Dipole-controlled self-assembly of 2,7-Bis(n-alkoxy)-9-fluorenone: Odd-even and chain-length effects

Journal of Physical Chemistry C

Volumn 117, Issue 24, 2013, Pages 12707-12714

  Xu, Li ^a   Miao, Xinrui ^a   Zha, Bao ^a   Miao, Kai ^a   Deng, Wenli ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL METHOD; CHEMICAL HOMOGENEITY; EVEN-ODD EFFECT; HIGHLY ORIENTED PYROLYTIC GRAPHITE; LAMELLAR PATTERNS; SELF-ASSEMBLED; SELF-ASSEMBLED PATTERNS; ZIG-ZAG STRUCTURES;

CHEMICAL ANALYSIS; DICHLOROMETHANE; FUNCTIONAL GROUPS; KETONES; SCANNING TUNNELING MICROSCOPY; TOOLS;

SELF ASSEMBLY;

EID: 84879423286     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp403881t     Document Type: Article

References (31)

1. Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics Using Hybrid-Molecular and Mono-Molecular Devices Nature 2000, 408, 541-548
2. Schwab, M. G.; Qin, T.; Pisula, W.; Mavrinskiy, A.; Feng, X.; Baumgarten, M.; Kim, H.; Laquai, F.; Schuh, S.; Trattnig, R.; List, E. J. W.; Müllen, K. Molecular Triangles: Synthesis, Self-Assembly, and Blue Emission of Cyclo-7,10-tris-triphenylenyl Macrocycles Chem.-Asia J. 2011, 6, 3001-3010
3. Xue, Y.; Zimmt, M. B. Tetris in Monolayers: Patterned Self-Assembly Using Side Chain Shape Chem. Commun. 2011, 47, 8832-8834
4. Tahara, K.; Yamaga, H.; Ghijsens, E.; Inukai, K.; Adisoejoso, J.; Blunt, M. O.; De Feyter, S.; Tobe, Y. Control and Induction of Surface-Confined Homochiral Porous Molecular Networks Nat. Chem. 2011, 3, 714-719
5. Miao, X.; Xu, L.; Li, Y.; Li, Z.; Zhou, J.; Deng, W. Tuning the Packing Density of Host Molecular Self-Assemblies at the Solid-Liquid Interface Using Guest Molecule Chem. Commun. 2010, 46, 8830-8832
6. Jewell, A. D.; Kyran, S. J.; Rabinovich, D.; Sykes, E. C. H. Effect of Head-Group Chemistry on Surface-Mediated Molecular Self-Assembly Chem.-Eur. J. 2012, 18, 7169-7178
7. Jester, S.-S.; Sigmund, E.; Röck, L. M.; Höger, S. Hierarchical Self-Assembly of Polycyclic Heteroaromatic Stars into Snowflake Patterns Angew. Chem., Int. Ed. 2012, 51, 8555-8559
8. Tao, F.; Bernasek, S. L. Understanding Odd-Even Effects in Organic Self-Assembled Monolayers Chem. Rev. 2007, 107, 1408-1453
9. Hibino, M.; Sumi, A.; Tsuchiya, H.; Hatta, I. Microscopic Origin of the Odd-Even Effect in Monolayer of Fatty Acids Formed on a Graphite Surface by Scanning Tunneling Microscopy J. Phys. Chem. B 1998, 102, 4544-4547
10. Tao, F.; Goswami, J.; Bernasek, S. L. Self-Sssembly and Odd-Even Effects of Cis-unsaturated Carboxylic Acids on Highly Oriented Pyrolytic Graphite J. Phys. Chem. B 2006, 110, 4199-4206
11. Yablon, D. G.; Wintgens, D.; Flynn, G. W. Odd/Even Effect in Self-Assembly of Chiral Molecules at the Liquid-Solid Interface: An STM Investigation of Coadsorbate Control of Self-Assembly J. Phys. Chem. B 2002, 106, 5470-5475
12. Thomas, L. K.; Kühnle, A.; Rode, S.; Beginn, U.; Reichling, M. Monolayer Structure of Arachidic Acid on Graphite J. Phys. Chem. C 2010, 114, 18919-18924
13. Schneider, J.; Messerschmidt, C.; Schulz, A.; Gnade, M.; Schade, B.; Luger, P.; Bombicz, P.; Hubert, V.; Fuhrhop, J.-H. Odd-Even Effects in Supramolecular Assemblies of Diamide Bolaamphiphiles Langmuir 2000, 16, 8575-8584
14. Jonkheijm, P.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Probing the Solvent-Assisted Nucleation Pathway in Chemical Self-Assembly Science 2006, 313, 80-83
15. Wei, Y. H.; Kannappan, K.; Flynn, G. W.; Zimmt, M. B. Scanning Tunneling Microscopy of Prochiral Anthracene Derivatives on Graphite: Chain Length Effects on Monolayer Morphology J. Am. Chem. Soc. 2004, 126, 5318-5322
16. Kikkawa, Y.; Koyama, E.; Tsuzuki, S.; Fujiwara, K.; Kanesato, M. Bipyridine Derivatives at a Solid/Liquid Interface: Effects of the Number and Length of Peripheral Alkyl Chains Langmuir 2010, 26, 3376-3381
17. Xu, L.; Miao, X. R.; Ying, X.; Deng, W. L. Two-Dimensional Self-Assembled Molecular Structures Formed by the Competition of van der Waals Forces and Dipole-Dipole Interactions J. Phys. Chem. C 2012, 116, 1061-1069
18. Xu, L.; Miao, X.; Zha, B.; Deng, W. Self-Assembly Polymorphism: Solvent-Responsive 2D Morphologies of 2,7-Ditridecyloxy-9-Fluorenone by Scanning Tunneling Microscopy J. Phys. Chem. C 2012, 116, 16014-16022
19. Miao, X. R.; Xu, L.; Li, Z. M.; Deng, W. L. Solvent-Induced Structural Transitions of a 1,3,5-Tris(10-ethoxycarbonyldecyloxy)benzene Assembly Revealed by Scanning Tunneling Microscopy J. Phys. Chem. C 2011, 115, 3358-3367
20. Mamdouh, W.; Uji-i, H.; Ladislaw, J. S.; Dulcey, A. E.; Percec, V.; De Schryver, F. C.; De Feyter, S. Solvent Controlled Self-Assembly at the Liquid-Solid Interface Revealed by STM J. Am. Chem. Soc. 2006, 128, 317-325
21. Shao, X.; Luo, X. C.; Hu, X. Q.; Wu, K. Solvent Effect on Self-Assembled Structures of 3,8-Bis-hexadecyloxy-benzo[c]cinnoline on Highly Oriented Pyrolytic Graphite J. Phys. Chem. B 2006, 110, 1288-1293
22. Takami, T.; Mazur, U.; Hipps, K. W. Solvent-Induced Variations in Surface Structure of a 2,9,16,23-Tetra-tert-butyl-phthalocyanine on Graphite J. Phys. Chem. C 2009, 113, 17479-17483
23. Yang, Y. L.; Wang, C. Solvent Effects on Two-Dimensional Molecular Self-Assemblies Investigated by Using Scanning Tunneling Microscopy Curr. Opin. Colloid Interface Sci. 2009, 14, 135-147
24. Ivanov, A. V.; Lyakhov, S. A.; Yarkova, M. Y.; Galatina, A. I.; Mazepa, A. V. Synthesis and Liquid Crystal Properties of 2,7-Dialkoxy-9-fluorenones Russ. J. Gen. Chem. 2002, 72, 1435-1438
25. T. Imrie, C.; R. Luckhurst, G. Liquid Crystal Trimers. The Synthesis and Characterisation of the 4,4[prime or minute]-bis[[small omega]-(4-cyanobiphenyl- 4[prime or minute]-yloxy)alkoxy]biphenyls J. Mater. Chem. 1998, 8, 1339-1343
26. Pardey, R.; Zhang, A.; Gabori, P. A.; Harris, F. W.; Cheng, S. Z. D.; Adduci, J.; Facinelli, J. V.; Lenz, R. W. Monotropic Liquid Crystal Behavior in Two Poly(ester imides) with Even and Odd Flexible Spacers Macromolecules 1992, 25, 5060-5068
27. Wiederrecht, G. P.; Yoon, B. A.; Wasielewski, M. R. High Photorefractive Gain in Nematic Liquid Crystals Doped with Electron Donor and Acceptor Molecules Science 1995, 270, 1794-1797
28. Miyake, Y.; Nagata, T.; Tanaka, H.; Yamazaki, M.; Ohta, M.; Kokawa, R.; Ogawa, T. Entropy-Controlled 2D Supramolecular Structures of N,N′-Bis(n-alkyl)naphthalenediimides on a HOPG Surface ACS Nano 2012, 3867-3887
29. Florio, G. M.; Werblowsky, T. L.; Ilan, B.; Müller, T.; Berne, B. J.; Flynn, G. W. Chain-Length Effects on the Self-Assembly of Short 1-Bromoalkane and n-Alkane Monolayers on Graphite J Phys. Chem. C 2008, 112, 18067-18075
30. Zang, L.; Che, Y.; Moore, J. S. One-Dimensional Self-Assembly of Planar π-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices Acc. Chem. Res. 2008, 41, 1596-1608
31. Kampschulte, L.; Lackinger, M.; Maier, A. K.; Kishore, R. S. K.; Griessl, S.; Schmittel, M.; Heckl, W. M. Solvent Induced Polymorphism in Supramolecular 1,3,5-Benzenetribenzoic Acid Monolayers J Phys. Chem. B 2006, 110, 10829-10836