Trimeric cyclic assemblies of calix[4]arene-tethered bismerocyanines

Angewandte Chemie - International Edition

Volumn 48, Issue 33, 2009, Pages 6165-6168

  Lohr, Andreas ^a   Uemura, Shinohu ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Calixarenes; Dipolar aggregation; Dyes pigments; Macrocycles; Self assembly

Indexed keywords

BINDING MOTIF; CALIX[4]ARENES; CALIXARENES; DIPOLAR AGGREGATION; DYES/PIGMENTS; MACROCYCLES; MEROCYANINE DYE;

CHROMOPHORES; MATHEMATICAL MODELS; SELF ASSEMBLY;

PHENOLS;

EID: 70349900575     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200902299     Document Type: Article

References (66)

1. a) J.-M. Lehn, Supramolecular Chemistry, VCH Weinheim, 1995;
2. b) Comprehensive Supramolecular Chemistry (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle, J.-M. Lehn), Pergamon, Oxford, 1996.
3. For general reviews on hydrogen-bonded and metallosupramo-lecular cyclic structures, see: a) M. Fujita, Chem. Soc. Rev. 1998, 27, 417-425;
4. b) P. J. Stang, B. Olenyuk, Acc. Chem. Res. 1997, 30, 502-518;
5. c) B. J. Holliday, C. A. Mirkin. Angew. Chem. 2001, 113, 2076-2097;
6. Angew. Chem. Int. Ed. 2001, 40, 2022-2043;
7. d) L. J. Prins, D. N. Reinhoudt, P. Timmerman, Angew. Chem. 2001, 113, 2446-2492;
8. Angew. Chem. Int. Ed. 2001, 40, 2382-2426;
9. e) F. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556-1578;
10. Angew. Chem. Int. Ed. 2002, 41, 1488-1508;
11. f) M. Schmittel, V. Kalsani, Top. Curr. Chem. 2005, 245, 1-53.
12. For general reviews on cyclic dye arrays, see: a) Y. Nakamura, N. Aratani, A. Osuka, Chem. Soc. Rev. 2007, 36, 831-845;
13. b) A. Satake, Y. Kobuke, Tetrahedron 2005, 61, 13-41;
14. c) C.-C. You, R. Dobrawa, C. R. Saha-Möller, F. Würthner, Top. Curr. Chem. 2005, 258, 39-82.
15. For example of noncovalent cyclic porphyrin arrays, see: a) S. Anderson, H. L. Anderson, A. Bashall, M. McPartlin, J. K. M. Sanders, Angew. Chem. 1995, 107, 1196-1200;
16. Angew. Chem. Int. Ed. Engl. 1995, 34, 1096-1099;
17. b) S. Knapp, J. Vasudevan, T. J. Emge, B. H. Arison, J. A. Potenza, H. J. Schugar, Angew. Chem. 1998, 110, 2537-2540;
18. Angew. Chem. Int. Ed. 1998, 37, 2368-2370;
19. c) H. A. M. Biemans, A. E. Rowan, A. Verhoeven, P. Vanoppen, L. Latterini, J. Foekerna, A. P. H. J. Schenning, E. W. Meijer, F. C. de Schryver, R. J. M. Nolte, J. Am. Chem. Soc. 1998, 120, 11054-11060;
20. d) J. Li, A. Ambroise, S. I. Yang, J. R. Diers, J. Seth, C. R. Wack, D. F. Bocian, D. Holten, J. S. Lindsey, J. Am. Chem. Soc. 1999, 121, 8927-8940;
21. e) O. Mongin, N. Hoyler, A. Gossauer, Eur. J. Org. Chem. 2000, 1193-1197;
22. f) R. A. Haycock, C. A. Hunter, D. A. James, U. Michelsen, L. R. Sutton, Org. Lett. 2000, 2, 2435-2438;
23. g) C. Ikeda, N. Nagahara, N. Yoshioka, H. Inoue, New J. Chem. 2000, 24, 897-902;
24. h) X. Shi, K. M. Barkigia, J. Fajer, C. M. Drain, J. Org. Chem. 2001, 66, 6513-6522;
25. i) F. Hajjaj, Z. S. Yoon, M.-C. Yoon, J. Park, A. Satake, D. Kim, Y. Kobuke, J. Am. Chem. Soc. 2006, 128, 4612-4623.
26. a) F. Würthner, S. Yao, Angew. Chem. 2000, 112, 2054-2057;
27. Angew. Chem. Int. Ed. 2000, 39, 1978-1981;
28. b) F. Würthner, S. Yao, T. Debaerdemaker, R. Wortmann, J. Am. Chem. Soc. 2002, 124, 9431-9447.
29. a) S. Yao, U. Beginn, T. Gress, M. Lysetska, F. Würthner, J. Am. Chem. Soc. 2004, 126, 8336-8348;
30. b) A. Lohr, T. Gress, M. Deppisch, M. Knoll, F. Würthner, Synthesis 2007, 3073-3082.
31. A. Lohr, M. Grüme, F. Würthner, Chem. Eur. J. 2009, 15, 3691-3705.
32. For the optical properties and formation of intramolecular aggregates of tethered merocyanine or squaraine dyes, see: a) T. Katoh, Y. Inagaki, R. Okazaki, J. Am. Chem. Soc. 1998, 120, 3623-3628;
33. b) L. Lu, R. J. Lachicotte, T. L. Penner, J. Perlstein, D. G. Whitten, J. Am. Chem. Soc. 1999, 121, 8146-8156;
34. c) E. N. Ushakov, S. P. Gromov, O. A. Fedorova, Y. V. Pershina, M. V. Alfimov, F. Barigelletti, L. Flamigni, V. Balzani, J. Phys. Chem. A 1999, 103, 11188-11193;
35. d) S. Zeena, G. K. Thomas, J. Am. Chem. Soc. 2000, 123, 7859-7865;
36. e) E. Arunkumar, P. Chithra, A. Ajayaghosh, J. Am. Chem. Soc. 2004, 126, 6590-6598.
37. For general reviews on calixarenes, see: a) Calixarenes 2001 (Eds.; Z. Asfari, V. Bohmer, J. Harrowfield), Kluwer Academic Publishers, Dordrecht, 2001;
38. b) C. D. Gutsche, Calixarenes Revisited, The Royal Society of Chemistry, Letchworth, 1998;
39. c) V. Böhmer, Angew. Chem. 1995, 107, 785-818;
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745;
41. d) Calixarenes in Action (Eds.: L. Mandolini, R. Ungaro), Imperial College Press, London, 2000.
42. For dye-functionalized calixarenes, see for example: a) P. J. A. Kenis, E. G. Kerver, B. H. M. Snellink-Ruël, G. J. van Hummel, S. Harkema, M. C. Flipse, R. H. Woudenberg, J. F. J. Engbersen, D. N. Reinhoudt, Eur. J. Org. Chem. 1998, 1089-1098;
43. b) E. J. Kim, J.-I. Choe, S.-K. Chang, Tetrahedron Lett. 2003, 44, 5299-5302;
44. c) H.-h. Yu, B. Xu, T. M. Swager, J. Am. Chem. Soc. 2003, 725, 1142-1143;
45. d) C. Hippius, F. Schlosser, M. O. Vysotsky, V. Böhmer, F. Würthner, J. Am. Chem. Soc. 2006, 128, 3870-3871.
46. a) J. Rebek, Jr., B. Askew, M. Killoran, D. Nemeth, F.-T Lin, J. Am. Chem. Soc. 1987, 109, 2426-2431;
47. b) S. C. Zimmerman, M. Mrksich, M. Baloga, J. Am. Chem. Soc. 1989, 111, 8528-8530.
48. a) M. Kasha, H. R. Rawls, M. Ashraf El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392;
49. b) A. S. Davydov, Theory of Molecular Excitons, Plenum Press, New York, 1971;
50. c) H. Fidder, J. Knoester, D. A. Wiersma, J. Chem. Phys. 1991, 95, 7880-7890.
51. The transition dipole moment of the merocyanine chromophore is oriented along the long molecular axis.
52. a) K. A. Connors, Binding Constants, Wiley, New York, 1987;
53. b) R. B. Martin, Chem. Rev. 1996, 96, 3043-3064;
54. c) Z. Chen, A. Lohr, C. R. Saha-Möller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564-584.
55. a) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2563-2565;
56. b) G. Ercolani, J. Phys. Chem. B 1998, 102, 5699-5703;
57. c) G. Ercolani, Chem. Commun. 2001, 1416-1417;
58. d) G. Ercolani, J. Am. Chem. Soc. 2003, 125, 16097-16103.
59. For a review on mass spectroscopy in supramolecular chemistry, see: B. Baytekin, H. T. Baytekin, C. A. Schalley, Org. Biomol. Chem. 2006, 4, 2825-2841.
60. The given m/z values corresponds to the average isotopic mass because the isotopic pattern of the singly charged trimeric complex of 2 could not be resolved in the MALDI-TOF measurements (see the Supporting Information, Figure S2).
61. r = 4.81), we expect a higher aggregation constant in the former solvent.
62. a) S. De Feyter, F. C. De Schryver, Chem. Soc. Rev. 2003, 32, 139-150;
63. b) S. De Feyter, F. C. De Schryver, J. Phys. Chem. B 2005, 109, 4290-4302.
64. Hyperchem; Hypercube Inc.: 1115 NW 4th Street, Gainesville, FL 32601, USA.
65. a) P. Timmerman, R. H. Vreekamp, R. Hulst, W. Verboom, D. N. Reinhoudt, K. Rissanen, K. A. Udachin, J. Ripmeester, Chem. Eur. J. 1997, 3, 1823-1832;
66. b) L. J. Prins, C. Thalacker, F. Würthner, P. Timmerman, D. N. Reinhoudt, Proc. Natl. Acad. Sci. USA 2001, 98, 10042-10045.