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On the Formation of Nanostructures from Stilbazolium-like Dyes

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Abstract

Nanostructures with well-defined shape and highly monodisperse size were fabricated from model stilbazolium-like dyes with specific molecular structural and conformational characteristics. With the help of absorption and fluorescence optical spectroscopy, the correlated spectroscopy (COSY) and two- dimensional nuclear Overhauser effect spectroscopy (2D NOESY) techniques, along with X-ray diffraction (XRD) measurement, distinctively different aggregation processes of the model molecules are demonstrated. For model dye molecule with linear donor–π system–acceptor (D–π–A) structure, strong D–A pair, and planar conformation, specific intermolecular interaction was identified and special crystal structures as well as spectral properties were observed. For model dye molecules bearing nonlinear D–π–A–π–D structure, weak D–A pair but actual amphiphilic characteristics, a special aggregation process was confirmed and a focused size distribution of the produced nanostructures was obtained.

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References

  • M. Adams, Z. Dogic, S.L. Keller and S. Fraden, Entropically driven microphase transitions in mixtures of colloidal rods and spheres. Nature 393 (1998) 349-352

    Article  CAS  Google Scholar 

  • A. Albert, Heterocyclic Chemistry. New York: Oxford University Press (1968).

    Google Scholar 

  • I.D.L. Albert, T.J. Marks and M.A. Ratner, Large molecular hyperpolarizabilities. Quantitative analysis of aromaticity and auxiliary donor–acceptor effects. J. Am. Chem. Soc. 119 (1997) 6575-6582

    Article  CAS  Google Scholar 

  • D.B. Amabilino, P.R. Anelli, P.R. Ashton, G.R. Brown, E. Córdova, L.A. Godinez, W. Hanes, A.E. Kaifer, D. Pjilip, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, M.S. Tolley and D.J. Williams, Molecular meccano. 3. constitutional and translational isomerism in [2] catenanes and [n] pseudorotaxanes. J. Am. Chem. Soc. 117 (1995) 11142-11170

    Article  Google Scholar 

  • V.J. Anderson and H.N.W. Lekkerkerker, Insights into phase transition kinetics from colloid science. Nature 416 (2002) 810-814

    Article  Google Scholar 

  • B. Cabezon, J.G. Cao, F.M. Raymo, J.F. Stoddart, A.J.P. White and D.J. Williams, Molecular meccano, part 59 self-complementary [2] catenanes and their related [3] catenanes. Chem. Eur. J. 6 (2000) 2262-2273

    Article  CAS  Google Scholar 

  • J.A.A.W. Elemans, A.E. Rowan and R.J.M. Nolte, Hierarchical self-assembly of amphiphilic metallohosts to give discrete nanostructures. J. Am. Chem. Soc. 124 (2002) 1532-1540

    Article  CAS  Google Scholar 

  • E.S. Emerson, M.A. Colin, A.E. Rosenoff, K.S. Norland, H. Rodriguez, D. Chin and G.R. Bird, The geometrical structure and absorption spectrum of a cyanine dye aggregate. J. Phys. Chem. 71 (1967) 2396-2403

    Article  CAS  Google Scholar 

  • A.D.L. Escosura, M.V. Martinez-Diaz, P. Thordarson, A.E. Rowan, R.J.M. Nolte and T. Torres, Donor–acceptor phthalocyanine nanoaggregates. J. Am. Chem. Soc. 125 (2003) 12300-12308

    Article  Google Scholar 

  • S.R. Forrest, Ultrathin organic films grown by organic molecular beam deposition and related techniques. Chem. Rev. 97 (1997) 1793-1896

    Article  CAS  Google Scholar 

  • M.A. Fox and M. Chanon, Photoinduced Electron Transfer Part A. New York: Elsevier (1988).

    Google Scholar 

  • H.B. Fu and J.N. Yao, Size effects on the optical properties of organic nanoparticles. J. Am. Chem. Soc. 123 (2001) 1434-1439

    Article  CAS  Google Scholar 

  • H.B. Fu, B.H. Loo, D.B. Xiao, R.M. Xie, X.H. Ji, J.N. Yao, B.W. Zhang and L.Q. Zhang, Multiple emission from 1,3-diphenyl-5-pyrenyl-2-pyrazoline nanoparticles: evolution from molecular to nanoscale to bulk materials. Angew. Chem. Int. Ed. 41 (2002) 962-965

    Article  CAS  Google Scholar 

  • H.B. Fu, D.B. Xiao, J.N. Yao and G.Q. Yang, Nanofibers of 1,3-diphenyl-2-pyrazoline induced by cetyltrimethylammonium bromide micelles. Angew. Chem. Int. Ed. 42 (2003) 2883-2886

    Article  CAS  Google Scholar 

  • M.M. Habashy, F.EL. Zawawi, M.S. Antonious, A.K. Sheriff and M.S.A. Abdel-Mottaleb, Electronic structures of solvent-polarity indicators: electronic & proton magnetic resonance spectra of donor–acceptor chromogens. Ind. J. Chem. 24 (1985) 908-912

    Google Scholar 

  • U. Hofstra, R.B.M. Koehorst and T.J. Schaafsma, Excited-state properties of water-soluble porphyrin dimers. Chem. Phys. Lett. 130 (1986) 555-559

    Article  CAS  Google Scholar 

  • D. Horn and J. Rieger, Organic nanoparticles in aqueous phase – theory, experiment and use. Angew. Chem. Int. Ed. 40 (2001) 4330-4361

    Article  CAS  Google Scholar 

  • A. Ibanez, S. Maximov, A. Guiu, C. Chaillout and P.L. Baldeck, Controlled nanocrystallization of organic molecules in sol–gel glasses. Adv. Mater. 10 (1998) 1540-1543

    Article  CAS  Google Scholar 

  • H. Kasai, H.S. Nalwa, H. Oikawa, S. Okada, H. Matsuda, N. Minami, A. Kakuta, K. Ono, A. Mukoh and H. Nakanishi, A novel preparation method of organic microcrystals. Jpn. J. Appl. Phys. 31 (1992) L1132-1134

    Article  CAS  Google Scholar 

  • N. Kiriy, E. Jähne, H. Adler, M. Schneider, A. Kiriy, G. Gorodyska, S. Minko, D. Jehnichen, P. Simon, A.A. Fokin and M. Stamm, One-dimensional aggregation of␣regioregular polyalkylthiophenes. Nano Lett. 3 (2003) 707-712

    Article  CAS  Google Scholar 

  • S. Link, M.B. Mohamed and M.A. EI-Sayed, Simulation of the optical absorption spectra of gold nanorods as a function of their aspect ratio and the effect of the medium dielectric constant. J. Phys. Chem. B 103 (1999) 3073-3077

    Article  CAS  Google Scholar 

  • P. Modrich, DNA mismatch correction. Annu. Rev. Biochem. 56 (1987) 435-466

    Article  CAS  Google Scholar 

  • H. Nakanishi and H. Katagi, Microcrystals of polydiacetylene derivatives and their linear and nonlinear optical properties. Supramol. Sci. 5 (1998) 289-295

    Article  CAS  Google Scholar 

  • Handbook of Advanced Electronic and Photonic Materials and Devices. Vol 6, Nanostructured Materials. San Diego, CA: Academic Press (2001).

    Google Scholar 

  • Oikawa H., H. Kasai & H. Nakanishi, 2002. In anisotropic organic materials; ACS Symposium Ser. 798, Glaser, R., Kasizynski, P. eds. American Chemical Society, Washington, DC, Chapter 11, pp. 158–168, and references therein.

  • C. Pacholski, A. Kornowski and H. Weller, Self-assembly of ZnO: from nanodots to nanorods. Angew. Chem. Int. Ed. 41 (2002) 1188-1191

    Article  CAS  Google Scholar 

  • X.G. Peng, L. Manna, W.D. Yang, J. Wickham, E. Scher, A. Kadavanich and A.P. Alivisatos, Shape control of CdSe nanocrystals. Nature 404 (2000) 59-61

    Article  CAS  Google Scholar 

  • X.G. Peng, J. Wickham and A.P. Alivisatos, Kinetics of II–VI and III–V colloidal semiconductor nanocrystal growth: ‘focusing’ of size distributions. J. Am. Chem. Soc. 120 (1998) 5343-5344

    Article  CAS  Google Scholar 

  • R.L. Penn and J.F. Banfield, Imperfect oriented attachment: dislocation generation in defect-Free nanocrystals. Science 281 (1998) 969-971

    Article  CAS  Google Scholar 

  • S.G. Schulman, Fluorescence and Phosphorescence Spectroscopy: Physicochemical Principles and Practice. Oxford: New York (1977).

    Google Scholar 

  • G.V.M. Sharma, K.R. Reddy, P.R. Krishna, A.R. Sankar, P. Jayaprakash, B. Jagannadh and A.C. Kunwar, Left-handed helical twists in ‘mixed β-peptides’ derived from alternating C-linked carbo-β3-amino acids and β-hGly units. Angew. Chem. Int. Ed. 43 (2004) 3961-3965

    Article  CAS  Google Scholar 

  • Y.Z. Shen, D. Iakubczyk, F.M. Xu, J. Swiatkiewicz, P.N. Prasad and B.A. Reinhardt, Two-photon fluorescence imaging and spectroscopy of nanostructured organic materials using a photon scanning tunneling microscope. Appl. Phys. Lett. 76 (2000) 1-3

    Article  CAS  Google Scholar 

  • Z.Y. Tang, N.A. Kotov and M. Giersig, Spontaneous organization of single CdTe nanoparticles into luminescent nanowires. Science 297 (2002) 237-240

    Article  CAS  Google Scholar 

  • Z.Y. Tian, Y. Chen, W.S. Yang, J.N. Yao, L.Y. Zhu and Z.G. Shuai, Low-dimensional aggregates from stilbazolium-like dyes. Angew. Chem. Int. Ed. 43 (2004) 4060-4063

    Article  CAS  Google Scholar 

  • D.B. Xiao, L. Xi, W.S. Yang, H.B. Fu, Z.G. Shuai, Y. Fang and J.N. Yao, Size-tunable emission from 1,3-diphenyl-5-(2-anthryl)-2-pyrazoline nanoparticles. J. Am. Chem. Soc. 125 (2003) 6740-6745

    Article  CAS  Google Scholar 

  • Y.Y. Yu, S.S. Chang, C.L. Lee and C.R.C. Wang, Gold nanorods: electrochemical synthesis and optical properties. J. Phys. Chem. B 101 (1997) 6661-6664

    Article  CAS  Google Scholar 

  • C.L. Zhan and D.Y. Wang, Nonlinear dependence of␣solvent polarity effects on twisted intramolecular charge-transfer states and linear relation for electronic spectra in a stilbazolium-like dye. J. Photochem. Photobiology A: Chem. 147 (2002) 93-101

    Article  CAS  Google Scholar 

  • L.Y. Zhao, W.S. Yang, Y. Ma, J.N. Yao, Y.L. Li and H.B. Liu, Perylene nanotubes fabricated by the template method. Chem. Commun. 19 (2003) 2442-2443

    Article  Google Scholar 

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Tian, Z., Zhang, Y., Zhang, Y. et al. On the Formation of Nanostructures from Stilbazolium-like Dyes. J Nanopart Res 8, 65–77 (2006). https://doi.org/10.1007/s11051-005-6769-2

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