Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties

Tetrahedron

Volumn 65, Issue 50, 2009, Pages 10348-10354

  Skibiński, Maciej ^a   Gómez, Rafael ^b   Lork, Enno ^a   Azov, Vladimir A ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Cyclic voltammetry; Molecular recognition; Molecular tweezers; Tetrathiafulvalenes; X ray

Indexed keywords

TETRATHIAFULVALENE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 70350714953     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.052     Document Type: Article

References (78)

1. Wudl F., Wobschall D., and Hufnagel E.J. J. Am. Chem. Soc. 94 (1972) 670-672
2. Ferraris J., Cowan D.O., Walatka Jr. V., and Perlstein J.H. J. Am. Chem. Soc. 95 (1973) 948-949
3. Bendikov M., Wudl F., and Perepichka D.F. Chem. Rev. 104 (2004) 4891-4945
4. Bryce M.R. J. Mater. Chem. 10 (2000) 589-598
5. Nielsen M.B., Lomholt C., and Becher J. Chem. Soc. Rev. 29 (2000) 153-164
6. Krief A. Tetrahedron 42 (1986) 1209-1252
7. Segura J.L., and Martín N. Angew. Chem., Int. Ed. 40 (2001) 1372-1409
8. Fabre J.M. Chem. Rev. 104 (2004) 5133-5150
9. Gorgues A., Hudhomme P., and Sallé M. Chem. Rev. 104 (2004) 5151-5184
10. Canevet D., Sallé M., Zhang G., Zhang D., and Zhu D. Chem. Commun. (2009) 2245-2269
11. Gómez R., Segura J.L., and Martín N. Org. Lett. 2 (2000) 1585-1587
12. Gómez R., Segura J.L., and Martín N. J. Org. Chem. 65 (2000) 7566-7574
13. Zhou Y., Zhang D., Zhu L., Shuai Z., and Zhu D. J. Org. Chem. 71 (2006) 2123-2130
14. Delogu G., Fabbri D., Dettori M.A., Sallé M., Le Derf F., Blesa M.-J., and Allain M. J. Org. Chem. 71 (2006) 9096-9103
15. Devonport W., Bryce M.R., Marshallsay G.J., Moore A.J., and Goldenberg L.M. J. Mater. Chem. 8 (1998) 1361-1372
16. Bryce M.R., Devonport W., Goldberg L.M., and Wang C. Chem. Commun. (1998) 945-951
17. González A., Segura J.L., and Martín N. Tetrahedron Lett. 41 (2000) 3083-3086
18. Jeppesen J.O., Nielsen M.B., and Becher J. Chem. Rev. 104 (2004) 5115-5131
19. Pease A.R., Jeppesen J.O., Stoddart J.F., Luo Y., Collier C.P., and Heath J.R. Acc. Chem. Res. 34 (2001) 433-444
20. Becher J., Jeppesen J.O., and Nielsen K. Synth. Met. 133-134 (2003) 309-315
21. Moonen N.N.P., Flood A.H., Fernández J.M., and Stoddart J.F. Top. Curr. Chem. 262 (2005) 99-132
22. Chen C.-W., and Whitlock Jr. H.W. J. Am. Chem. Soc. 100 (1978) 4921-4922
23. Zimmerman S.C., and VanZyl C.M. J. Am. Chem. Soc. 109 (1987) 7894-7896
24. Rowan A.E., Elemans J.A.A.W., and Nolte R.J.M. Acc. Chem. Res. 32 (1999) 995-1006
25. Klärner F.-G., and Kahlert B. Acc. Chem. Res. 36 (2003) 919-932
26. Harmata M. Acc. Chem. Res. 37 (2004) 862-873
27. Petitjean A., Khoury R.G., Kyritsakas N., and Lehn J.-M. J. Am. Chem. Soc. 126 (2004) 6637-6647
28. Colquhoun H.M., and Zhu Z. Angew. Chem., Int. Ed. 43 (2004) 5040-5045
29. Pardo C., Sesmilo E., Gutiérrez-Puebla E., Monge A., Elguero J., and Fruchier A. J. Org. Chem. 66 (2001) 1607-1611
30. Kurebayashi H., Sakaguchi M., Okajima T., Haino T., Usui S., and Fukazawa Y. Tetrahedron Lett. 40 (1999) 5545-5548
31. Kurebayashi H., Haino T., and Fukazawa Y. Tetrahedron Lett. 41 (2000) 477-480
32. Kurebayashi H., Haino T., Usui S., and Fukazawa Y. Tetrahedron 57 (2001) 8667-8674
33. Iwamoto H., Takahashi N., Maeda T., Hidaka Y., and Fukazawa Y. Tetrahedron Lett. 46 (2005) 6839-6842
34. Iwamoto H., Hidaka Y., and Fukazawa Y. Tetrahedron Lett. 49 (2008) 277-280
35. Chiang P.-T., Cheng P.-N., Lin C.-F., Liu Y.-H., Lai C.-C., Peng S.-M., and Chiu S.-H. Chem.-Eur. J. 12 (2006) 865-876
36. Cheng K.-W., Lai C.-C., Chianga P.-T., and Chiu S.-H. Chem. Commun. (2006) 2854-2856
37. Chiang P.-T., Chen N.-C., Lai C.-C., and Chiu S.-H. Chem.-Eur. J. 14 (2008) 6546-6552
38. Tachikawa T., Izuoka A., and Sugawara T. J. Chem. Soc., Chem. Commun. (1993) 1227-1229
39. Tachikawa T., Izuoka A., and Sugawara T. Solid State Commun. 88 (1993) 207-209
40. Fujiwara H., Arai E., and Kobayashi H. J. Mater. Chem. 8 (1998) 829-831
41. Poulsen T., Nielsen K.A., Bond A.D., and Jeppesen J.O. Org. Lett. 9 (2007) 5485-5488
42. Nielsen K.A., Sarova G.H., Martín-Gomis L., Fernández-Lázaro F., Stein P.C., Sanguinet L., Levillain E., Sessler J.L., Guldi D.M., Sastre-Santos A., and Jeppesen J.O. J. Am. Chem. Soc. 130 (2008) 460-462
43. Nielsen K.A., Martín-Gomis L., Sarova G.H., Sanguinet L., Gross D.E., Fernández-Lázaro F., Stein P.C., Levillain E., Sessler J.L., Guldi D.M., Sastre-Santos A., and Jeppesen J.O. Tetrahedron 64 (2008) 8449-8463
44. Azov V.A., Gómez R., and Stelten J. Tetrahedron 64 (2008) 1909-1917
45. Plater M.J., Aiken S., and Bourhill G. Tetrahedron 58 (2002) 2405-2413
46. Cho H.S., Jeong D.H., Cho S., Kim D., Matsuzaki Y., Tanaka K., Tsuda A., and Osuka A. J. Am. Chem. Soc. 124 (2002) 14642-14654
47. Bonifazi D., Accorsi G., Armaroli N., Song F.Y., Palkar A., Echegoyen L., Scholl M., Seiler P., Jaun B., and Diederich F. Helv. Chim. Acta 88 (2005) 1839-1884
48. Wang C., Batsanov A.S., Bryce M.R., and Howard J.A.K. Synthesis (1998) 1615-1618
49. Simonsen K.B., Svenstrup N., Lau J., Simonsen O., Mørk P., Kristensen G.J., and Becher J. Synthesis (1996) 407-418
50. Svenstrup N., Rasmussen K.M., Hansen T.K., and Becher J. Synthesis (1994) 809-812
51. Röhrich J., and Müllen K. J. Org. Chem. 57 (1992) 2374-2379
52. Ried W., and Bodem H. Chem. Ber. 89 (1956) 2328-2331
53. Rivera J.M., Martin T., and Rebek Jr. J. J. Am. Chem. Soc. 123 (2001) 5213-5220
54. González M., Illescas B., Martín N., Segura J.L., Seoane C., and Hanack M. Tetrahedron 54 (1998) 2853-2866
55. Moses P.R., and Chambers J.Q. J. Am. Chem. Soc. 96 (1974) 945-946
56. Röhrich J., Wolf P., Enkelmann V., and Müllen K. Angew. Chem., Int. Ed. Engl. 27 (1988) 1377-1379
57. Simonsen K.B., Thorup N., and Becher J. Synthesis (1997) 1399-1404
58. Nielsen M.B., Thorup N., and Becher J. J. Chem. Soc., Perkin Trans. 1 (1998) 1305-1308
59. Jørgensen M., Lerstrup K.A., and Bechgaard K. J. Org. Chem. 56 (1991) 5684-5688
60. Blanchard P., Svenstrup N., and Becher J. Chem. Commun. (1996) 615-616
61. Spanggaard H., Prehn J., Nielsen M.B., Levillain E., Allain M., and Becher J. J. Am. Chem. Soc. 122 (2000) 9486-9494
62. Le Derf F., Levillain E., Trippé G., Gorgues A., Sallé M., Sebastian R.-M., Caminade A.-M., and Majoral J.-P. Angew. Chem., Int. Ed. 40 (2001) 224-227
63. Bouguessa S., Hervé K., Golhen S., Ouahab L., and Fabre J.-M. New J. Chem. 27 (2003) 560-564
64. Lyskawa J., Sallé M., Balandier J.-Y., Le Derf F., Levillain E., Allain M., Viel P., and Palacin S. Chem. Commun. (2006) 2233-2235
65. Frei M., Diederich F., Tremont R., Rodríguez T., and Echegoyen L. Helv. Chim. Acta 89 (2006) 2040-2057
66. The splitting of the second oxidation wave has been also observed for TTF-containing cyclophanes only when the TTF moieties were forced to stay in close proximity to each other:
67. Takimiya K., Imamura K., Shibata Y., Aso Y., Ogura F., and Otsubo T. J. Org. Chem. 62 (1997) 5567-5574
68. See Ref. 25c.
69. For examples of TCNQ and TNF complexes with TTFs in solid state, see:
70. Moore A.J., Bryce M.R., Batsanov A.S., Heaton J.N., Lehmann C.W., Howard J.A.K., Robertson N., Underhill A.E., and Perepichka I.F. J. Mater. Chem. 8 (1998) 1541-1550
71. Batsanov A.S., Bryce M.R., Chesney A., Howard J.A.K., John D.E., Moore A.J., Wood C.L., Gershtenman H., Becker J.Y., Khodorkovsky V.Y., Ellern A., Bernstein J., Perepichka I.F., Rotello V., Gray M., and Cuello A.O. J. Mater. Chem. 11 (2001) 2181-2191
72. See Supplemetary data for details of the binding studies.
73. Saito G., and Ferraris J.P. Bull. Chem. Soc. Jpn. 53 (1980) 2141-2145
74. Jeppesen J.O., Takimiya K., Jensen F., Brimert T., Nielsen K., Thorup N., and Becher J. J. Org. Chem. 65 (2000) 5794-5805
75. Jeppesen J.O., and Becher J. Eur. J. Org. Chem. (2003) 3245-3266
76. Nielsen M.B., Jeppesen J.O., Lau J., Lomholt C., Damgaard D., Jacobsen J.P., Becher J., and Stoddart J.F. J. Org. Chem. 66 (2001) 3559-3563
77. Sheldrick G.M. SHELXS97: Program for Crystal Structure Solution (1997), University of Göttingen, Göttingen, Germany
78. Sheldrick G.M. SHELXL97: Program for Crystal Structure Refinement (1997), University of Göttingen, Göttingen, Germany