Trapping Nanostructures on Surfaces through Weak Interactions

Chemistry - A European Journal

Volumn 21, Issue 38, 2015, Pages 13437-13444

  Rauch, Vivien ^a   Kikkawa, Yoshihiro ^b   Koepf, Matthieu ^a   Hijazi, Ismail ^c   Wytko, Jennifer A ^a   Campidelli, Stéphane ^c   Goujon, Antoine ^a   Kanesato, Masatoshi ^b   Weiss, Jean ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^c CEA SACLAY   (France)

Author keywords

nanotubes; porphyrinoids; scanning probe microscopy; self assembly; surface analysis

Indexed keywords

LUNAR SURFACE ANALYSIS; MICA; NANOTUBES; PORPHYRINS; SCANNING PROBE MICROSCOPY; SELF ASSEMBLY; SILICATE MINERALS; SURFACE ANALYSIS; WIRE; YARN; ZINC CASTINGS;

ALKYL DERIVATIVES; HIGHLY ORIENTED PYROLYTIC GRAPHITE; INTERFACIAL ASSEMBLY; METHYLCYCLOHEXANE; NONCOVALENT ASSEMBLIES; PORPHYRINOIDS; SURFACE MOLECULES; THREE-DIMENSIONAL ASSEMBLY;

EVAPORATION;

EID: 84940890577     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501767     Document Type: Article

References (67)

1. For a recent example, see:, J. M. Mativetsky, E. Orgiu, I. Lieberwirth, W. Pisula, P. Samorì, Adv. Mater. 2014, 26, 430-435.
2. F. Klappenberger, M. E. Cañas-Ventura, S. Clair, S. Pons, U. Schlickum, Z.-R. Qu, T. Strunskus, A. Comisso, C. Wöll, H. Brune, K. Kern, A. De Vita, M. Ruben, J. V. Barth, ChemPhysChem. 2008, 9, 2522-2530;
3. T. Chen, G.-B. Pan, H. Wettach, M. Fritzsche, S. Höger, L.-J. Wan, H.-B. Yang, B. H. Northrop, P. J. Stang, J. Am. Chem. Soc. 2010, 132, 1328-1333;
4. A. Datar, D. E. Gross, K. Balakrishnan, X. Yang, J. S. Moore, L. Zang, Chem. Commun. 2012, 48, 8904-8906.
5. L. Grill, M. Dyer, L. Lafferentz, M. Persson, M. V. Peters, Nat. Nanotechnol. 2007, 2, 687;
6. M. Matena, T. Riehm, M. Stöhr, T. A. Jung, L. H. Gade, Angew. Chem. Int. Ed. 2008, 47, 2414-2417;
7. Angew. Chem. 2008, 120, 2448-2451.
8. J. Cai, P. Ruffieux, R. Jaafar, M. Bieri, T. Braun, S. Blankenburg, M. Muoth, A. Seitsonen, M. Saleh, X. Feng, K. Müllen, R. Fasel, Nature 2010, 466, 470-473;
9. M. Koch, M. Gille, A. Viertel, S. Hecht, L. Grill, Surf. Sci. 2014, 627, 70-74.
10. S. Haq, F. Hanke, M. S. Dyer, M. Persson, P. Iavicoli, D. Amabilino, R. Raval, J. Am. Chem. Soc. 2011, 133, 12031-12039;
11. S. Haq, F. Hanke, J. Sharp, M. Persson, D. B. Amabilino, R. Raval, ACS Nano 2014, 8, 8856-8870;
12. H. Zhang, H. Lin, K. Sun, L. Chen, Y. Zagranyarski, N. Aghdassi, S. Duhm, Q. Li, D. Zhong, Y. Li, K. Mullen, H. Fuchs, L. Chi, J. Am. Chem. Soc. 2015, 137, 4022-4025.
13. D. Heim, D. Écija, K. Seufert, W. Auwärter, C. Aurisicchio, C. Fabbro, D. Bonifazi, J. V. Barth, J. Am. Chem. Soc. 2010, 132, 6783-6790;
14. A. Shchyrba, C. Wäckerlin, J. Nowakowski, S. Nowakowska, J. Björk, S. Fatayer, J. Girovsky, T. Nijs, S. C. Martens, A. Kleibert, M. Stöhr, N. Ballav, T. A. Jung, L. H. Gade, J. Am. Chem. Soc. 2014, 136, 9355-9363.
15. M. Koepf, J. Weiss, F. Cherioux, J. A. Wytko, Coord. Chem. Rev. 2012, 256, 2872-2892.
16. M. Jurow, A. E. Schuckman, J. D. Batteas, C. M. Drain, Coord. Chem. Rev. 2010, 254, 2297;
17. S. Sengupta, F. Würthner, Acc. Chem. Res. 2013, 46, 2498-2512.
18. C. M. Drain, A. Varotto, I. Radivojevic, Chem. Rev. 2009, 109, 1630-1658;
19. S. J. Lee, J. T. Hupp, Coord. Chem. Rev. 2006, 250, 1710-1723;
20. I. Beletskaya, V. S. Tyurin, A. Y. Tsivadze, R. Guilard, C. Stern, Chem. Rev. Chem. Rev 2009, 109, 1659-1713;
21. J. A. A. W. Elemans, R. van Hameren, R. J. M. Nolte, A. E. Rowan, Adv. Mater. 2006, 18, 1251-1266.
22. S. Mohnani, D. Bonifazi, Coord. Chem. Rev. 2010, 254, 2342-2362.
23. S. Maier, L.-A. Fendt, L. Zimmerli, T. Glatzel, O. Pfeiffer, F. Diederich, E. Meyer, Small 2008, 4, 1115-1118.
24. L.-A. Fendt, M. Stöhr, N. Wintjes, M. Enache, T. A. Jung, F. Diederich, Chem. Eur. J. 2009, 15, 11139-11150.
25. T. Yokoyama, S. Yokoyama, T. Kamikado, Y. Okuno, S. Mashiko, Nature 2001, 413, 619-621;
26. N. Nagata, S. Kugimiya, E. Fujiwara, Y. Kobuke, New J. Chem. 2003, 27, 743-747.
27. I. Radivojevic, I. Likhtina, X. Shi, S. Singh, C. M. Drain, Chem. Commun. 2010, 46, 1643-1645.
28. A. Satake, M. Fujita, Y. Kurimoto, Y. Kobuke, Chem. Commun. 2009, 1231-1233.
29. A. D. Schwab, D. E. Smith, B. Bond-Watts, D. E. Johnston, J. Hone, A. T. Johnson, J. C. de Paula, W. F. Smith, Nano Lett. 2004, 4, 1261-1265.
30. J. Puigmartí-Luis, A. Minoia, Á. Pérez del Pino, G. Ujaque, C. Rovira, A. Lledõs, R. Lazzaroni, D. B. Amabilino, Chem. Eur. J. 2006, 12, 9161-9175;
31. S. De Feyter, F. C. De Schryver, J. Phys. Chem. A. 2005, 109, 4290-4302;
32. M. M. S. Abdel-Mottaleb, E. Gomar-Nadal, M. Surin, H. Uji-i, W. Mamdouh, J. Veciana, V. Lemaur, C. Rovira, J. Cornil, R. Lazzaroni, D. B. Amabilino, S. De Feyter, F. C. De Schryver, J. Mater. Chem. 2005, 15, 4601-4615.
33. W. Mamdouh, H. Uji-i, J. S. Ladislaw, A. E. Dulcey, V. Percec, F. C. De Schryver, S. De Feyter, J. Am. Chem. Soc. 2006, 128, 317-325;
34. X. Zhang, T. Chen, Q. Chen, G.-J. Deng, Q.-H. Fan, L.-J. Wan, Chem. Eur. J. 2009, 15, 9669-9673;
35. L. Xu, X. Miao, B. Zha, W. Deng, J. Phys. Chem. C 2012, 116, 1061-1069;
36. I. Destoop, H. Xu, C. Oliveras-González, E. Ghijens, D. B. Amabilino, S. De Feyter, Chem. Commun. 2013, 49, 7477-7479;
37. B. Venkataraman, J. J. Breen, G. W. Flynn, J. Phys. Chem. 1995, 99, 6608-6619.
38. Y. Nakagawa, H. Kageyama, Y. Oaki, H. Imai, J. Am. Chem. Soc. 2014, 136, 3716-3719;
39. S. Ahn, A. J. Matzgar, J. Am. Chem. Soc. 2010, 132, 11364-11371;
40. Y. C. Lin, E. J. Petersson, Z. Fakhraai, ACS Nano 2014, 8, 10178-10186.
41. F. Zhang, H.-N. Du, Z.-X. Zhang, L.-N. Ji, H.-T. Li, L. Tang, H.-B. Wang, C.-H. Fan, H.-J. Xu, Y. Zhang, J. Hu, H.-Y. Hu, J.-H. He, Angew. Chem. Int. Ed. 2006, 45, 3611-3613;
42. Angew. Chem. 2006, 118, 3693-3695;
43. J. A. A. W. Elemans, S. Lei, S. De Feyter, Angew. Chem. Int. Ed. 2009, 48, 7298-7332;
44. Angew. Chem. 2009, 121, 7434-7469.
45. J. Brandel, A. Trabolsi, H. Traboulsi, F. Melin, M. Koepf, J. Wytko, M. Elhabiri, J. Weiss, A.-M. Albrecht-Gary, Inorg. Chem. 2009, 48, 3743-3754.
46. D. Paul, F. Melin, C. Hirtz, J. A. Wytko, P. Ochsenbein, M. Bonin, K. Schenk, J. Weiss, Inorg. Chem. 2003, 42, 3779-3787.
47. M. Koepf, J. A. Wytko, J.-P. Bucher, J. Weiss, J. Am. Chem. Soc. 2008, 130, 9994-10001.
48. V. Rauch, J. A. Wytko, M. Takahashi, Y. Kikkawa, M. Kanesato, J. Weiss, Org. Lett. 2012, 14, 1998-2001.
49. X-ray crystallographic data (CIF): CCDC- 1057346 contains the supplementary crystallographic data for this paper. These data are provided free of charge by The Cambridge Crystallographic Data Centre. Single crystals were obtained by slow diffusion of cyclohexane into a solution of the porphyrin in pyridine. Crystallographic data: C71H43N9Zn 4(C5H5N); Mr=1403.91 g mol-1; triclinic, P1 space group; a=12.931(5), b=15.036(5), c=21.650(5) Å; α=97.740(5), β=90.538(5), γ=104.564(5); V=4032.93(8) Å3; T=173(2) K; Z=2, ρcalcd=1.156 g cm-3; 21380 reflections collected, 13548 independent; Rint=0.0559; GooF=1.046; R1=0.0712; wR2=0.1138.
50. T. Haino, Y. Matsumoto, Y. Fukazawa, J. Am. Chem. Soc. 2005, 127, 8936-8937.
51. A. R. Hirst, D. K. Smith, Langmuir 2004, 20, 10851-10857;
52. P. Jonkheijm, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83;
53. G. Zhu, J. S. Dordick, Chem. Mater. 2006, 18, 5988-5995;
54. M. Bielejewski, A. Lapinski, R. Luboradzki, J. Tritt-Goc, Langmuir 2009, 25, 8274-8279;
55. J. Puigmartí-Luis, Á. Pérez del Pino, V. Laukhin, L. N. Feldborg, C. Rovira, E. Laukhina, D. B. Amabilino, J. Mater. Chem. 2010, 20, 466-474;
56. S. Leiras, F. Freire, E. Quiñoá, R. Riguera, Chem. Sci. 2015, 6, 246-253.
57. V. Rauch, J. Conradt, M. Takahashi, M. Kanesato, J. A. Wytko, Y. Kikkawa, H. Kalt, J. Weiss, J. Porphyrins Phthalocyanines 2014, 18, 67-75.
58. I. Leray, B. Valeur, D. Paul, E. Regnier, M. Koepf, J. A. Wytko, C. Boudon, J. Weiss, Photochem. Photobiol. Sci. 2005, 4, 280-286.
59. J. K. Sprafke, S. D. Stranks, J. H. Warner, R. J. Nicholas, H. L. Anderson, Angew. Chem. Int. Ed. 2011, 50, 2313-2316;
60. Angew. Chem. 2011, 123, 2361-2364;
61. S. D. Stranks, J. K. Sprafke, H. L. Anderson, R. J. Nicholas, ACS Nano 2011, 5, 2307-2315.
62. F. Cheng, A. Adronov, Chem. Eur. J. 2006, 12, 5053-5059.
63. Y. Tomonari, H. Murakami, N. Nakashima, Chem. Eur. J. 2006, 12, 4027-4034;
64. Y.-L. Zhao, J. F. Stoddart, Acc. Chem. Res. 2009, 42, 1161-1171;
65. H. Murakami, T. Nomura, N. Nakashima, Chem. Phys. Lett. 2003, 378, 481;
66. G. Gavrel, B. Jousselme, A. Filoramo, and, S. Campidelli, in Making and Exploiting Fullerenes, Graphene, and Carbon Nanotubes, Vol. 348 (Eds. , M. Marcaccio, F. Paolucci,), Springer, Berlin, 2014, pp. 95-126.
67. T. Palacin, H. Le Khanh, B. Jousselme, P. Jegou, A. Filoramo, C. Ehli, D. M. Guldi, S. Campidelli, J. Am. Chem. Soc. 2009, 131, 15394-15402.