Aqueous self-sorting in extended supramolecular aggregates

International Journal of Molecular Sciences

Volumn 14, Issue 1, 2013, Pages 1541-1565

  Rest, Christina ^a   Mayoral, María José ^a   Fernández, Gustavo ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Co aggregation; Self assembly; Self sorting; Supramolecular chemistry

Indexed keywords

SOLVENT; WATER; MACROMOLECULE;

CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONCENTRATION RESPONSE; GEL; HYDROGEN BOND; HYDROPHOBICITY; LIGHT SCATTERING; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; PARTICLE SIZE; REVIEW; SELF ORGANIZATION; SELF SORTING; STATIC ELECTRICITY; SUPRAMOLECULAR CHEMISTRY; SURFACE CHARGE; SYSTEMS BIOLOGY; TRANSMISSION ELECTRON MICROSCOPY; CHEMICAL MODEL; CHEMICAL PHENOMENA; CHEMISTRY; CONFORMATION; MACROMOLECULE; ULTRASTRUCTURE;

CHEMICAL PHENOMENA; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MACROMOLECULAR SUBSTANCES; MICROSCOPY, ELECTRON, TRANSMISSION; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; WATER;

EID: 84878632068     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms14011541     Document Type: Review

References (47)

1. Oshovsky, G.V.; Reinhoudt, D.N.; Verboom, W. Supramolecular Chemistry in Water. Angew. Chem. Int. Ed. 2007, 46, 2366-2393.
2. Lehninger, A.L.; Nelson, D.L.; Cox, M.M. Lehninger Principles of Biochemistry, 5th Ed.; W.H. Freeman & Company: New York, NY, USA, 2008.
3. Hübscher, U.; Maga, G. DNA replication and repair bypass machines. Curr. Opin. Chem. Biol. 2011, 15, 627-635.
4. Amos, L.A.; Baker, T.S. The three-dimensional Structure of Tubulin Protofilaments. Nature 1979, 279, 607-612.
5. Desai, A.; Mitchison, T.J. Microtubule Polymerization Dynamics. Annu. Rev. Cell Dev. Biol. 1997, 13, 83-117.
6. Weisenberg, R.C. Microtubule Formation in vitro in Solutions Containing Low Calcium Concentrations. Science 1972, 177, 1104-1105.
7. Ariga, K.; Hill, J.P.; Lee, M.V.; Vinu, A.; Charvet, R.; Acharya, S. Challenges and breakthroughs in recent research on self-assembly. Sci. Technol. Adv. Mater. 2008, 9, 014109:1-014109:96.
8. Ludlow, R.F.; Otto, S. Systems Chemistry. Chem. Soc. Rev. 2008, 37, 101-108.
9. Safont-Sempere, M.M.; Fernandez, G.; Würthner, F. Self-Sorting Phenomena in Complex Supramolecular Systems. Chem. Rev. 2011, 111, 5784-5814.
10. Taylor, P.N.; Anderson, H.L. Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders. J. Am. Chem. Soc. 1999, 121, 11538-11545.
11. Shivanyuk, A.; Rebek, J., Jr. Social Isomers in Encapsulation Complexes. J. Am. Chem. Soc. 2002, 124, 12074-12075.
12. Legrand, Y.M.; van der Lee, A.; Barboiu, M. Self-Optimizing Charge-Transfer Energy Phenomena in Metallosupramolecular Complexes by Dynamic Constitutional Self-Sorting. Inorg. Chem. 2007, 46, 9540-9547.
13. Ludwig, R. Water: From Clusters to the Bulk. Angew. Chem. Int. Ed. 2001, 40, 1808-1827.
14. Hunter, C.A. Quantifying Intermolecular Interactions: Guidelines for the Molecular Recognition Toolbox. Angew. Chem. Int. Ed. 2004, 43, 5310-5324.
15. Zhang, X.; Chen, Z.; Würthner, F. Morphology Control of Fluorescent Nanoaggregates by Co-Self-Assembly of Wedge-and Dumbbell-Shaped Amphiphilic Perylene Bisimides. J. Am. Chem. Soc. 2007, 129, 4886-4887.
16. Zhang, X.; Rehm, S.; Safont-Sempere, M.M.; Würthner, F. Vesicular perylene dye nanocapsules as supramolecular fluorescent pH sensor systems. Nat. Chem. 2009, 1, 623-629.
17. Kim, H.-J.; Kim, T.; Lee, M. Responsive Nanostructures from Aqueous Assembly of Rigid-Flexible Block Molecules. Acc. Chem. Res. 2011, 44, 72-82.
18. Ryu, J.-H.; Kim, H.-J.; Huang, Z.; Lee, E.; Lee, M. Self-Assembling Molecular Dumbbells: From Nanohelices to Nanocapsules Triggered by Guest Intercalation. Angew. Chem. Int. Ed. 2006, 45, 5304-5307.
19. Lee, E.; Kim, J.-K.; Lee, M. Tubular Stacking of Water-Soluble Toroids Triggered by Guest Encapsulation. J. Am. Chem. Soc. 2009, 131, 18242-18243.
20. Li, M.; Ishihara, S.; Ji, Q.; Akada, M.; Hill, J.P.; Ariga, K. Paradigm shift from self-assembly to commanded assembly of functional materials: recent examples in porphyrin/fullerene supramolecular systems. Sci. Technol. Adv. Mater. 2012, 13, 053001:1-053001:14.
21. García, F.; Sánchez, L. Dendronized Triangular Oligo(phenylene ethynylene) Amphiphiles: Nanofibrillar Self-Assembly and Dye Encapsulation. Chem. Eur. J. 2010, 16, 3138-3146.
22. García, F.; Sánchez, L. Structural Rules for the Chiral Supramolecular Organization of OPE-based Discotics: Induction of Helicity and Amplification of Chirality. J. Am. Chem. Soc. 2012, 134, 734-742.
23. García, F.; Aparicio, F.; Fernández, G.; Sánchez, L. Solvophobic Effects in the Self-Assembly of Triangular-Shape Amphiphilic Oligo(phenyleneethynylenes). Org. Lett. 2009, 11, 2748-2751.
24. Yoosaf, K.; Belbakra, A.; Armaroli, N.; Llanes-Pallas, A.; Bonifazi, D. Engineering spherical nanostructures through hydrogen bonds. Chem. Commun. 2009, 2830-2832.
25. Mahesh, S.; Thirumalai, R.; Yagai, S.; Kitamura, A.; Ajayaghosh, A. Role of complementary H-bonding interaction of a cyanurate in the self-assembly and gelation of melamine linked tri(p-phenyleneethynylene)s. Chem. Commun. 2009, 5984-5986.
26. Yagai, S.; Mahesh, S.; Kikkawa, Y.; Unoike, K.; Karatsu, T.; Kitamura, A.; Ajayaghosh, A. Toroidal Nanoobjects from Rosette Assemblies of Melamine-Linked Oligo(p-phenyleneethynylene)s and Cyanurates. Angew. Chem. Int. Ed. 2008, 47, 4691-4694.
27. Ajayaghosh, A.; Varghese, R.; Praveen, V.K. From Vesicles to Helical Nanotubes: A Sergeant-and-Soldiers Effect in the Self-Asssembly of Oligo(p-phenyleneethynylene)s. Angew. Chem. Int. Ed. 2006, 45, 7729-7732.
28. Seo, S.H.; Chang, J.Y.; Tew, G.N. Self-Assembled Vesicles from an Amphiphilic ortho-Phenylene Ethynylene Macrocycle. Angew. Chem. Int. Ed. 2006, 45, 7526-7530.
29. Ajayaghosh, A.; Varghese, R.; Praveen, V.K.; Mahesh, S. Evolution of Nano-to Microsized Spherical Assemblies of a Short Oligo(p-phenyleneethynylene) into superstructured Organogels. Angew. Chem. Int. Ed. 2006, 45, 3261-3264.
30. Levitus, M.; Schmieder, K.; Ricks, H.; Shimizu, K.D.; Bunz, U.H.F.; Garcia-Garibay, M.A. Steps to Demarcate the Effects of Chromophore Aggregation and Planarization in Poly(phenyleneethynylene)s. 1. Rotationally Interrupted Conjugation in the Excited States of 1,4-Bis(phenylethynyl)benzene. J. Am. Chem. Soc. 2001, 123, 4259-4265.
31. Bunz, U.H.F. Poly(aryleneethynylene)s: Synthesis, Properties, Structures and Applications. Chem. Rev. 2000, 100, 1605-1644.
32. Van Rijn, P.; Savenije, T.J.; Stuart, M.C.A.; van Esch, J.H. Amphiphilic conjugated thiophenes for self-assembling antenna systems in water. Chem. Commun. 2009, 2163-2165.
33. Bairi, P.; Roy, B.; Nandi, A.K. A light harvesting Bi-component hydrogel with a riboflavin acceptor. Chem. Commun. 2012, 48, 10850-10852.
34. Mayoral, M.J.; Rest, C.; Schellheimer, J.; Stepanenko, V.; Fernandez, G. Narcissistic versus Social Self-Sorting of Oligophenyleneethynylene Derivatives: From Isodesmic Self-Assembly to Cooperative Co-Assembly. Chem. Eur. J. 2012, 18, 15607-15611.
35. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Polymeric Rotaxanes. Chem. Rev. 2009, 109, 5974-6023.
36. Harada, A.; Takashima, Y.; Yamaguchi, H. Cyclodextrin-based supramolecular polymers. Chem. Soc. Rev. 2009, 38, 875-882.
37. Tomimasu, N.; Kanaya, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. Social Self-Sorting: Alternating Supramolecular Oligomer Consisting of Isomers. J. Am. Chem. Soc. 2009, 131, 12339-12343.
38. Lemmers, M.; Sprakel, J.; Voets, I.K.; van der Gucht, J.; Stuart, M.A.C. Multiresponsive Reversible Gels Based on Charge-Driven Assembly. Angew. Chem. Int. Ed. 2010, 49, 708-711.
39. Hartgerink, J.D.; Beniash, E.; Stupp, S.I. Self-Assembly and mineralization of peptide-amphiphile nanofibers. Science 2001, 294, 1684-1688.
40. Hartgerink, J.D.; Beniash, E.; Stupp, S.I. Peptide-amphiphile nanofibers: A versatile scaffold for the preparation of Self-assembling materials. Proc. Natl. Acad. Sci. USA 2002, 99, 5133-5138.
41. Behanna, H.A.; Donners, J.J.J.M.; Gordon, A.C.; Stupp, S.I. Coassembly of Amphiphiles with Opposite Peptide Polarities into Nanofibers. J. Am. Chem. Soc. 2005, 127, 1193-1200.
42. Swanekamp, R.J.; DiMaio, J.T.M.; Bowerman, C.J.; Nilsson, B.L. Coassembly of Enantiomeric Amphipathic Peptides into Amyloid-Inspired Rippled β-Sheet Fibrils. J. Am. Chem. Soc. 2012, 134, 5556-5559.
43. Pal, A.; Besenius, P.; Sijbesma, R.P. Self-Sorting in Rod-like Micelles of Chiral Bisurea Bolaamphiphiles. J. Am. Chem. Soc. 2011, 133, 12987-12989.
44. Pal, A.; Karthikeyan, S.; Sijbesma, R.P. Coexisting Hydrophobic Compartments through Self-Sorting in Rod-like Micelles of Bisurea Bolaamphiphiles. J. Am. Chem. Soc. 2010, 132, 7842-7843.
45. Ulijn, R.V. Enzyme-responsive materials: A new class of smart biomaterials J. Mater. Chem. 2006, 16, 2217-2225.
46. Jiang, L.; Yan, Y.; Drechsler, M.; Huang, J. Enzyme-triggered model self-assembly in surfactant-cyclodextrin systems. Chem. Commun. 2012, 48, 7347-7349.
47. 2 system. ACS Nano 2011, 5, 6736-6742.