1,3-bicyclo[1.1.1]pentanediyl: The shortest rigid linear connector of phenylated photochromic units and a 1,5-dimethoxy-9,10-di(phenylethynyl) anthracene fluorophore

Chemistry - A European Journal

Volumn 13, Issue 9, 2007, Pages 2503-2516

  De Meijere, Armin ^a,b   Ligang, Zhao ^a   Belov, Vladimir N ^c   Bossi, Mariano ^c   Noltemeyer, Matthias ^a   Hell, Stefan W ^c  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b KAdemCustomChem GmbH   (Germany)

^c MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

Bicyclo 1.1.1 pentane; Fluorescence; Molecular switches; Photochromism; Thiophenes

Indexed keywords

DERIVATIVES; FLUORESCENCE; PHOTOCHROMISM; RESONANCE; SUBSTITUTION REACTIONS; THIOPHENE;

FLUOROPHORE; MOLECULAR SWITCHES; PHOTOCHROMIC UNITS;

AROMATIC HYDROCARBONS;

1,5 DIMETHOXY 9,10 DI(PHENYLETHYNYL)ANTHRACENE; 1,5-DIMETHOXY-9,10-DI(PHENYLETHYNYL)ANTHRACENE; ANTHRACENE DERIVATIVE; BICYCLO COMPOUND; FLUORESCENT DYE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET RADIATION;

ANTHRACENES; BICYCLO COMPOUNDS; FLUORESCENT DYES; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; ULTRAVIOLET RAYS;

EID: 34250748073     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601316     Document Type: Article

References (76)

1. For a review, see: M. D. Levin, P. Kaszynski, J. Michl, Chem. Rev. 2000, 100, 169-234.
2. for the recent report, see: C. Mazal, O. Škarka, J. Kaleta, J. Michl, Org. Lett. 2006, 8, 749-752.
3. M. Messner, S. I. Kiwhushkov, A. de Meijere, Eur. J. Org. Chem. 2000, 1137-1155.
4. J. D. Rehm, B. Ziemer, G. Szeimies, Eur. J. Org. Chem. 1999, 2079-2085.
5. a) S. W. Hell, Phys. Lett. A 2004, 326, 140-145;
6. h) V. Westphal, S. W. Hell. Phys. Rev. Lett. 2005, 94, 143903;
7. c) S. W. Hell, S. Jakobs, L. Kastrup, Appl. Phys. A 2003, 77, 859-860;
8. d) M. Bossi, J. Fölling, M. Dyba, V. Weslphal, S. Hell, unpublished results.
9. 0, formalism and applications of RET, see: B. Wieb Wan Der Meer, G. Gorker III, S.-Y. Simon Chen, Resonance Energy Transfer (Theory and Data), Wiley-VCH, Weinheim, 1991.
10. For a review, see: F. M. Raymo, M. Tomasulo, J. Phys. Chem. A 2005, 109, 7343-7352.
11. Photochromic properties of diarylethylenes (a) and fulgides (b) have been reviewed: a) M. Irie, Chem. Rev. 2000, 100, 1685-1716;
12. c) Y. Yokoyama, Chem. Rev. 2000, 100, 1717-1739:
13. for the latest reports on diarylethylenes, see: c) T. Yamaguchi, M. Irie, J. Org. Chem. 2005, 70, 10323-10328;
14. d) Y. Moriyama, K. Matsuda, N. Tanifuji, S. Irie, M. Irie, Org. Lett. 2005, 7, 3315-3318;
15. e) Y.-C. Jeong, S. I. Yang, E. Kim, K.-H. Ahn. Tetrahedron 2006, 62, 5855-5861.
16. In some cases it is difficult to identify the substructure of the fluorophore, which may be a part of the photochromic diarylethene: a) G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188-1191:
17. Angew. Chem. Int. Ed. Engl. 1995, 34, 1119-1122;
18. b) G. M. Tsivgoulis, J.-M. Lehn, Chem. Eur. J. 1996, 2, 1399-1406;
19. c) M. Takeshita, M. Irie, Chem. Lett. 1998, 1123-1124;
20. d) A. Osuka, D. Fujikane, H. Shinmori, S. Kobatake, M. Irie, J. Org. Chem. 2001, 66, 3913-3923;
21. e) J. Ern, A. T. Bens, H.-D. Martin, S. Mukamel, S. Tretiak, K. Tsyganenko, K. Kuldova, H. P. Trommsdorf, C. Kryshi. J, Phys. Chem. A 2001, 105, 1741-1749;
22. f) K. Yagi, C. F. Song, M. Irie, J. Org. Chem. 2001, 66, 5419-5423;
23. g) T. Kawai, T. Sasaki, M. Irie, Chem. Commun. 2001, 711-712;
24. h) H. Cho, E. Kim, Macromolecules 2002, 35, 8684-8687;
25. i) T. A. Golovkova, D. V. Kozlov, D. C. Neekers, J. Org. Chem. 2005, 70, 5545-5549;
26. j) A. FernándezAcebes, J.-M. Lehn, Chem. Eur. J. 1999, 5, 3285-3292;
27. k) T. B. Norsten, M. R. Branda, Adv. Mater. 2001, 13, 347-349;
28. l) A. L. Myles, M. R. Branda, Adv. Funct. Mater. 2002, 12, 167-173;
29. m) M.-S. Kim, T. Kawai, M. Irie, Chem. Lett. 2001, 702-703;
30. n) R. T. F. Jukes, V. Adamo, F. Hartl, P. Besler, L. De Cola, Inorg. Chem. 2004, 43, 2779-2792.
31. a) J. M. Endtner, F. Effenberger, A. Hartschuh, H. Port. J. Am. Chem. Soc. 2000, 122, 3037-3046;
32. b) L. Giordano, T. M. Jovin, M. Irie, E. A. Jares-Erijman, J. Am. Chem. Soc. 2002, 124, 7481-7489;
33. c) M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759-760;
34. T. Fukaminato, T. Sasaki, T. Kawai, N. Tamai, M. Irie, J. Am. Chem. Soc. 2004, 126, 14843-14849;
35. d) M. Frigoli, G. H. Mehl, Chem. Eur. J. 2004, 10, 5243-5250.
36. a) M. Irie, K. Sakemura, M. Okinaka, K. Uchida. J. Org. Chem. 1995, 60, 8305-8309;
37. b) the analogue of the compound 1 without methyl groups at the positions 4 and 4′ has also been described: M. Irie, T. Lifka, S. Kohatake, N. Kato, J. Am. Chem. Soc. 2000, 122, 4871-4876.
38. a) S. Kobatake, Y. Matsumoto, M. Irie, Angew. Chem. 2005, 117, 2186-2189:
39. Angew. Chem. Int. Ed. 2005, 44, 2148-2151;
40. b) prototypes of the photochromic units 1-3 without methyl groups at the positions 4 and 4′ have also been described: K. Shibata, S. Kobatake, M. Irie, Chem. Lett. 2001, 618-619.
41. a) P. J. Hanhela, D. B. Paul, Aust. J. Chem. 1981, 34, 1701-1717;
42. FI = 1 (see ref. [9c]).
43. 4 in THF to pure 2,4-dibromo-3,5-dimethylthiophene.
44. 2 (M. Janda, J. Šrogl, I. Stibor, M. Nimec, P. Vapatrna, Synthesis 1972, 545-547) is very difficult to control, and this protocol also does not afford a reasonably pure product.
45. A procedure similar to a previously reported method was used; see: J. Froehlich, C. Hameter, W. Kalt, Monatsh, Chem. 1996, 127, 325-330.
46. a) M. Kumada. K. Tamao, K. Sumitani. Org. Synth. 1978, 58, 127-133;
47. b) M. Takeshita, M. Tashiro, J. Org. Chem. 1991, 56, 2837-2845.
48. G. Consiglio, D. Spinelli, S. Gronowitz, A.-B. Hoernfeldt, B. Maltesson, R. Noto, Chem. Soc. Perkin 2 1982, 625-630.
49. M. A. Keegstra, T. H. A. Peters, L. Brandsma, Tetrahedron 1992, 48, 3633-3652. An alternative preparation of 14 is much more difficult and gave worse results. Thus. 2,4-dibromothiophene in the presence of CuBr (20 mol%) reacted with MeONa in MeOH to give predominantly 4-bromo-2-methoxythiophene, which could be isolated in 41 % yield by a difficult Chromatographic separation from the regioisomer and the unreacted starting material. Kumada coupling of 4-bromo-2-methoxythiophene with MeMgCl then afforded the required compound 14.
50. A. Hallberg, S. Gronowitz, Chem. Scr. 1980, 16, 38-41.
51. S. Kobatake, M. Irie, Tetrahedron 2003, 59, 8359-8364.
52. 2 with iodine for the iodination of aromatics, see: Q. Li, A. V. Rukavishnikov, P. A. Petukhov, T. O. Zaikova, J. F. W. Keana, Org. Lett. 2002, 4, 3631-3634. In our hands other oxidizing agents gave poorer results.
53. K. M. Lynch, W. P. Dailey, Org. Synth. 1997, 75, 98-105.
54. These reagents were used for the monomethylation of 1-hydroxy-5-methoxy- 9,10-anthraquinone; a) S. Laugraud, A. Guingant, C. Chassagnard, J. d'Angelo, J. Org. Chem. 1988, 53, 1557-1561);
55. 2 in DMF with NaH at 80°C for 24 h gave the desired product in 75% yield after column chromatography (cf.: b) H. Quast, H.-L. Fuchbauer, Chem. Ber. 1986, 119, 1016-1038);
56. c) P. N. Preston, J. Chem. Soc. Perkin Trans. 1 1983, 1439-1441.
57. See: W. Ried, W. Donner, W. Schlegelmilch, Chem. Ber. 1961, 94, 1051-1058.
58. W. Chodkiewicz, P. Cadiot, C. K. Chim. 1958, 247, 2383-2385.
59. It may not only arise by an oxidative coupling of 26, but also from the corresponding tin acetylide, which may be present as an impurity in the crude starting material 26.
60. a) J. Sice, J. Org. Chem. 1954, 19, 70-73;
61. b) S. Gronowitz, K. Lawitz, Chem. Scr. 1983, 22, 265-266;
62. c) H.-J. Bertram, M. Guentert, R. Hopp, H. Sommer, P. Werkhoff, New J. Phys. 2006, 8, 275-284.
63. max ≈ 600 nm, and its solutions turned blue (cf.: K. Yagi, C. F. Soong, M. Irie, J. Org. Chem. 2001, 66, 5419-5423).
64. CCDC-290971 and -290972 contain the supplementary crystallogniphic 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.
65. M. Morimoto, M. Irie, Chem. Commun. 2005, 3895-3905 and references therein.
66. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry. VCH, Weinheim, 1970.
67. This prerequisite is not sufficient: M. Irie et al. reported that if the distance between the reactive carbon atoms in the antiparallel orientation exceeds 4.2 Å, the photocyclization does not occur. If this distance is shorter than 4.0 Å, the ring-closing reaction may be efficient: a) S. Kobatake, K. Uchida, E. Tsuchida, M. Irie, Chem. Commun. 2002, 2804-2805;
68. b) K. Shibata, K. Muto, S. Kobatake, M. Irie, J. Phys. Chem. A 2002, 106, 209-214.
69. 2 which were obtained from the bromides 42-Br/43-Br and further treated (without isolation) with an excess of 1,3-bis-(4-iodophenyl) adamantane, were reported to give the corresponding mono-coupling products in 28 and 18% yield, respectively (ref. [9c]).
70. M. H. Deniel, D. Lavabre, J. C. Mieheau, in Organic Photochromic and Thermochromic Compounds, Vol 2: Physicochemical Studies, Biologial Applications, and Thermochromium (Eds.: J. C. Crano, R. J. Guglielmetti), Kluwer Academic, Plenum Publishers, New York, 1999, pp. 167-209.
71. a) Y. Goldberg, H. Alper, J. Org. Chem. 1993, 58, 3072-3075;
72. b) M. J. Marsella, G. Piao, F. S. Tham, Synthesis 2002, 1133-1135.
73. This procedure is similar to the method previously reported, see: J. Froehlich, C. Hameter, W. Kalt, Monatsh. Chem. 1996, 127, 325-330.
74. S. Kobatake, M. Irie, Tetrahedron 2003, 59, 8359-8364.
75. Signals of the fluorinated carbon atoms were not registered, due to low intensity.
76. This compound had previously been prepared by M. Irie et al. and used for further reactions without characterization (see Supporting Information of ref. [9c]).