terpyridine functionalized boradiazaindacene Chem Eur J 9 16 2003 3748 3755
14. M. Galletta, S. Campagna, M. Quesada, G. Ulrich, and R. Ziessel The elusive phosphorescence of pyrromethene-BF2 dyes revealed in new multicomponent species containing Ru (ii)-terpyridine subunits Chem Commun 33 2005 4222 4224 (Pubitemid 41337188)
15. A. Harriman, G. Izzet, and R. Ziessel Rapid energy transfer in cascade-type Bodipy dyes J Am Chem Soc 128 33 2006 10868 10875 (Pubitemid 44277775)
16. G. Barin, M.D. Yilmaz, and E.U. Akkaya Boradiazaindacene (Bodipy)-based building blocks for the construction of energy transfer cassettes Tetrahedron Lett 50 15 2009 1738 1740
17. X. Zhang, Y. Xiao, and X. Qian Highly efficient energy transfer in the light harvesting system composed of three kinds of boronâ dipyrromethene derivatives Org Lett 10 1 2008 29 32
18. T. Bura, P. Retailleau, and R. Ziessel Efficient Synthesis of panchromatic dyes for energy concentration Angew Chem Int Ed. 49 37 2010 6659 6663
19. S. Diring, F. Puntoriero, F. Nastasi, S. Campagna, and R. Ziessel Star-shaped multichromophoric arrays from BODIPY dyes grafted on truxene core J Am Chem Soc 131 17 2009 6108 6110
20. K. Kim, C. Jo, S. Easwaramoorthi, J. Sung, D.H. Kim, and D.G. Churchill Crystallographic, photophysical, NMR spectroscopic and reactivity manifestations of the "8-heteroaryl effect" in 4,4-difluoro-8-(C(4)H(3)X)-4-bora-3a, 4a-diaza-s-indacene (X = O, S, Se) (BODIPY) systems Inorg Chem 49 11 2010 4881 4894
21. S. Kim, T.Y. Ohulchanskyy, A. Baev, and P.N. Prasad Synthesis and nanoparticle encapsulation of 3, 5-difuranylvinyl-boradiaza-s-indacenes for near-infrared fluorescence imaging J Mater Chem 19 20 2009 3181 3188
22. T.K. Khan, R.R.S. Pissurlenkar, M.S. Shaikh, and M. Ravikanth Synthesis and studies of covalently linked meso-furyl boron-dipyrromethene-ferrocene conjugates J Organomet Chem 697 2012 65 73
23. P. Hohenberg, and W. Kohn Inhomogeneous electron gas Phys Rev 136 3B 1964 B864 B871
24. X.H. Peng, A. Alizadeh, N. Bhate, K.K. Varanasi, S.K. Kumar, and S.K. Nayak First-principles investigation of strain effects on the energy gaps in silicon nanoclusters J Phys Condens Matter 19 2007 266212
25. X.H. Peng, S. Ganti, A. Alizadeh, P. Sharma, S.K. Kumar, and S.K. Nayak Strain-engineered photoluminescence of silicon nanoclusters Phys Rev B 74 3 2006 035339
26. E. Runge, and E.K.U. Gross Density-functional theory for time-dependent systems Phys Rev Lett. 52 12 1984 997 1000
27. T. Förster Transfer mechanisms of electronic excitation energy Radiat Res Suppl 1960 326 339
28. A.D. McNaught, and A. Wilkinson Compendium of chemical terminology: the gold book Second ed 1997 Blackwell Science
29. W. Qin, V. Leen, T. Rohand, W. Dehaen, P. Dedecker, and M. Van der Auweraer Synthesis, spectroscopy, crystal structure, electrochemistry, and quantum chemical and molecular dynamics calculations of a 3-anilino difluoroboron dipyrromethene dye J Phys Chem A 113 2 2009 439 447
30. Jaguar, version 7.8 2011 Schrödinger, LLC New York, NY
31. Rocks cluster v5.4 (Maverick) 2010 Rocks Cluster Group, San Diego Supercomputer Center, University of California San Diego
32. R.W. Wagner, and J.S. Lindsey Boron-dipyrromethene dyes for incorporation in synthetic multi-pigment light-harvesting arrays Pure Appl Chem. 68 7 1996 1373 1380 (Pubitemid 126454204)
33. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields J Phys Chem 98 45 1994 11623 11627
34. P.C. Hariharan, and J.A. Pople Natural population analysis (NPA) Theor Chim Acta 28 1973 213 222