Self-assembly of supramolecular oligo-phenylene-ethynylene wires consisting of double Hamilton receptor modified OPE rods and a tetraphenylporphyrin cyanurate

Tetrahedron

Volumn 64, Issue 50, 2008, Pages 11480-11489

  Wessendorf, Florian ^a   Hirsch, Andreas ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Hamilton receptor; Hydrogen bonding; Oligo phenylene ethynylene; Porphyrins; Self assembly

Indexed keywords

CYANURIC ACID; PHENAZONE; TETRAPHENYLPORPHYRIN DERIVATIVE;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; FLUORESCENCE SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 55049107536     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.054     Document Type: Article

References (61)

1. Detert H., Schollmeyer D., and Sugiono E. Eur. J. Org. Chem. (2001) 2927-2938
2. Weder C., and Wrighton M.S. Macromolecules 29 (1996) 5157-5165
3. Burroughes J.H., Bradley D.D.C., Brown A.R., Marks R.N., Mackay K., Friend R.H., Burns P.L., and Holmes A.B. Nature 347 (1990) 539-541
4. Ohmori Y., Uchida M., Muro K., and Katsumi Y. Jpn. J. Appl. Phys. 30 (1991) 1938-1940
5. Berggren M., Inganas O., Gustafsson G., Rasmusson J., Andersson M.R., Hjertberg T., and Wennerström O. Nature 372 (1994) 444-446
6. Rajca A., Rajca S., Pink M., and Miyasaka M. Synlett (2007) 1799-1822
7. Murphy A.R., and Fréchet J.M.J. Chem. Rev. 107 (2007) 1066-1096
8. Ajayaghosh A., and Praveen V.K. Acc. Chem. Res. 40 (2007) 644-656
9. Tomović Z., van Dongen J., George S.J., Xu H., Pisula W., Leclere W., Smulders M.M.J., de Feyter S., Meijer E.W., and Schenning A.H.P.J. J. Am. Chem. Soc. 129 (2007) 16190-16196
10. Watson M.D., Fechtenkötter A., and Müllen K. Chem. Rev. 101 (2001) 1267-1300
11. Grimsdale A.C., and Müllen K. Angew. Chem., Int. Ed. 44 (2005) 5592-5629
12. Schenning A.P.H.J., and Meijer E.W. Chem. Commun. (2005) 3245-3258
13. Hoeben F.J.M., Jonkheijm P., Meijer E.W., and Schenning A.P.H.J. Chem. Rev. 105 (2005) 1491-1546
14. Wu J., Pisula W., and Müllen K. Chem. Rev. 107 (2007) 718-747
15. Yamamoto Y., Fukushima T., Suna Y., Ishii N., Saeki A., Seki S., Tagawa S., Taniguchi M., Kawai T., and Aida T. Science 314 (2006) 1761-1764
16. Yamamoto Y., Fukushima T., Jin W., Kosaka A., Hara T., Nakamura T., Saeki A., Seki S., Tagawa S., and Aida T. Adv. Mater. 18 (2006) 1297-1300
17. Xiao S., Tang J., Beetz T., Guo X., Tremblay N., Siegrist T., Zhu Y., Steigerwald M., and Nuckolls C. J. Am. Chem. Soc. 128 (2006) 10700-10701
18. Shklyarevskiy I.O., Jonkheijm P., Stutzmann N., Wasserberg D., Wondergem H.J., Christianen P.C.M., Schenning A.P.H.J., de Leeuw D.M., Tomović Z., Wu J., Müllen K., and Maan J.C. J. Am. Chem. Soc. 127 (2005) 16233-16237
19. Jonkheijm P., Stutzmann N., Chen Z., de Leeuw D.M., Meijer E.W., Schenning A.P.H.J., and Würthner F. J. Am. Chem. Soc. 128 (2006) 9535-9540
20. Secker D., and Weber H. Phys. Status Solidi B 244 (2007) 4176-4180
21. Lörtscher E., Weber H., and Riel H. Phys. Rev. Lett. 98 (2007) 176807
22. Ochs R., Secker D., Elbing M., Mayor M., and Weber H. Faraday Discuss. 131 (2006) 281-289
23. Elbing M., Ochs R., Koentopp M., Fischer M., von Hänisch C., Weigend F., Evers F., Weber H., and Mayor M. Proc. Natl. Acad. Sci. U.S.A. 102 (2005) 8815-8820
24. van Ruitenbeek J., Scheer E., and Weber H. Contacting Individual Molecules Using Mechanically Controllable Break Junctions. In: Cuniberti G., Fagas G., and Richter K. (Eds). Introducing Molecular Electronics (2005), Springer, Berlin, Heidelberg 253-274
25. Mas-Torrent M., den Boer D., Durkut M., Hadley P., and Schenning A.P.H.J. Nanotechnology 15 (2004) 265-269
26. Akagi K., Piao G., Kaneko S., Sakamaki K., Sirakawa H., and Kyotani M. Science 282 (1998) 1683-1686
27. Xia Y., Yang P., Sun Y., Wu Y., Mayers B., Gates B., Yin Y., Kim F., and Yan H. Adv. Mater. 15 (2003) 353-389
28. Acc. Chem. Res. 36 (2002)
29. Chang S.-K., and Hamilton A.D. J. Am. Chem. Soc. 110 (1988) 1318-1319
30. Hager K., Franz A., and Hirsch A. Chem.-Eur. J. 12 (2006) 2663-2679
31. Hager K., Hartnagel U., and Hirsch A. Eur. J. Org. Chem. (2007) 1942-1956
32. Maurer K., Hager K., and Hirsch A. Eur. J. Org. Chem. (2006) 3338-3347
33. Franz A., Bauer W., and Hirsch A. Angew. Chem. 117 (2005) 1588-1591
34. Angew. Chem., Int. Ed. 44 (2005) 1564-1567
35. Wessendorf F., Gnichwitz J.-F., Sarova G.H., Hager K., Hartnagel U., Guldi D.M., and Hirsch A. J. Am. Chem. Soc. 129 (2007) 16057-16071
36. Berl V., Schmutz M., Krische M.J., Khoury R.G., and Lehn J.M. Chem.-Eur. J. 8 (2002) 1227-1244
37. Boyd A.S.F., Carroll J.B., Cooke G., Garety J.F., Jordan B.J., Mabruk S., Rosaira G., and Rotellob V.M. Chem. Commun. (2005) 2468-2470
38. Nagy A., Novak Z., and Kotschy A. J. Organomet. Chem. 690 (2005) 4453-4461
39. Tykwinski R.R. Angew. Chem., Int. Ed. 42 (2003) 1566-1568
40. Littler B.J., Ciringh Y., and Lindsey J.S. J. Org. Chem. 64 (1999) 2864-2872
41. Geier III R.G., and Lindsey J.S. J. Chem. Soc., Perkin Trans. 2 (2001) 677-686
42. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., and Maguerettaz A.M. J. Org. Chem. 52 (1987) 827-836
43. Lindsey J.S., and Wagner R.W. J. Org. Chem. 54 (1989) 828-836
44. Lindsey J.S., MacCrum K.A., Thyonas J.S., and Chuang Y.-Y. J. Org. Chem. 59 (1994) 579-587
45. Sarova G.H., Hartnagel U., Balbinot D., Sali S., Jux N., Hirsch A., and Guldi D.M. Chem.-Eur. J. 14 (2008) 3137-3145
46. Sgobba V., Rahman G.M.A., Guldi D.M., Jux N., Campidelli S., and Prato M. Adv. Mater. 18 (2006) 2264-2269
47. Ehli C., Rahman G.M.A., Jux N., Balbinot, Guldi D.M., Paolucci F., Marcaccio M., Paolucci D., Melle-Franco M., Zerbetto F., Campidelli S., and Prato M. J. Am. Chem. Soc. 128 (2006) 11222-11231
48. Perlmutter-Hayman B. Acc. Chem. Res. 19 (1986) 90-96
49. Schneider H.-J., and Yatsimirsky A. Principles and Methods in Supramolecular Chemistry (2000), Wiley, Chichester, UK
50. Solov'ev, V. P.; Vnuk, E. A.; Strakhova, N. N.; Reavsky, O. A. VINITI, Moscow, 1991;
51. Solov'ev V.P., Baulin V.E., Strahova N.N., Kazachenko V.P., Belsky V.K., Varnek A.A., Volkova T.A., and Wipff G. J. Chem. Soc., Perkin Trans. 1 (1998) 1489-1498
52. Guldi D.M., Zilbermann I., Anderson G., Li A., Balbinot D., Jux N., Hatzimarinaki M., Hirsch A., and Prato M. Chem. Commun. (2004) 726-727
53. Balbinot D., Atalick S., Guldi D.M., Hatzimarinaki M., Hirsch A., and Jux N. J. Phys. Chem. B 107 (2003) 13273-13279
54. Guldi D.M., Rahman G.M.A., Prato M., Jux N., Qin S., and Ford W. Angew. Chem. 117 (2005) 2051-2054
55. Angew. Chem., Int. Ed. 44 (2005) 2015-2018
56. Hirst A.R., Coates I.A., Boucheteau T.R., Miravet J.F., Escuder B., Castelletto V., Hamley I.W., and Smith D.K. J. Am. Chem. Soc. 130 (2008) 9113-9121
57. Martin N., Sanchez L., Herranz M.A., Illescas B., and Guldi D.M. Acc. Chem. Res. 40 (2007) 1015-1024
58. Van der Pol C., Bryce M.R., Wielopolski M., Atienza-Castellanos C., Guldi D.M., Filippone S., and Martin N. J. Org. Chem. 72 (2007) 6662-6671
59. Atienza-Castellanos C., Wielopolski M., Guldi D.M., van der Pol C., Bryce M.R., Filippone S., and Martin N. Chem. Commun. (2007) 5164-5166
60. Atienza C., Martin N., Wielopolski M., Haworth N., Clark T., and Guldi D.M. Chem. Commun. (2006) 3202-3204
61. Perrin D.D., and Amarego W.L.F. Purification of Laboratory Chemicals. 3rd ed. (1988), Pergamon, Oxford