Lipophilic Optical Supramolecular Nano Devices in the Aqueous Phase

DOI: 10.4236/gsc.2011.11001   PDF   HTML     5,049 Downloads   11,025 Views   Citations


Nano micelles of sodium dodecyl sulphate in water were prepared as local lipophilic media for the organisation of interacting chromophores. Such arrangements were controlled by peripheric substituents to operate either as isolated chromophores or as skew oriented pairs where H-type transitions cause hysochromic absorption and J-type transitions bathochromic fluorescence. As a consequence, large Stokes' shift could be obtained.

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H. Langhals and T. Pust, "Lipophilic Optical Supramolecular Nano Devices in the Aqueous Phase," Green and Sustainable Chemistry, Vol. 1 No. 1, 2011, pp. 1-6. doi: 10.4236/gsc.2011.11001.

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The authors declare no conflicts of interest.


[1] C. J. Brabec, N. S. Sariciftci and J. C. Hummelen, Advanced Functional Materials, Vol. 11, 2001, pp. 15-26. S. Günes, H. Neugebauer and N. S. Sariciftci, “Conjugated Polymer-Based Organic Solar Cells,” Chemical Reviews, Vol. 107, 2007, pp. 1324-1338.
[2] M. Gr?tzel, “Photoelectrochemical Cells,” Nature, Vol. 414, 2001, pp. 338-344. H. Choi, S. Kim, S. O. Kang, J. Ko. M, S. Kang, J. N. Clifford, A. Forneli, E. Palomares, M. K. Nazeeruddin and M. Gr?tzel, “Stepwise Cosensitization of Nanocrystalline TiO2 Films Utilizing Al2O3 Layers in Dye-Sensitized Solar Cells,” Angewandte Chemie, Vol. 120, 2008, pp. 8383-8387; Angewandte Chemie International Edition, Vol. 47, 2008, pp. 8259-8263. F. Gao, Y. Wang, D. Shi, J. Zhang, M. Wang, X. Jing, R. Humphry-Baker, P. Wan
[3] D. Gust, T. A. Moore and A. L. Moore, “Mimicking Photosynthetic Solar Energy Transduction,” Accounts of Chemical Research, Vol. 34, 2001, pp. 40-48. M. R. Wasielewski, “Energy, Charge, and Spin Transport in Molecules and Self-Assembled Nanostructures Inspired by Photosynthesis,” Journal of Organic Chemistry, Vol. 71, 2006, pp. 5051-5066. I. Leray, B. Valeur, D. Paul, E. Regnier, M. Koepf, J. A. Wytko, C. Boudon and J. Weiss, “Photodynamics of Excitation Energy Transfer in Self-Assembled Dyads. Evidence for
[4] L. J. Huo, S. Q. Zhang, H. Y. Chen and Y. Yang, “A Polybenzo[1,2-b:4,5-b′]dithiophene Derivative with Deep HOMO Level and Its Application in High-Performance Polymer Solar Cells,” Angewandte Chemie, Vol. 122, 2010, pp. 1542-1545; Angewandte Chemie International Edition, Vol. 49, 2010, pp. 1500-1503. H. Goesmann and C. Feldmann, “Nanoparticulate Functional Materials,” Angewandte Chemie, Vol. 122, 2010, pp. 1402-1437; Angewandte Chemie International Edition, Vol. 49, 2010, pp. 1362-1395.
[5] H. Langhals, “Brightly Shining Nano Particles: Lipophilic Perylene Bisimides in Aqueous Phase,” New Journal of Chemistry, Vol. 32, 2008, pp. 21-23.
[6] G. Sonnek and F. Wolf, “Alkyl Naphthalenesulfonic Acids (Nekal BX),” Tenside, Vol. 4, 1967, pp. 325-330; Chemical Abstracts, Vol. 67, 1967, p. 118445. V. Jacopian, “Decrease of the Resin Content of Dissolving Pulps by Means of Surfactants,” Zellstoff und Papier (Leipzig), Vol. 14, 1965, pp. 310-311; Chemical Abstracts, Vol. 64, 1966, p. 36839. J. Figaret, “(Practical Test Methods for) the Effect of Surface-active Agents on the Wettability of Pigments,” Farbe + Lack, Vol. 55, 1949, pp. 234-238; Chemical Abst
[7] H. Langhals and T. Pust, “Fluorescent Nano pH Indicators Based on Supramolecular Interactions,” Zeitschrift für Naturforschung, Vol. 65b, 2010, pp. 291-294.
[8] M. Almgren and S. Swarup, In: K. L. Mittal and B. Lindman, Eds., Surfactants Solution, New York, Vol. 1, 1982, pp. 613-625; Chemical Abstracts, Vol. 101, 1984, p. 28739. A. Patist, S. G. Oh, R. Leung and D. O. Shah, “Kinetics of Micellization: Its Significance to Technological Processes,” Colloids and Surfaces A: Physicochemical and Engineering Aspects, Vol. 176, 2001, pp. 3-16; Chemical Abstracts, Vol. 134, 2000, p. 152923.
[9] For reviews see: H. Langhals, “Control of the Interactions in Multichromophores: Novel Concepts. Perylene Bisimides as Components for Larger Functional Units,” Helvetica Chimica Acta, Vol. 88, 2005, pp. 1309-1343. H. Langhals, “Cyclic Carboxylic Imide Structures as Structure Elements of High Stability. Novel Developments in Perylene Dye Chemistry,” Heterocycles, Vol. 40, 1995, pp. 477-500. H. Langhals, “Molecular Devices. Chiral, Bichromophoric Silicones: Ordering Principles in Complex Molecules,” In: F. Ga
[10] “Dynamics of Surfactant Self-Assemblies: Micelles, Microemulsions, Vesicles, and Lyotropic Phases,” In: R. Zana, Ed., Surfactant Science Series, CRC Press LLC, Florida, 2005, p. 125; Chemical Abstracts, Vol. 143, 2005, p. 200524. A. Rusanov, Micellization in Surfactant Solutions, Harwood, Amsterdam, 1998; Chemical Abstracts, Vol. 134, 2001, p. 257304. F. L. Boschke, “Topics in Current Chemistry,” Micelles, Vol. 87, Springer-Verlag, Berlin, 1980; Chemical Abstracts, Vol. 92, 1980, p. 100018. D. A. Jaeger, “S
[11] S. Demmig and H. Langhals, “Highly soluble, Lightfast Perylene Fluorescent Dyes,” Chemische Berichte, Vol. 121, 1988, pp. 225-230. H. Langhals, S. Demmig and T. Potrawa, “The Relation between Packing Effects and Solid State Fluorescence of Dyes,” Journal für Praktische Chemie, Vol. 333, 1991, pp. 733-748.
[12] H. Langhals, Dyes for Fluorescent Immunoassays, in B. Hock, Immunochemical Detection of Pesticides and their Metabolites in the Water Cycle, VCH Verlagsgesellschaft, Weinheim, 1995 (ISBN 3-527- 27137-6); Chemical Abstracts, Vol. 124, 1996, p. 24966z.
[13] H. Langhals, “Description of Properties of Binary Solvent Mixtures,” In: R. I. Zalewski, T. M. Krygowski and J. Shorter, Eds., Similarity Models in Organic Chemistry, Biochemistry and Related Fields. Studies in Organic Chemistry, Elsevier Publishers, Amsterdam, 1991, pp. 283-342 (ISBN 0-444-88161-1).
[14] W. E. Ford, “Photochemistry of 3,4,9,10-Perylene- tetracarboxylic Dianhydride Dyes: Visible Absorption and Fluorescence Spectra and Fluorescence Quantum Yields of the Mono(n-octyl)-imide Derivative in Aqueous and Non-aqueous Solutions,” Journal of Photochemistry, Vol. 34, 1986, pp. 43-54. W. E. Ford, “Photochemistry of 3,4,9,10-Perylenetetracarboxylic Dianhydride Dyes: Visible Absorption and Fluorescence of the Di(glycyl)imide Derivative Monomer and Dimer in Basic Aqueous Solutions,” Journal of Photochemist
[15] J. Seibt, P. Marquetand, V. Engel, Z. Chen, V. Dehm and F. Würthner, “On the Geometry Dependence of Molecular Dimer Spectra with an Application to Aggregates of Perylene Bisimide,” Chemical Physics, Vol. 328, 2006, pp. 354-362. J. M. Giaimo, J. V. Lockard, L. E. Sinks, A. M. Scott, T. M. Wilson and M. R. Wasielewski, “Excited Singlet States of Covalently Bound, Cofacial Dimers and Trimers of Perylene- 3,4:9,10-bis(dicarboximide)s,” Journal of Physical Chemistry A, Vol. 112, 2008, pp. 2322-2330. R. O. Marcon
[16] A. S. Davydov, “Theory of Absorption Spectra of Molecular Crystals,” Zhur. Eksptl. i Teoret. Fiz., Vol. 18, 1948, pp. 210-218; Chemical Abstracts, Vol. 43, 1949, p. 4575f. A. S. Davydow, Theory of Molecular Excitations, McGraw-Hill, New York, 1962. M. Kasha, H. R. Rawls and M. A. El-Bayoumi, “The Exciton Model in Molecular Spectroscopy,” Pure and Applied Chemistry, Vol. 11, 1965, pp. 371-392.
[17] G. Scheibe, “Variability of the Absorption Spectra of some Sensitizing Dyes and its Cause,” Angewandte Chemie, Vol. 49, 1936, p. 563.
[18] T. F?rster, “Migration of Energy and Fluorescence,” Naturwissenschaften, Vol. 33, 1946, p. 166-175; Chemical Abstracts, Vol. 41, 1947, p. 36668. T. F?rster, “Electron Spectra of Coupled Molecules,” Pure and Applied Chemistry, Vol. 4, 1962, pp. 121-134.
[19] E. Jelley, “Spectral Absorption and Fluorescence of Dyes in the Molecular State,” Nature, Vol. 138, 1936, p. 1009.
[20] S. M. Bachrach, Computational Organic Chemistry, John Wiley & Sons, New York, 2007, pp. 394-395 (ISBN 978-0-471-71342-5). R. Villar, M. J. Gil, J. I. Garcia and V. Martinez-Merino, “Are AM1 Ligand-protein Binding Enthalpies Good Enough for Use in the Rational Design of New Drugs?,” Journal of Computational Chemistry, Vol. 26, 2005, pp. 1347-1358; Chemical Abstracts, Vol. 143, 2005, p. 410902. (We thank Prof. R. de Vivie-Riedle and Dr. H. U. Wagner for helpful discussions.)
[21] T. F?rster, “Migration of Energy and Fluorescence,” Naturwissenschaften, Vol. 33, 1946, pp. 166-175; Chemical Abstracts, Vol. 41, 1947, p. 36668. T. F?rster, “Intermolecular energy transference and fluorescence,” Annals of Physics, Vol. 6, 1948, Folge, No. 2, pp. 55-75; Chemical Abstracts, Vol. 43, 1949, p. 31172. T. F?rster, “Investigations of the Intermolecular Transfer of the Energy of Electronic Exitation,” Zeitschrift für Elektrochemie, Vol. 53, 1949, pp. 93-99; Chemical Abstracts, Vol. 43, 1949, p. 33
[22] H. Langhals and R. Ismael, “Cyclophanes as Model Compounds for Permanent, Dynamic Aggregates: Induced Chirality with Strong CD Effects,” European Journal of Organic Chemistry, Vol. 1998, No. 9, 1998, pp. 1915-1917.
[23] H. Langhals, “Dyes for Fluorescent Solar Collectors,” Nachrichten aus Chemie, Technik und Laboratorium, Vol. 28, 1980, pp. 716-718; Chemical Abstracts, Vol. 95, 1981, p. R9816q.

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