Ordered architectures of a soluble hexa-peri-hexabenzocoronene-pyrene dyad: Thermotropic bulk properties and nanoscale phase segregation at surfaces

Journal of the American Chemical Society

Volumn 125, Issue 32, 2003, Pages 9734-9739

  Tchebotareva, Natalia ^a   Yin, Xiaomin ^b   Watson, Mark D ^a   Samorì, Paolo ^b,c   Rabe, Jürgen P ^b   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

^c Istituto Per La Sintesi Organica E La Fotoreattività   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DIFFERENTIAL SCANNING CALORIMETRY; LIGHT POLARIZATION; MOLECULAR STRUCTURE; SELF ASSEMBLY; THERMOTROPIC LIQUID CRYSTALS; X RAY SCATTERING;

HOMEOTROPIC ALIGNMENT;

ORGANIC COMPOUNDS;

BENZENE DERIVATIVE; NANOPARTICLE; PYRENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; ELECTRON TRANSPORT; ELECTRONICS; MICROSCOPY; MOLECULAR DYNAMICS; POLARIZATION; RADIATION SCATTERING; ROOM TEMPERATURE; SYNTHESIS;

EID: 0043127092     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028609i     Document Type: Article

References (47)

1. Lehn, J. M. Science 2002, 29, 2400-2403.
2. Watson, M. D.; Fechtenkotter A.; Müllen K. Chem. Rev. 2001, 101, 1267-1300.
3. (a) Clar, E. The Aromatic Sextet; John Wiley: London, 1972.
4. (b) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123-1146; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101-1123.
5. (b) Diederich, F.; Rubin, Y. Angew. Chem. 1992, 104, 1123-1146; Angew. Chem., Int. Ed. Engl. 1992, 31, 1101-1123.
6. (c) Adam, D.; Schuhmacher, P.; Simmerer, J.; Häussling, L.; Siemensmeyer, K.; Etzbach, K. H.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141-143.
7. (d) Faust, R. Angew. Chem. 1995, 107, 1559-1562; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-1432.
8. (d) Faust, R. Angew. Chem. 1995, 107, 1559-1562; Angew. Chem., Int. Ed. Engl. 1995, 34, 1429-1432.
9. (e) Hudgins, D. M.; Allamandola, L. J. J. Phys. Chem. 1995.99, 3033-3046.
10. (f) Scott, L. T.; Cheng, P.-C.; Hashemi, M.M.,; Bratcher, M. S.; Meyer, D. T.; Warren, H. B. J. Am, Chem. Soc. 1997, 119, 10963-10968.
11. (g) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120,. 6000-6006.
12. (h) Debad, J. D.; Bard, A. J. J. Am. Chem. Soc. 1998, 120, 2476-2477.
13. (i) Draper, S. M.; Gregg, D. J.; Madathil, R. J. Am. Chem. Soc. 2002, 124, 3486-3487.
14. (a) Stabel, A.; Herwig, P.; Müllen, K.; Rabe, J. P. Angew. Chem., Int. Ed. Engl 1995, 34, 1609.
15. (b) van de Craats, A. M.; Warman, J. M. Adv. Mater. 2001, 13, I30 130-133.
16. Schmidt-Mende, L.; Fechtenkötter A.; Müllen K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1123.
17. (a) Ito, S.; Wehmeier, M.; Brand, J. D.; Kübel C.; Epsch, R.; Rabe, J. P.; Müllen K. Chem. Eur. J. 2000, 6, 4327-4342.
18. (b) Grimsdale, A. C.; Bauerr, R.; Weil, T.; Tchebotareva, N.; Wu, J.; Watson, M.; Müllen, K. Synthesis-Stuttgart 2002, 9, 1229-38.
19. (a) Eckert, J.-F.; Nicoud, J.-F.; Nierengarten, J.-F.; Liu, S.-G.; Echegoyen, L.; Armaroli, N.; Barigelletti, F.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. J. Am. Chem. Soc 2000, 122. 7467-7479.
20. (b) Cravino, A.; Sariciftci N. S. J. Mater. Chem. 2002, 12, 1931-1943.
21. (c) Pourtois, G.; Beljonne, D.; Cornil, J.; Ratner, M. A.;: Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 4436-4447.
22. Fechtenkötter A.; Tchebotareva, N.: Watson. M. D.: Müllen, K. Tetrahedron 2001, 57, 3769-3783.
23. (a) Bunk, O.: Nielsen, M. M.; SoØlling, T. L; van de Craats A. M.: Stutzmann, N.; J. Am. Chem. Soc. 2003, 125, 2252-2258.
24. (b) van de Craats, A. M.; Stutzmann, N.; Bunk, O.; Nielsen M. M.; Watson, M. D.; Müllen, K.; Chanzy, H. D.; Sirringhaus, H.; Friend, R. H. Adv. Mater. 2003, 15, 495-99.
25. Kettner, A.; Wendorff, J. H. Liq. Cryst. 1999, 26, 483-487.
26. Supporting Information: (a) 2D WAXS diffractrograms and their integrations; (b) tabulated reflexes and Miller indices; (c) optical micrograph of homeotropically aligned thin film of 1; (d) survey (large-area) STM image of 1 at the graphite/solution interface
27. Chandrasekhar, S.; Sadashiva, B. K.; Surish, K. A. Pramana 1977, 9, 471-480.
28. Hazel, A. C.; Larsen, F. K.; Lehmann M. S. Acta Crystallogr., Sect. B 1972, B28, 2977-2984.
29. (a) Kroon, J. M.; Koehorst R. B. M.; van Dijk, M.; Sanders, G. M, Sudhölter, E. J. R. J. Mater. Chem 1997, 7, 615-624.
30. (b) Hatsusaka, K.; Ohto, K. Yamamoto, I. Shirai, H. J. Mater. Chem. 2001, 11, 423-433.
31. (c) Jung, H. T.; Kim, S. O.; Ko, Y, K.; Yoon, D. K.; Hudson, S. D.; Percec, V.; Holerca, M. N.; Cho, W. D.; Mosier, P. E. Macromolecules 2002, 35, 3717-3721.
32. (a) Gimzewski J. K.; Joachim C. Science 1999, 283. 1683-1688.
33. (b) Yazdani, A.,; Lieber, C. M. Nature 1999, 401, 227-230.
34. (a) McGonigal G. C.; Bernhardt, R. H.: Thomson, D. J. Appl. Phys. Lett. 1990, 57. 28-30.
35. (b) Rabe. J. P.: Buchholz, S. Science 1991, 253, 424-427.
36. (c) Cyr, D. M.; Venkataraman, B.; Flynn, G. W. Chem. Mater. 1996, 8. 1600-1615.
37. (d) Claypool, C. L.; Faglioni, F.; Goddard, W. A., III; Gray, H. B.; Lewis, N.; Marcus, R. A. J. Phys. Chem. B 1997, 1O1, 5978-5995.
38. (e) Qiu, X.; Wang, C.: Zeng, Q.; Xu. B.; Yin, S.; Wang, H.: Xu, S.; Bai, C. J. Am. Chem. Soc. 2000, 122, 5550-5556.
39. (f) Gesquière A.; Abdel-Mottaleb, M. M. S,; De Feyter, S.: De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L.; Calderone, A.; Lazzaroni, R.; Brédas, J. L. Lamgmuir 2000, 16, 10385-10391.
40. (g) Isoda, S.; Nemoto, T.: Fujiwara, E.; Adachi, Y.; Kobayashi, T. J. Coyst. Growth 2001, 229, 574-579.
41. Samorí P.; Fechtenkötter, A.; Böhme T.; Jäckel, F. ; Müllen K.; Rabe J. P. J. Aro. Chem Soc. 2001, 123, 11462-11467.
42. Lazzaroni, R,; Calderone, A.; Brédas, J. L.; Rabe, J. P. J. Chem. Phys, 1997, 107, 99-105.
43. By changing the STM tip and varying the scanning direction through imaging differently oriented domains, we could rule out imaging artifacts during the measurements.
44. Strohmaier, R.; Petersen, J.; Gompf, B.; Eisenmenger W. Surf. Sci. 1998, 418, 91 -104.
45. Fischbach, I.; Pakula, T.; Minkin, P.; Fechtenkötter, A.; Müllen, K.; Spiess, H. W.; Saalwächter K. J. Phys. Chem. B 2002, 106, 6408-18.
46. Hillner P. E.; Wolf, J. F.; Rabe. J. P. Humboldt University Berlin.
47. Scanning Probe Image Processor, version 1.72, Image Metrology ApS, Lyngby, Denmark.