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Effects of different light irradiations on structure and optical properties of methoxy-substituted tetraphenylporphyrins

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Abstract

UV lamp, filtered halogen lamp (at 425 nm) and Green laser (532 nm) experiments on a series of meso-substituted tetra phenyl porphyrin, TPP, bearing methoxy peripheral groups together with a metal derivate of 3,4 dimethoxy TPP were lead to different protonation and aggregation structures. Properties of irradiated porphyrins were investigated using their absorption and emission spectra in dichloromethane solution. The results show that the optical properties of the TPP derivates depend on light irradiation source, which shows the tuning of the absorption and emission spectra of the TPP derivates. From the dynamic light scattering measurements, the size distribution of samples was estimated about 5–15 nm in solvent after irradiation. Atomic force microscopy images of deposited porphyrins on the glass surface were shown average particle size between 10 and 30 nm. Particularly, self-assembly of the porphyrin derivates was also observed when green laser was used. We suggest that the irradiation source plays an important role in the controlling of size and morphology of products, and we propose a self-organization model to explain the formation of the porphyrin nanostructures.

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References

  1. K.S. Suslik, N.A. Rakov, M.E. Kosak, J.H. Chou, The materials chemistry of porphyrins and metallo-porphyrins. J. Porphyr. Phthalocyanines 4, 407–413 (2000)

    Article  Google Scholar 

  2. J. T. Hupp, S. T. Nguyen, Functional nanostructured molecular materials. Interface Fall 28–32 (2001)

  3. Y. Zhu, L. Qian, M. Xue, Q. Sheng, Q. Zhang, Y. Liu, Morphological control of copper phthalocyanine films by protonation-electrophoretic deposition. Appl. Surf. Sci. 257, 2625–2632 (2011)

    Article  CAS  Google Scholar 

  4. V. Snitka, M. Rackaitis, R. Rodaite, Assemblies of TPPS4 porphyrin investigated by TEM, SPM and UV–Vis spectroscopy. Sens. Actuators B. 109, 159–166 (2005)

    Article  CAS  Google Scholar 

  5. R.F. Service, Strength in numbers. Science 295, 2395–2407 (2002)

    Article  CAS  Google Scholar 

  6. N.A. Savastenko, V. Brüser, Plasma modification of self-assembled structures of CoTMPP molecules, Appl. Surf. Sci. 257, 3480–3488 (2011)

    Google Scholar 

  7. G.M. Whitesides, J.P. Mathias, C.T. Seto, Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures. Science 254, 1312–1319 (1991)

    Article  CAS  Google Scholar 

  8. N.B. Bowden, M. Weck, I.S. Choi, G.M. Whitesides, Molecule-mimetic chemistry and mesoscale self-assembly. Acc. Chem. Res. 34, 231–238 (2001)

    Article  CAS  Google Scholar 

  9. R. Rotomskis, R. Augulis, V. Snitka, R. Valiokas, B. Liedberg, Hierarchical structure of TPPS4 J-aggregates on substrate revealed by atomic force microscopy. J. Phys. Chem. B. 108, 2833–2838 (2004)

    Article  CAS  Google Scholar 

  10. J.H. Fuhrhop, U. Bindig, U. Siggel, Rods and vesicular tubules made of 14,16-diaminoporphyrins. J. Am. Chem. Soc. 115, 11036–11037 (1993)

    Article  CAS  Google Scholar 

  11. J. Li, A. Ambroise, S.I. Yang, J.R. Diers, J. Seth, C.R. Wack, D.F. Bocian, D. Holten, J.S. Lindsey, Template-directed synthesis, excited-state photodynamics, and electronic communication in a hexameric wheel of porphyrins. J. Am. Chem. Soc. 121, 8927–8940 (1999)

    Article  CAS  Google Scholar 

  12. K. Kadish, K. Smith, R. Guilard (eds.), In the Porphyrin Handbook. (Academic Press, New York, 2000) 6, 1–3

  13. S. H. Chen, J. S. Huang, P. Tartaglia (eds.) Structure and Dynamics of Strongly Interacting Colloids and Supramolecular Aggregates in Solution (Luwer, Dordrecht, 1992)

  14. F. Mallamace (ed.) Scaling Concepts and Complex Fluids. (Compositori, Bologna, 1995)

  15. J.M. Lehn, Supramolecular Chemistry (VCH, Weinheim, 1995)

    Book  Google Scholar 

  16. A. Sane, M.C. Thies, The formation of fluorinated tetraphenylporphyrin nanoparticles via rapid expansion processes: RESS vs RESOLV. J. Phys. Chem. B. 109, 19688–19695 (2005)

    Article  CAS  Google Scholar 

  17. F.C. Spano, S. Mukamel, Nonlinear susceptibilities of molecular aggregates: enhancement of χ(3) by size. Phys. Rev. A 40, 5783–5801 (1989)

    Article  CAS  Google Scholar 

  18. M.O. Senge, M.E. Fazekas, G.A. Notaras, W.J. Blau, M. Zawadzka, Nonlinear optical properties of porphyrins. Adv. Mater. 19, 2737–2774 (2007)

    Article  CAS  Google Scholar 

  19. S.S. Belanger, J.T. Hupp, Self-assembly, symmetry, and molecular architecture: coordination as the motif in the rational design of supramolecular metallacyclic polygons and polyhedra. Acc. Chem. Res. 30, 502–518 (1997)

    Article  Google Scholar 

  20. L.A. Lucia, T. Yui, R. Sasai, S. Takagi, K. Takagi, H. Yoshida, D.G. Whitten, H. Inoue, Enhanced aggregation behavior of antimony(v) porphyrins in polyfluorinated surfactant/clay hybrid microenvironment. J. Phys. Chem. B. 107, 3789–3797 (2003)

    Article  CAS  Google Scholar 

  21. T.J. Marks, Electrically conductive metallomacrocyclic assemblies. Science 227, 881–889 (1985)

    Article  CAS  Google Scholar 

  22. K. Araki, M.J. Wagner, M.S. Wrighton, Layer-by-layer growth of electrostatically assembled multilayer porphyrin films. Langmuir 12, 5393–5398 (1996)

    Article  CAS  Google Scholar 

  23. P.G. Van Patten, A.P. Shreve, R.J. Donohoe, Structural and photophysical properties of a water-soluble porphyrin associated with polycations in solution and electrostatically-assembled ultrathin films. J. Phys. Chem. B. 104, 5986–5992 (2000)

    Article  Google Scholar 

  24. D. M Guldi, F. Pellarini, M. Prato, C. Granito, L. Troisi, Layer-by-layer construction of nanostructured porphyrin-fullerene electrodes. Nano. Lett. 2, 965–968 (2002)

    Google Scholar 

  25. D.M. Kaschak, J.T. Lean, C.C. Waraksa, G.B. Saupe, H. Usami, T.E. Mallouk, Photoinduced energy and electron transfer reactions in lamellar polyanion/polycation thin films: toward an inorganic “leaf”. J. Am. Chem. Soc. 121, 3435–3445 (1999)

    Article  CAS  Google Scholar 

  26. R. Paolesse, D. Monti, L. La Monica, M. Venanzi, A. Froiio, S. Nardis, C. Di Natale, E. Martinelli, A.D. Amico, Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors. Chem. Eur. J. 8, 2476–2483 (2002)

    Article  CAS  Google Scholar 

  27. M.C. Cottin, J. Schaffert, A. Sonntag, H. Karacuban, R. Möller, C.A. Bobisch, Supramolecular architecture of organic molecules: PTCDA and CuPc on a Cu(1 1 1) substrate. Appl. Surf. Sci. 258(6), 2196–2200 (2012)

    Article  CAS  Google Scholar 

  28. Z.J. Zhang, S.F. Hou, Z.H. Zhu, Z.F. Liu, Preparation and characterization of a porphyrin self-assembled monolayer with a controlled orientation on gold. Langmuir 16, 537–540 (2000)

    Article  CAS  Google Scholar 

  29. Z.J. Zhang, R.S. Hu, Z.F. Liu, Formation of a porphyrin monolayer film by axial ligation of protoporphyrin IX zinc to an amino-terminated silanized glass surface. Langmuir 16, 1158–1162 (2000)

    Article  CAS  Google Scholar 

  30. D.T. Gryko, C. Clausen, J.S. Lindsey, Thiol-derivatized porphyrins for attachment to electroactive surfaces. J. Org. Chem. 64, 8635–8647 (1999)

    Article  CAS  Google Scholar 

  31. D.L. Pilloud, F. Rabanal, B.R. Gibney, R.S. Farid, P.L. Dutton, C.C. Moser, Self-assembled monolayers of synthetic hemoproteins on silanized quartz. J. Phys. Chem. B. 102, 1926–1937 (1998)

    Article  CAS  Google Scholar 

  32. A. Ulman, An Introduction of Ultrathin Organic Films, from Langmuir–Blodgett Films to Self-Assembly (Academic Press, San Diego, 1991)

    Google Scholar 

  33. J.M. Kroon, E.J.R. Sudholter, A. Schenning, R.J.M. Nolte, Self-organization of amphiphilic porphyrins at the air-water interface. Langmuir 11, 214–220 (1995)

    Article  CAS  Google Scholar 

  34. L. Zhang, Q. Lu, M.H. Liu, Fabrication of chiral Langmuir–Schaefer films from achiral TPPS and amphiphiles through the adsorption at the air/water interface. J. Phys. Chem. B. 107, 2565–2569 (2003)

    Article  CAS  Google Scholar 

  35. L. Zhang, J. Yuan, M.H. Liu, Supramolecular chirality of achiral TPPS complexed with chiral molecular films. J. Phys. Chem. B. 107, 12768–12773 (2003)

    Article  CAS  Google Scholar 

  36. J. A. Schwarz, C. I. Contescu, K. Putyera (eds.), In Dekker Encyclopedia of Nanoscience and Nanotechnology. (Taylor & Francis Group, New York, 2004), pp. 3481–3487

  37. T. Milic, J.C. Garno, J.D. Batteas, G. Smeureanu, C.M. Drain, Self-organization of self-assembled tetrameric porphyrin arrays on surfaces. Langmuir 20, 3974–3983 (2004)

    Article  CAS  Google Scholar 

  38. G.D. Luca, G. Pollicino, A. Romeo, L.M. Scolaro, Sensing behavior of tetrakis(4-sulfonatophenyl)porphyrin thin films. Chem. Mater. 18, 2005–2007 (2006)

    Article  Google Scholar 

  39. G.D. Luca, G. Pollicino, A. Romeo, S. Patane, L.M. Scolaro, Control over the optical and morphological properties of UV-deposited porphyrin structures. Chem. Mater. 18, 5429–5436 (2006)

    Article  Google Scholar 

  40. D.L. Akins, H.R. Zhu, C. Guo, Aggregation of tetraaryl-substituted porphyrins in homogeneous solution. J. Phys. Chem. 100, 5420–5425 (1996)

    Article  CAS  Google Scholar 

  41. R.F. Khairutdinov, N. Serpone, Photoluminescence and transient spectroscopy of free base porphyrin aggregates. J. Phys. Chem. B. 103, 761–769 (1999)

    Article  CAS  Google Scholar 

  42. A.D. Adler, F.K. Longo, J.A. Finarelli, Simplified synthesis for meso-tetraphenylporphine. J. Org. Chem. 32, 476–477 (1976)

    Article  Google Scholar 

  43. A.D. Adler, F.R. Longo, W. Shergalis, Mechanistic Investigations of porphyrin syntheses. i. preliminary studies on ms-tetraphenylporphin. J. Am. Chem. Soc. 863, 145–3149 (1964)

    Google Scholar 

  44. G.S.S. Saini, O.K. Medhi, A.L. Verma, Simultaneous formation of mono- and dications of free-base tetraphenylporphin during photo-oxidation probed by resonance Raman and absorption techniques. Chem. Phys. Lett. 322, 293–299 (2000)

    Article  CAS  Google Scholar 

  45. A. Stone, E.B. Fleischer, The molecular and crystal structure of porphyrin diacids. J. Am. Chem. Soc. 902, 735–2748 (1968)

    Google Scholar 

  46. S. Rayati, S. Zakavi, A. Ghaemi, P.J. Carroll, Core protonation of meso-tetraphenylporphyrin with tetrafluoroboric acid: unusual water-mediated hydrogen bonding of H4T PP2+ to the counterion. Tet. Lett. 4, 9664–9667 (2008)

    Google Scholar 

  47. G.D. Luca, A. Romeo, L.M. Scolaro, G. Ricciardi, A. Rosa, Evidence for tetraphenylporphyrin monoacids. Inorg. Chem. 46, 5979–5988 (2007)

    Article  Google Scholar 

  48. M.A. Castriciano, A. Romeo, V. Villari, N. Micali, L.M. Scolaro, Nanosized porphyrin J-aggregates in water/AOT/decane microemulsions. J. Phys. Chem. B. 108, 9054–9059 (2004)

    Article  CAS  Google Scholar 

  49. S.C.M. Gandini, V.E. Yushmanov, I.E. Borissevitch, M. Tabak, Interaction of the tetra(4-sulfonatophenyl)porphyrin with ionic surfactants: aggregation and location in micelles. Langmuir 15, 6233–6243 (1999)

    Article  CAS  Google Scholar 

  50. G.D. Luca, A. Romeo, L.M. Scolaro, Counteranion dependent protonation and aggregation of tetrakis(4-sulfonatophenyl)porphyrin in organic solvent. J. Phys. Chem. B. 110, 7309–7315 (2006)

    Article  Google Scholar 

  51. Z.M. Ou, H. Yao, K. Kimura, Preparation and optical properties of organic nanoparticles of porphyrin without self-aggregation. J. Photochem. Photobiol. A. Chem. 189, 7–14 (2007)

    Article  CAS  Google Scholar 

  52. E.G. McRae, M. Kasha, Enhancement of phosphorescence ability upon aggregation of dye molecules. J. Chem. Phys. 28, 721–722 (1958)

    Article  CAS  Google Scholar 

  53. E. G. McRae, M. Kasha, In physical processes in radiation biology. (Academic Press, New York, 1964) pp. 23–42

  54. J.M. Ribo, J.M. Bofill, J. Crusats, R. Rubires, Point-dipole approximation of the exciton coupling model versus. Chem. Eur. J. 7, 2733–2737 (2001)

    Article  CAS  Google Scholar 

  55. T. Kobayashi (ed.), J-aggregates. (World scientific, Singapore, 1996)

  56. T. Terui, T. Sekiguchi, Y. Wakayama, T. Kamikado, S. Mashiko, Structural study of porphyrin isomers on metal substrates by using STM. Thin Solid Films 464, 384–387 (2004)

    Article  Google Scholar 

  57. H. Song, C.A. Reed, W.R. Scheidt, Metalloporphyrin .pi.-cation radicals: intrinsically ruffled or planar core conformations? Molecular structure mesitylporphinatocopper(II) hexachloroantimonate. J. Am. Chem. Soc. 111, 6865–6868 (1989)

    Article  CAS  Google Scholar 

  58. B.S. Erler, W.F. Scholz, Y. Lee, W.R. Scheidt, C.A. Reed, Spin coupling in metalloporphyrin.pi.-cation radicals. J. Am. Chem. Soc. 109, 2644–2652 (1987)

    Article  CAS  Google Scholar 

  59. T. K. Miyamoto, N. Sugita, Y. Matsumoto, Y. Sasaki, M. Konno, A new antineoplastic methylgermanium(IV)porphyrin. Chem. Lett. 1695–1698 (1983)

  60. H. Shahroosvand, E. Mohajerani, N. Safari, S. Osati, I.A. Alidokht, Preparation and optical properties of substituted hydroxyl porphyrin nanostructure by UV light and green laser (532 nm) irradiations. Int. J. Opt. Photon. 3, 33–44 (2009)

    Google Scholar 

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Acknowledgments

The authors also wish to thank the Shahid Beheshti University for financial support.

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Authors and Affiliations

  1. Chemistry Department, University of Zanjan, Zanjan, Iran

    Hashem Shahroosvand

  2. Chemistry Department, Shahid Beheshti University, G.C, Evin, Tehran, Iran

    Nasser Safari

  3. Organic Material and Polymer Photonics Lab, Laser Research Institute, Shahid Beheshti University, Evin, Tehran, Iran

    Ezeddin Mohajerani

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  1. Hashem Shahroosvand
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  2. Nasser Safari
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Correspondence to Hashem Shahroosvand.

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Shahroosvand, H., Safari, N. & Mohajerani, E. Effects of different light irradiations on structure and optical properties of methoxy-substituted tetraphenylporphyrins. J IRAN CHEM SOC 11, 1173–1182 (2014). https://doi.org/10.1007/s13738-013-0385-3

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