Soluble conjugated one-dimensional nanowires prepared by topochemical polymerization of a butadiynes-containing star-shaped molecule in the xerogel state

Langmuir

Volumn 29, Issue 10, 2013, Pages 3446-3452

  Néabo, Jules Roméo ^a   Rondeau Gagné, Simon ^a   Vigier Carrieìre, Cécile ^a   Morin, Jean François ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1-D NANOWIRES; DIFFERENT SOLVENTS; ORGANOGEL FORMATION; POLYDIACETYLENES; SELF-ASSEMBLED; STAR-SHAPED MOLECULES; TOPOCHEMICAL POLYMERIZATION; UV IRRADIATION;

MOLECULES; NANOWIRES; STARS; XEROGELS;

ACETYLENE;

EID: 84874906862     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la305045n     Document Type: Article

References (43)

1. Wang, F.; Gillissen, M. A. J.; Stals, P. J. M.; Palmans, A. R. A.; Meijer, E. W. High-Performance, All-Solution-Processed Organic Nanowire Transistor Arrays with Inkjet-Printing Patterned Electrodes Chem.-Eur. J. 2012, 18, 11761-11770
2. Liu, N. L.; Zhou, Y.; Ai, N.; Luo, C.; Peng, J. B.; Wang, J.; Pei, J.; Cao, Y. Hydrogen Bonding Directed Supramolecular Polymerisation of Oligo(Phenylene-Ethynylene)s: Cooperative Mechanism, Core Symmetry Effect and Chiral Amplification Langmuir 2011, 27, 14710-14715
3. Wu, J. H.; Guan, Z. P.; Xu, T. Z.; Xu, Q. H.; Xu, G. Q. Tetracene-Doped Anthracene Nanowire Arrays: Preparation and Doping Effects Langmuir 2011, 27, 6374-6380
4. Feng, X. L.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Towards High Charge-Carrier Mobilities by Rational Design of the Shape and Periphery of Discotics Nat. Mater. 2009, 8, 421-426
5. Hasegawa, M.; Iyoda, M. Conducting Supramolecular Nanofibers and Nanorods Chem. Soc. Rev. 2010, 39, 2420-2427
6. Wu, J. S.; Pisula, W.; Müllen, K. Graphenes as Potential Material for Electronics Chem. Rev. 2007, 107, 718-747
7. Bushey, M. L.; Nguyen, T. Q.; Zhang, W.; Horoszewski, D.; Nuckolls, C. Using Hydrogen Bonds to Direct the Assembly of Crowded Aromatics Angew. Chem., Int. Ed. 2004, 43, 5446-5453
8. Hecht, S.; Khan, A. Intramolecular Cross-Linking of Helical Folds: An Approach to Organic Nanotubes Angew. Chem., Int. Ed. 2003, 42, 6021-6024
9. Harada, A.; Li, J.; Kamachi, M. Synthesis of a Tubular Polymer from Threaded Cyclodextrins Nature 1993, 364, 516-518
10. Yamamoto, T.; Fukushima, T.; Yamamoto, Y.; Kosaka, A.; Jin, W.; Ishii, N.; Aida, T. Stabilization of a Kinetically Favored Nanostructure: Surface ROMP of Self-Assembled Conductive Nanocoils from a Norbornene-Appended Hexa- peri -hexabenzocoronene J. Am. Chem. Soc. 2006, 128, 14337-14340
11. Rondeau-Gagné, S.; Neabo, J. R.; Desroches, M.; Larouche, J.; Brisson, J.; Morin, J.-F. Topochemical Polymerization of Phenylacetylene Macrocycles: a New Strategy for the Preparation of Rigid Organic Nanorods J. Am. Chem. Soc. 2013, 135, 110-113
12. Brand, J. D.; Kubel, C.; Ito, S.; Müllen, K. Functionalized Hexa-peri-hexabenzocoronenes: Stable Supramolecular Order by Polymerization in the Discotic Mesophase Chem. Mater. 2000, 12, 1638-1647
13. Spraul, B. K.; Suresh, S.; Glaser, S.; Perahia, D.; Ballato, J.; Smith, D. W. Perfluorocyclobutyl-Linked Hexa-peri-hexabenzocoronene Networks J. Am. Chem. Soc. 2004, 126, 12772-12773
14. Shirakawa, M.; Fujita, N.; Shinkai, S. A Stable Single Piece of Unimolecularly π-Stacked Porphyrin Aggregate in a Thixotropic Low Molecular Weight Gel: A One-Dimensional Molecular Template for Polydiacetylene Wiring up to Several Tens of Micrometers in Length J. Am. Chem. Soc. 2005, 127, 4164-4165
15. Wegner, G. Topochemical Reactions of Monomers with Conjugated Triple Bonds. I. Polymerization of 2,4-Hexadiyn-1,6-Diols Derivatives in Crystalline State Z Naturforsch. 1969, B24, 824
16. Wegner, G. Topochemical Reactions of Monomers with Conjugated Triple Bonds 0.6. Topochemical Polymerization of Monomers with Conjugated Triple Bonds Makromol. Chem. 1972, 154, 35
17. Ahn, D. J.; Kim, J. M. Fluorogenic Polydiacetylene Supramolecules: Immobilization, Micropatterning, And Application to Label-Free Chemosensors Acc. Chem. Res. 2008, 41, 805-816
18. Lifshitz, Y.; Golan, Y.; Konovalov, O.; Berman, A. Structural Transitions in Polydiacetylene Langmuir Films Langmuir 2009, 25, 4469-4477
19. Ahn, D. J.; Lee, S.; Kim, J. M. Rational Design of Conjugated Polymer Supramolecules with Tunable Colorimetric Responses Adv. Funct. Mater. 2009, 19, 1483-1496
20. Yoon, B.; Lee, S.; Kim, J. M. Recent Conceptual and Technological Advances in Polydiacetylene-Based Supramolecular Chemosensors Chem. Soc. Rev. 2009, 38, 1958-1968
21. Yarimaga, O.; Jaworski, J.; Yoon, B.; Kim, J. M. Polydiacetylenes: Supramolecular Smart Materials with a Structural Hierarchy for Sensing, Imaging and Display Applications Chem. Commun. 2012, 48, 2469-2485
22. Yager, P.; Schoen, P. E. Formation of Tubules by a Polymerizable Surfactant Mol. Cryst. Liq. Cryst. 1984, 106, 371-381
23. Davies, M. A.; Ratna, B. R.; Rudolph, A. S. Structural and Thermodynamic Investigation of Filament Formation in a Diacetylenic Phospholipid Langmuir 1994, 10, 2872-2876
24. Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Lipid Tubule Self-Assembly: Length Dependence on Cooling Rate through a First-Order Phase Transition Science 1995, 267, 1635-1638
25. Masuda, M.; Hanada, T.; Yase, K.; Shimizu, T. Polymerization of Bolaform Butadiyne 1-Glucosamide in Self-Assembled Nanoscale-Fiber Morphology Macromolecules 1998, 31, 9403-9405
26. Spector, M. S.; Selinger, J. V.; Singh, A.; Rodriguez, J. M.; Price, R. R.; Schnur, J. M. Controlling the Morphology of Chiral Lipid Tubules Langmuir 1998, 14, 3493-3500
27. Svenson, S.; Messersmith, P. B. Formation of Polymerizable Phospholipid Nanotubules and Their Transformation into a Network Gel Langmuir 1999, 15, 4464-4471
28. Wang, G.; Hollingsworth, R. I. Easily Accessible Uniform Wide-Diameter Helical, Cylindrical, and Nested Diacetylene Superstructures That Can Be Metallized and Oriented in Magnetic Fields Langmuir 1999, 15, 3062-3069
29. Masuda, M.; Hanada, T.; Okada, Y.; Yase, K.; Shimizu, T. Polymerization in Nanometer-Sized Fibers: Molecular Packing Order and Polymerizability Macromolecules 2000, 33, 9233-9238
30. Tamaoki, N.; Shimada, S.; Okada, Y.; Belaissaoui, A.; Kruk, G.; Yase, K.; Matsuda, H. Polymerization of a Diacetylene Dicholesteryl Ester Having Two Urethanes in Organic Gel States Langmuir 2000, 16, 7545-7547
31. Cheng, Q.; Yamamoto, M.; Stevens, R. C. Amino Acid Terminated Polydiacetylene Lipid Microstructures: Morphology and Chromatic Transition Langmuir 2000, 16, 5333-5342
32. Song, J.; Cheng, Q.; Kopta, S.; Stevens, R. C. Modulating Artificial Membrane Morphology: pH-Induced Chromatic Transition and Nanostructural Transformation of a Bolaamphiphilic Conjugated Polymer from Blue Helical Ribbons to Red Nanofibers J. Am. Chem. Soc. 2001, 123, 3205-3213
33. Gan, H.; Liu, H.; Li, Y.; Zhao, Q.; Li, Y.; Wang, S.; Jiu, T.; Wang, N.; He, X.; Yu, D.; Zhu, D. Fabrication of Polydiacetylene Nanowires by Associated Self-Polymerization and Self-Assembly Processes for Efficient Field Emission Properties J. Am. Chem. Soc. 2005, 127, 12452-12453
34. Zhou, W.; Li, Y.; Zhu, D. Progress in Polydiacetylene Nanowires by Self-Assembly and Self-Polymerization Chem.-Asian J. 2007, 2, 222-229
35. Néabo, J. R.; Tohoundjona, K. I. S.; Morin, J.-F. Topochemical Polymerization of a Diarylbutadiyne Derivative in the Gel and Solid States Org. Lett. 2011, 13, 1358-1361
36. Néabo, J. R.; Vigier-CarrieÌre, C.; Rondeau-Gagné, S.; Morin, J.-F. Room-Temperature Synthesis of Soluble, Fluorescent Carbon Nanoparticles from Organogel Precursors Chem. Commun. 2012, 48, 10144-10146
37. Takahashi, A.; Sakai, M.; Kato, T. Melting Temperature of Thermally Reversible Gel. VI. Effect of Branching on the Sol-Gel Transition of Polyethylene Gels Polym. J. 1980, 12, 335-341
38. Zhang, P.; Wang, H.; Liu, H.; Li, M. Fluorescence-Enhanced Organogels and Mesomorphic Superstructure Based on Hydrazine Derivatives Langmuir 2010, 26, 10183-10190
39. Laschat, S.; Baro, A.; Steinke, N.; Giesselmann, F.; Hägele, C.; Scalia, G.; Judele, R.; Kapatsina, E.; Sauer, S.; Schreivogel, A.; Tosoni, M. Discotic Liquid Crystals: From Tailor-Made Synthesis to Plastic Electronics Angew. Chem., Int. Ed. 2007, 46, 4832-4887
40. Bushey, M. L.; Hwang, A.; Stephens, P. W.; Nuckolls, C. Enforced Stacking in Crowded Arenes J. Am. Chem. Soc. 2001, 123, 8157-8158
41. Palui, G.; Banerjee, A. Fluorescent Gel from a Self-Assembling New Chromophoric Moiety Containing Azobenzene Based Tetraamide J. Phys. Chem. B 2008, 112, 10107-10115
42. Dautel, O. J.; Robitzer, M.; LeÌre-Porte, J.-P.; Serein-Spirau, F.; Moreau, J. J. E. Self-Organized Ureido Substituted Diacetylenic Organogel. Photopolymerization of One-Dimensional Supramolecular Assemblies to Give Conjugated Nanofibers J. Am. Chem. Soc. 2006, 128, 16213-16223
43. Fowler, F. W.; Lauher, J. W. In Carbon-Rich Compounds: From Molecules to Materials; Haley, M. M.; Tykwinski, R. R., Eds.; Wiley-VCH: Weinheim, Germany, 2006.