Synthesis, properties, and remarkable 2 D self-assembly at the liquid/solid interface of a series of triskele-shaped 5,11,17-triazatrinaphthylenes (TrisK)

Chemistry - A European Journal

Volumn 19, Issue 43, 2013, Pages 14654-14664

  Bertrand, Hélène ^a   Guillot, Régis ^c   Teulade Fichou, Marie Paule ^b   Fichou, Denis ^a  

^a Université Pierre et Marie Curie   (France)

^b CNRS   (France)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Pi conjugated molecules; polymorphism; scanning tunnelling microscopy; self assembly; triazatrinaphthylenes

Indexed keywords

ABSORPTION AND EMISSION SPECTROSCOPY; CHARGE DENSITY DISTRIBUTIONS; CONJUGATED MOLECULES; LIQUID/SOLID INTERFACE; SELF-ASSEMBLING PROPERTIES; STRUCTURE PROPERTY RELATIONSHIPS; SYNTHETIC PATHWAYS; TRIAZATRINAPHTHYLENES;

CYCLIC VOLTAMMETRY; ELECTRONIC PROPERTIES; EMISSION SPECTROSCOPY; MOLECULES; POLYMORPHISM; SCANNING TUNNELING MICROSCOPY; SELF ASSEMBLY; X RAY DIFFRACTION ANALYSIS;

ORGANIC POLYMERS;

HETEROCYCLIC COMPOUND; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; ELECTROCHEMICAL ANALYSIS; PI-CONJUGATED MOLECULES; POLYMORPHISM; QUANTUM THEORY; SCANNING TUNNELING MICROSCOPY; SCANNING TUNNELLING MICROSCOPY; SELF-ASSEMBLY; SYNTHESIS; TRIAZATRINAPHTHYLENES; X RAY CRYSTALLOGRAPHY;

PI-CONJUGATED MOLECULES; POLYMORPHISM; SCANNING TUNNELLING MICROSCOPY; SELF-ASSEMBLY; TRIAZATRINAPHTHYLENES;

AZA COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMICAL TECHNIQUES; MICROSCOPY, SCANNING TUNNELING; MOLECULAR CONFORMATION; NAPHTHALENES; QUANTUM THEORY;

EID: 84885641259     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300705     Document Type: Article

References (57)

1. J.-M. Lehn, Supramolecular Chemistry, Wiley-VCH, Weinheim, 1995
2. G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418-2421.
3. K. Müllen, J. P. Rabe, Acc. Chem. Res. 2008, 41, 511-520
4. J. Wu, W. Pisula, K. Müllen, Chem. Rev. 2007, 107, 718-747
5. D. Fichou, J. Mater. Chem. 2000, 10, 571-588.
6. Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes, Vol.1 (Eds.:, M. Demeunynck, C. Bailly, W.D. Wilson,), Wiley-VCH, Weinheim, 2003, pp. 178-223.
7. Z. J. Chen, V. Stepanenko, V. Dehm, P. Prins, L. D. A. Siebbeles, J. Seibt, P. Marquetand, V. Engel, F. Würthner, Chem. Eur. J. 2007, 13, 436-449.
8. G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, F. Garnier, Adv. Mater. 1996, 8, 242-245.
9. O. Y. Fedoroff, M. Salazar, H. Y. Han, V. V. Chemeris, S. M. Kerwin, L. H. Hurley, Biochemistry 1998, 37, 12367-12374.
10. X. L. Feng, J. S. Wu, M. Ai, W. Pisula, L. J. Zhi, J. P. Rabe, K. Müllen, Angew. Chem. 2007, 119, 3093-3096
11. Angew. Chem. Int. Ed. 2007, 46, 3033-3036
12. L. Piot, A. Marchenko, J. Wu, K. Müllen, D. Fichou, J. Am. Chem. Soc. 2005, 127, 16245-16250
13. L. Piot, C. Marie, X. Feng, K. Müllen, D. Fichou, Adv. Mater. 2008, 20, 3854-3858
14. L. Piot, C. Marie, X. Dou, X. Feng, K. Müllen, D. Fichou, J. Am. Chem. Soc. 2009, 131, 1378-1379.
15. K. Tahara, S. Furukawa, H. Uji-I, T. Uchino, T. Ichikawa, J. Zhang, W. Mamdouh, M. Sonoda, F. C. DeSchryver, S. DeFeyter, Y. Tobe, J. Am. Chem. Soc. 2006, 128, 16613-16625
16. K. Tahara, C. A. Johnson, T. Fujita, M. Sonoda, F. C. DeSchryver, S. DeFeyter, M. M. Haley, Y. Tobe, Langmuir 2007, 23, 10190-10197.
17. V. Lemaur, D. A. daSilvaFilho, V. Coropceanu, M. Lehmann, Y. Geerts, J. Piris, M. G. Debije, A. M. vandeCraats, K. Senthilkumar, L. D. A. Siebbeles, J. M. Warman, J.-L. Brédas, J. Cornil, J. Am. Chem. Soc. 2004, 126, 3271-3279
18. C. W. Ong, S. C. Liao, T. H. Chang, H. F. Hsu, J. Org. Chem. 2004, 69, 3181-3185
19. M. Lehmann, G. Kestemont, R. G. Aspe, C. Buess-Herman, M. H. Koch, M. G. Debije, J. Piris, M. P. deHaas, J. M. Warman, M. D. Watson, V. Lemaur, J. Cornil, Y. H. Geerts, R. Gearba, D. A. Ivanov, Chem. Eur. J. 2005, 11, 3349-3362
20. S. Sergeyev, W. Pisula, Y. H. Geerts, Chem. Soc. Rev. 2007, 36, 1902-1929.
21. S. Kumar, Liq. Cryst. 2004, 31, 1037-1059
22. F. Charra, J. Cousty, Phys. Rev. Lett. 1998, 80, 1682-1685
23. S. Clair, M. Abel, L. Porte, Angew. Chem. 2010, 122, 8413-8415
24. Angew. Chem. Int. Ed. 2010, 49, 8237-8239
25. N. Katsonis, A. Marchenko, D. Fichou, J. Am. Chem. Soc. 2003, 125, 13682-13683.
26. G. Mahieu, B. Grandidier, D. Stiévenard, C. Krzeminski, C. Delerue, C. Martineau, J. Roncali, Langmuir 2003, 19, 3350-3356.
27. A. L. Kanibolotsky, I. F. Perepichka, P. J. Skabara, Chem. Soc. Rev. 2010, 39, 2695-2728
28. J. M. MacLeod, O. Ivasenko, C. Fu, T. Taerum, F. Rosei, D. F. Perepichka, J. Am. Chem. Soc. 2009, 131, 16844-16850
29. G. J. Su, H. M. Zhang, L. J. Wan. C.-L. Bai, T. Wandlowski, J. Phys. Chem. B 2004, 108, 1931-1937
30. M. Lackinger, S. Griessl, W. M. Heckel, M. Hietschold, G. W. Flynn, Langmuir 2005, 21, 4984-4988
31. J. Liu, X. Zhang, H.-J. Yan, D. Wang, J.-Y. Wang, J. Pei, L. J. Wan, Langmuir 2010, 26, 8195-8200
32. D. Rajwar, X. Sun, S. Cho, A. C. Grimsdale, D. Fichou, CrystEngComm 2012, 14, 5182-5187.
33. N. Saettel, N. Katsonis, A. Marchenko, M.-P. Teulade-Fichou, D. Fichou, J. Mater. Chem. 2005, 15, 3175-3180.
34. H. Bertrand, A. Granzhan, D. Monchaud, N. Saettel, R. Guillot, S. Clifford, A. Guédin, J.-L. Mergny, M.-P. Teulade-Fichou, Chem. Eur. J. 2011, 17, 4529-4539
35. J.-L. Mergny, L. Lacroix, M.-P. Teulade-Fichou, C. Hounsou, L. Guittat, M. Hoarau, P. B. Arimondo, J.-P. Vigneron, J.-M. Lehn, J.-F. Riou, T. Garestier, C. Hélène, Proc. Natl. Acad. Sci. USA 2001, 98, 3062-3067
36. J. T. Davis, Angew. Chem. 2004, 116, 684-716
37. Angew. Chem. Int. Ed. 2004, 43, 668-698.
38. H. Bertrand, F. Silly, M.-P. Teulade-Fichou, L. Tortech, D. Fichou, Chem. Commun. 2011, 47, 10091-10093.
39. S. DeFeyter, F. C. DeSchryver, Chem. Soc. Rev. 2003, 32, 139-150
40. S. J. H. Griessl, M. Lackinger, F. Jamitzsky, T. Markert, M. Hietschold, W. M. Heckl, Langmuir 2004, 20, 9403-9407
41. S. Stepanow, M. Lingenfelder, A. Dmitriev, H. Spillmann, E. Delvigne, N. Lin, X. B. Deng, C. Z. Cai, J. V. Barth, K. Kern, Nat. Mater. 2004, 3, 229-233
42. A. Marchenko, N. Katsonis, D. Fichou, C. Aubert, M. Malacria, J. Am. Chem. Soc. 2002, 124, 9998-9999
43. P. Jiang, A. Nion, A. Marchenko, L. Piot, D. Fichou, J. Am. Chem. Soc. 2006, 128, 12390-12391
44. A. Nion, P. Jiang, A. Popoff, D. Fichou, J. Am. Chem. Soc. 2007, 129, 2450-2451
45. L. Piot, F. Silly, L. Tortech, Y. Nicolas, P. Blanchard, J. Roncali, D. Fichou, J. Am. Chem. Soc. 2009, 131, 12864-12865
46. T. Kudernac, S. Lei, J. A. A. W. Elemans, S. DeFeyter, Chem. Soc. Rev. 2009, 38, 402-421
47. A. Ciesielski, C.-A. Palma, M. Bonini, P. Samori, Adv. Mater. 2010, 22, 3506-3520.
48. R. Lartia, H. Bertrand, M.-P. Teulade-Fichou, Synlett 2006, 0610-0614.
49. G. R. Desiraju, Acc. Chem. Res. 2002, 35, 565-573
50. G. R. Desiraju, Chem. Commun. 2005, 2995-3001.
51. I. Seguy, P. Jolinat, P. Destruel, R. Mamy, H. Allouchi, C. Courseille, M. Cotrait, H. Bock, ChemPhysChem 2001, 2, 448-452.
52. M. Lehmann, V. Lemaur, J. Cornil, J. L. Bredas, S. Goddard, I. Grizzi, Y. Geerts, Tetrahedron 2004, 60, 3283-3291.
53. C. Marie, F. Silly, L. Tortech, K. Müllen, D. Fichou, ACS Nano 2010, 4, 1288-1292.
54. B. Li, Z. Li, J. Yang, J. G. Hou, Chem. Commun. 2011, 47, 2747-2762.
55. J. Repp, G. Meyer, S. M. Stojkovic, A. Gourdon, C. Joachim, Phys. Rev. Lett. 2005, 94, 026803
56. L. Gross, Nat. Chem. 2011, 3, 273-278.
57. Gaussian03, RevisionB.05, M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery,Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.