Directed assembly of optoelectronically active alkyl-π-conjugated molecules by adding n-alkanes or π-conjugated species

Nature Chemistry

Volumn 6, Issue 8, 2014, Pages 690-696

  Hollamby, Martin J ^a,b   Karny, Maciej ^c   Bomans, Paul H H ^d   Sommerdjik, Nico A J M ^d   Saeki, Akinori ^e   Seki, Shu ^e   Minamikawa, Hiroyuki ^f   Grillo, Isabelle ^g   Pauw, Brian R ^a   Brown, Paul ^h   Eastoe, Julian ^h   Möhwald, Helmuth ⁱ   Nakanishi, Takashi ^a,c  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b KEELE UNIVERSITY   (United Kingdom)

^c WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^d EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^e OSAKA UNIVERSITY   (Japan)

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

^g INSTITUT LAUE LANGEVIN   (France)

^h UNIVERSITY OF BRISTOL   (United Kingdom)

ⁱ MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL PHENOMENA; CHEMISTRY; MICELLE; THERMODYNAMICS;

ALKANES; FULLERENES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICELLES; THERMODYNAMICS;

EID: 84904791285     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1977     Document Type: Article

References (50)

1. Rothemund, P. W. K. Folding DNA to create nanoscale shapes and patterns. Nature 440, 297-302 (2006
2. Sobczak, J-P. J., Martin, T. G., Gerling, T. & Dietz, H. Rapid folding of DNA into nanoscale shapes at constant temperature. Science 338, 1458-1461 (2012
3. Aida, T., Meijer, E. W. & Stupp, S. I. Functional supramolecular polymers. Science 335, 813-817 (2012
4. Du, G., Moulin, E., Jouault, N., Buhler, E. & Giuseppone, N. Muscle-like supramolecular polymers: integrated motion from thousands of molecular machines. Angew. Chem. Int. Ed. 51, 12504-12508 (2012
5. Wang, C., Wang, Z. & Zhang, X. Amphiphilic building blocks for self-assembly: from amphiphiles to supra-amphiphiles. Acc. Chem. Res. 45, 608-618 (2012
6. Israelachvili, J. in Surfactants in Solution (eds Mittal, K. L. & Bothorel, P.) 3-33 (Springer, 1987
7. Altoe, V., Martin, F., Katan, A., Salmeron, M. & Aloni, S. Electron microscopy reveals structure and morphology of one molecule thin organic films. Nano Lett. 12, 1295-1299 (2012
8. Henson, Z. B., Müllen, K. & Bazan, G. C. Design strategies for organic semiconductors beyond the molecular formula. Nature Chem. 4, 699-704 (2012
9. Pisula, W., Feng, X. & Müllen, K. Tuning the columnar organization of discotic polycyclic aromatic hydrocarbons. Adv. Mater. 22, 3634-3649 (2010
10. Percec, V. et al. Self-organization of supramolecular helical dendrimers into complex electronic materials. Nature 419, 384-387 (2002
11. Saez, I. M. & Goodby, J. W. Supermolecular liquid crystals. J. Mater. Chem. 15, 26-40 (2005
12. Guillon, D., Donnio, B. & Deschenaux, R. in Supramolecular Chemistry of Fullerenes and Carbon Nanotubes (eds Martín, N. & Nierengarten, J-F.) 203-235 (Wiley-VCH, 2012
13. Binks, B. P., Fletcher, P. D. I., Kotsev, S. N. & Thompson, R. L. Adsorption and aggregation of semifluorinated alkanes in binary and ternary mixtures with hydrocarbon and fluorocarbon solvents. Langmuir 13, 6669-6682 (1997
14. Blanazs, A., Armes, S. P. & Ryan, A. J. Self-assembled block copolymer aggregates: from micelles to vesicles and their biological applications. Macromol. Rapid Commun. 30, 267-277 (2009
15. Nakanishi, T. Supramolecular soft and hard materials based on selfassembly algorithms of alkyl-conjugated fullerenes. Chem. Commun. 46, 3425-3436 (2010
16. Li, H. et al. Alkylated-C60 based soft materials: regulation of self-assembly and optoelectronic properties by chain branching. J. Mater. Chem. C 1, 1943-1951 (2013
17. Vergara, J. et al. Liquid-crystalline hybrid materials based on [60]fullerene and bent-core structures. Angew. Chem. Int. Ed. 50, 12523-12528 (2011
18. Li, H., Choi, J. & Nakanishi, T. Optoelectronic functional materials based on alkylated-π molecules: self-assembled architectures and nonassembled liquids. Langmuir 29, 5394-5406 (2013
19. Zhong, Y-W., Matsuo, Y. & Nakamura, E. Lamellar assembly of conical molecules possessing a fullerene apex in crystals and liquid crystals. J. Am. Chem. Soc. 129, 3052-3053 (2007
20. Ruoff, R. S., Tse, D. S., Malhotra, R. & Lorents, D. C. Solubility of fullerene (C60) in a variety of solvents. J. Phys. Chem. 97, 3379-3383 (1993
21. Kordatos, K., Da Ros, T., Prato, M., Bensasson, R. V. & Leach, S. Absorption spectra of the mono-adduct and eight bis-adduct regioisomers of pyrrolidine derivatives of C60. Chem. Phys. 293, 263-280 (2003
22. Sedov, I. A., Stolov, M. A. & Solomonov, B. N. Solvophobic effects and relationships between the Gibbs energy and enthalpy for the solvation process. J. Phys. Org. Chem. 24, 1088-1094 (2011
23. Moyá, M. L., Rodríguez, A., Graciani, M. del M. & Fernández, G. Role of the solvophobic effect on micellization. J. Colloid Interface Sci. 316, 787-795 (2007
24. Hollamby, M. J. Practical applications of small-angle neutron scattering. Phys. Chem. Chem. Phys. 15, 10566-10579 (2013
25. Guinier, A. La diffraction des rayons X aux tres petits angles: Application a l'étude de phénomenes ultramicroscopiques. Ann. Phys. 12, 161-237 (1939
26. Hyde, S. T. in Handbook of Applied Surface and Colloid Chemistry Vol. 1-2, 299-332 (Wiley, 2001
27. Ishi-i, T., Ono, Y. & Shinkai, S. Chirally-ordered fullerene assemblies found in organic gel systems of cholesterol-appended [60]fullerenes. Chem. Lett. 29, 808-809 (2000
28. Yang, X. et al. Self-assembly of a new C60 compound with an L-glutamid-derived lipid unit: formation of organogels and hierarchically structured spherical particles. Soft Matter 7, 3592-3598 (2011
29. Newbloom, G. M., Kim, F. S., Jenekhe, S. A. & Pozzo, D. C. Mesoscale morphology and charge transport in colloidal networks of poly(3-hexylthiophene). Macromolecules 44, 3801-3809 (2011
30. Saeki, A., Seki, S., Takenobu, T., Iwasa, Y. & Tagawa, S. Mobility and dynamics of charge carriers in rubrene single crystals studied by flash-photolysis microwave conductivity and optical spectroscopy. Adv. Mater. 20, 920-923 (2008
31. Babu, S. S., Saeki, A., Seki, S., Möhwald, H. & Nakanishi, T. Millimeter-sized flat crystalline sheet architectures of fullerene assemblies with anisotropic photoconductivity. Phys. Chem. Chem. Phys. 13, 4830-4834 (2011
32. Zhang, X. et al. Flowerlike supramolecular architectures assembled from C60 equipped with a pyridine substituent. Chem. Commun. 46, 8752-8754 (2010
33. Babu, S. S., Prasanthkumar, S. & Ajayaghosh, A. Self-assembled gelators for organic electronics. Angew. Chem. Int. Ed. 51, 1766-1776 (2012
34. Park, C., Song, H. J. & Choi, H. C. The critical effect of solvent geometry on the determination of fullerene (C60) self-assembly into dot, wire and disk structures. Chem. Commun. 4803-4805 (2009
35. Lei, T. & Pei, J. Solution-processed organic nano-and micro-materials: design strategy, growth mechanism and applications. J. Mater. Chem. 22, 785-798 (2012
36. Vera, F. et al. Microstructured objects produced by the supramolecular hierarchical assembly of an organic free radical gathering hydrophobic- amphiphilic characteristics. Chem. Sci. 3, 1958-1962 (2012
37. Sathish, M., Miyazawa, K., Hill, J. P. & Ariga, K. Solvent engineering for shapeshifter pure fullerene (C60). J. Am. Chem. Soc. 131, 6372-6373 (2009
38. Balakrishnan, K. et al. Effect of side-chain substituents on self-assembly of perylene diimide molecules: morphology control. J. Am. Chem. Soc. 128, 7390-7398 (2006
39. Hollamby, M. J. et al. Tri-chain hydrocarbon surfactants as designed micellar modifiers for supercritical CO2. Angew. Chem. Int. Ed. 48, 4993-4995 (2009
40. Ryoo, W., Webber, S. E. & Johnston, K. P. Water-in-carbon dioxide microemulsions with methylated branched hydrocarbon surfactants. Ind. Eng. Chem. Res. 42, 6348-6358 (2003
41. Nurmawati, M. H., Ajikumar, P. K., Renu, R., Sow, C. H. & Valiyaveettil, S. Amphiphilic poly( p-phenylene)-driven multiscale assembly of fullerenes to nanowhiskers. ACS Nano 2, 1429-1436 (2008
42. Kawauchi, T. et al. Encapsulation of fullerenes in a helical PMMA cavity leading to a robust processable complex with a macromolecular helicity memory. Angew. Chem. Int. Ed. 47, 515-519 (2008
43. Tashiro, K. & Aida, T. Metalloporphyrin hosts for supramolecular chemistry of fullerenes. Chem. Soc. Rev. 36, 189-197 (2007
44. Giacalone, F. & Martín, N. New concepts and applications in the macromolecular chemistry of fullerenes. Adv. Mater. 22, 4220-4248 (2010
45. Patterson, A. L. The Scherrer formula for X-ray particle size determination. Phys. Rev. 56, 978 (1939
46. Hirata, S. et al. Improvement of electroluminescence performance of organic light-emitting diodes with a liquid-emitting layer by introduction of electrolyte and a hole-blocking layer. Adv. Mater. 23, 889-893 (2011
47. Babu, S. S. et al. Nonvolatile liquid anthracenes for facile full-colour luminescence tuning at single blue-light excitation. Nature Commun. 4, 1969 (2013
48. Burghardt, S., Hirsch, A., Schade, B., Ludwig, K. & Böttcher, C. Switchable supramolecular organization of structurally defined micelles based on an amphiphilic fullerene. Angew. Chem. Int. Ed. 44, 2976-2979 (2005
49. Nierengarten, J.-F. Chemical modification of C60 for materials science applications. New J. Chem. 28, 1177-1191 (2004
50. Zhao, C. et al. Do deuteriums form stronger CH-π interactions? J. Am. Chem. Soc. 134, 14306-14309 (2012).