Synthesis, spectroscopy, crystal structure determination, and quantum chemical calculations of BODIPY dyes with increasing conformational restriction and concomitant red-shifted visible absorption and fluorescence spectra

Chemistry - An Asian Journal

Volumn 5, Issue 9, 2010, Pages 2016-2026

  Leen, Volker ^a   Qin, Wenwu ^b   Yang, Wensheng ^b   Cui, Jie ^b   Xu, Chan ^b   Tang, Xiaoliang ^b   Liu, Weisheng ^b   Robeyns, Koen ^a   Van Meervelt, Luc ^a   Beljonne, David ^c   Lazzaroni, Roberto ^c   Tonnelé, Claire ^c   Boens, Noël ^a   Dehaen, Wim ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b LANZHOU UNIVERSITY   (China)

^c UNIVERSITY OF MONS   (Belgium)

Author keywords

BODIPY; Conformational mobility; Crystal structure; Fluorescent dyes; Solvent effect

Indexed keywords

4-METHYLPHENYL; ABSORPTION AND EMISSION SPECTRA; ABSORPTION AND FLUORESCENCE SPECTRA; BENZOFURANS; BODIPY; BOND ROTATIONS; CHEMICAL STRUCTURE; CONFORMATIONAL FLEXIBILITY; CONFORMATIONAL MOBILITY; CRYSTAL STRUCTURE DETERMINATION; ELECTRONIC EXCITATION; FLUORESCENCE EMISSION; FLUORESCENCE QUANTUM YIELD; FLUORESCENT DYES; IN-LINE; PLANARITY; POLARIZABILITIES; PRIMARY FACTORS; QUANTUM CHEMICAL CALCULATIONS; RED SHIFT; RED-SHIFTED; SOLVENT EFFECT; SOLVENT EFFECTS; TOTAL YIELD;

ABSORPTION; ABSORPTION SPECTROSCOPY; CHROMOPHORES; CONFORMATIONS; EMISSION SPECTROSCOPY; FLUORESCENCE; PALLADIUM; QUANTUM CHEMISTRY; QUANTUM YIELD; SOLVENTS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

CRYSTAL STRUCTURE;

EID: 77956482245     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000248     Document Type: Article

References (48)

1. A. Treibs, F.-H. Kreuzer, Liebigs Ann. Chem. 1968, 718, 208-223.
2. A. Loudet, K. Burgess, Chem. Rev. 2007, 107, 4891-4932
3. G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. 2008, 120, 1202-1219;
4. Angew. Chem. Int. Ed. 2008, 47, 1184-2101.
5. R. P. Haugland, The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10th ed., Invitrogen, Eugene, OR, 2005.
6. B. Valeur, Molecular Fluorescence. Principles and Applications, Wiley-VCH, Weinheim, Germany, 2002.
7. L. H. Thoresen, H. Kim, M. B. Welch, A. Burghart, K. Burgess, Synlett 1998, 1276-1278
8. A. Burghart, H. Kim, M. B. Welch, L. H. Thoresen, J. Reibenspies, K. Burgess, F. Bergström, L. B.-Å. Johansson, J. Org. Chem. 1999, 64, 7813-7819.
9. T. Rohand, W. Qin, N. Boens, W. Dehaen, Eur. J. Org. Chem. 2006, 4658-4663.
10. R. Rurack, M. Kollmannsberger, J. Daub, New J. Chem. 2001, 25, 289-292.
11. Z. Dost, S. Atilgan, E. U. Akkaya, Tetrahedron 2006, 62, 8484-8488.
12. V. Leen, E. Braeken, K. Luckermans, C. Jackers, M. Van der Au-weraer, N. Boens and W. Dehaen, Chem. Commun. 2009, 4515-4517.
13. J. Chen, J. A. Burghart, A. Derecskei-Kovacs, K. Burgess, J. Org. Chem. 2000, 65, 2900-2906.
14. M. Wada, S. Ito, H. Uno, T. Murashima, N. Ono, T. Urano, Y. Urano, Tetrahedron Lett. 2001, 42, 6711-6713
15. Z. Shen, H. Röhr, K. Rurack, H. Uno, M. Spieles, B. Schulz, G. Reck, N. Ono, Chem. Eur. J. 2004, 10, 4853-4871.
16. S. Goeb, R. Ziessel, Org. Lett. 2007, 9, 737-740.
17. K. Umezawa, Y. Nakamura, H. Makino, D. Citterio, K. Suzuki, J. Am. Chem. Soc. 2008, 130, 1550-1551.
18. K. Umezawa, A. Matsui, Y. Nakamura, D. Citterio, K. Suzuki, Chem. Eur. J. 2009, 15, 1096-1106.
19. A. B. Descalzo, H.-J. Xu, Z.-L. Xue, K. Hoffmann, Z. Shen, M. G. Weller, X.-Z. You, K. Rurack, Org. Lett. 2008, 10, 1581-1584
20. Y.-W. Wang, A. B. Descalzo, Z. Shen, X.-Z. You, K. Rurack, Chem. Eur. J. 2010, 16, 2887-2903.
21. M. Baruah, W. Qin, N. Basarić, W. M. De Borggraeve, N. Boens, J. Org. Chem. 2005, 70, 4152-4157.
22. M. Baruah, W. Qin, R. A. L. Vallée, D. Beljonne, T. Rohand, W. Dehaen, N. Boens, Org. Lett. 2005, 7, 4377-4380.
23. T. Rohand, M. Baruah, W. Qin, N. Boens, W. Dehaen, Chem. Commun. 2006, 266-268.
24. T. Rohand, J. Lycoops, S. Smout, E. Braeken, M. Sliwa, M. Van der Auweraer, W. Dehaen, W. M. De Borggraeve, N. Boens, Photochem. Photobiol. Sci. 2007, 6, 1061-1066.
25. C. Thivierge, R. Bandichhor, K. Burgess, Org. Lett. 2007, 9, 2135-2138.
26. G. Zeni, R. Larock, Chem. Rev. 2006, 106, 4644-4680.
27. The Cambridge Structural Database: a quarter of a million crystal structures and rising. F. H. Allen, Acta Crystallogr. Sect. B 2002, 58, 380-388 doi 10.1107/S0108768102003890.
28. The following represents a non-exhaustive list of BODIPY papers with spectroscopic/photophysical data; a) E. Vos de Wael, J. A. Par-doen, J. A. van Koeveringe, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1977, 96, 306-309
29. b)T. López Arbeloa, F. López Arbeloa, I. López Arbeloa, I. García-Moreno, A. Costela, R. Sastre, F. Amat-Guerri, Chem. Phys. Lett. 1999, 299, 315-321
30. A. Costela, I. García-Moreno, C. Gomez, R. C. Sastre, F. Amat-Guerri, M. Liras, F. López Arbeloa, J. Banuelos Prieto, I. López Arbeloa, J. Phys. Chem. A 2002, 106, 7736-7742
31. F. López Arbeloa, J. Banuelos Prieto, V. Martínez Martínez, T. Arbeloa López, I. López Arbeloa, Chem Phys Chem 2004, 5, 1762-1771
32. J. Banuelos Prieto, F. López Arbeloa, V. Martínez Martínez, T. Arbeloa López, F. Amat-Guerri, M. Liras, I. López Arbeloa, Chem. Phys. Lett. 2004, 385, 29-35
33. W. Qin, M. Baruah, M. Van der Auweraer, F. C. De Schryver, N. Boens, J. Phys. Chem. A 2005, 109, 7371-7384
34. W. Qin, T. Rohand, M. Baruah, A. Stefan, M. Van der Auweraer, W. Dehaen, N. Boens, Chem. Phys. Lett. 2006, 420, 562-568
35. Z. Li, R. Bitt-man, J. Org. Chem. 2007, 72, 8376-8382
36. Z. Ekmekci, M. D. Yilmaz, E. U. Akkaya, Org. Lett. 2008, 10, 461-464
37. L. Li, J. Han, B. Nguyen, K. Burgess, J. Org. Chem. 2008, 73, 1963-1970
38. E. Fron, E. Coutino-Gonzalez, L. Pandey, M. Sliwa, M. Van der Au-weraer, F. De Schryver, J. Thomas, Z. Dong, V. Leen, M. Smet, W. Dehaen, T. Vosch, New J. Chem. 2009, 33, 1490-1496
39. S. E. Braslavsky, Pure Appl. Chem. 2007, 79, 293-465.
40. R. A. L. Vallée, M. Van der Auweraer, F. C. De Schryver, D. Bel-jonne, M. Orrit, Chem Phys Chem 2005, 6, 81-91.
41. M. J. Kamlet, R. W. Taft, J. Am. Chem. Soc. 1976, 98, 377-383;
42. M. J. Kamlet, J. L. M. Abboud, R. W. Taft, J. Am. Chem. Soc. 1977, 99, 6027-6038.
43. J. Catalán, J. Phys. Chem. B 2009, 113, 5951-5960.
44. J. Catalán, H. Hopf, Eur. J. Org. Chem. 2004, 4694-4702.
45. J. Catalán in Handbook of Solvents, (Ed.: G. Wypych), ChemTec Publishing, Toronto, 2001, pp. 583-616.
46. J. Catalán, C. Díaz, Liebigs Ann. 1997, 1941-1949.
47. J. Catalán, C. Díaz, V. López, P. Pérez, J. L. G. de Paz, J. G. Rodriguez, Liebigs Ann. 1996, 1785-1794.
48. Y. Marcus, Chem. Soc. Rev. 1993, 22, 409-416.