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Introduction

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Azo Polymers

Part of the book series: Soft and Biological Matter ((SOBIMA))

Abstract

This chapter is the introduction of this book to discuss the background and terminology related to azo compounds and azo polymers. As azo groups play a critically important role in determining the functions of azo polymers, their structures and spectroscopic features are discussed first. Light absorption and electronic excitation of the aromatic azo cores are then discussed to understand the initial steps to cause the photoresponsive variations of azo polymers. Photoisomerization of azo groups, which is the most important concept for understanding the contents of this book, is briefly introduced here. Based on the understanding, azo functional structures are classified according to their spectral features and isomerization behavior. Finally, a brief retrospect of azo polymers is given to end this chapter.

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References

  1. Nuyken, O.: Azo polymers. In: Kroschwitz, J.I. (ed.) Encyclopedia of Polymer Science and Engineering, vol. 2, pp. 158–175. Wiley, New York (1985)

    Google Scholar 

  2. Kumar, G.S.: Azo Functional Polymers: Functional Group Approach in Macromolecular Design. Technomic Publishing Co. Inc., Lancaster (1992)

    Google Scholar 

  3. Zollinger, H.: Azo and Diazo Chemistry: Aliphatic and Aromatic Compounds. Interscience Publishers Inc., New York (1961)

    Google Scholar 

  4. Zollinger, H.: Color Chemistry: Syntheses, Properties and Applications of Organic Dyes and Pigments, 2nd edn. VCH publishers Inc., New York (1991)

    Google Scholar 

  5. Hunger, K., Mischke, P., Rieper, W., Raue, R.: Azo dyes. In: Gerhartz, W. (ed.) Ullmann’s Encyclopedia of Industrial Chemistry, vol. A3, 5th edn, pp. 245–324. VCH, Weihheim (1985)

    Google Scholar 

  6. Burawoy, A.: Studies in the light absorption of organic compounds. Part VIII. azo-compounds. J. Chem. Soc. 1865–1869 (1937)

    Google Scholar 

  7. Hartley, G.S.: The cis-form of azobenzene. Nature 140, 281–281 (1937)

    Article  CAS  Google Scholar 

  8. Hartley, G.S.: The cis-form of azobenzene and the velocity of the thermal cis → trans conversion of azobenzene and some derivatives. J. Chem. Soc. 633–642 (1938)

    Google Scholar 

  9. Harada, J., Ogawa, K., Tomoda, S.: Molecular motion and conformational interconversion of azobenzenes in crystals as studied by X-ray diffraction. Acta. Cryst. B 53, 662–672 (1997)

    Article  Google Scholar 

  10. Tsuji, T., Takashima, H., Takeuchi, H., Egawa, T., Konaka, S.: Molecular structure and torsional potential of trans-azobenzene. A gas electron diffraction study. J. Phys. Chem. A 105, 9347–9353 (2001)

    Article  CAS  Google Scholar 

  11. Levine, I.N.: Quantum Chemistry, 3rd edn. Allyn and Bacon Inc., Boston (1983)

    Google Scholar 

  12. Hameka, H.F.: Advanced Quantum Chemistry: Theory of Interactions Between Molecules and Electromagnetic Fields. Addison-Wesley Publishing Company, Massachusetts (1965)

    Google Scholar 

  13. Wang, X.G., Kumar, J., Tripathy, S.K., Li, L., Chen, J.I., Marturunkakul, S.: Epoxy-based nonlinear optical polymers from post azo coupling reaction. Macromolecules 30, 219–225 (1997)

    Article  CAS  Google Scholar 

  14. Rau, H.: Photoisomerization of azobenzenes. In: Rabek, J.F. (ed.) Photochemistry and Photophysics, vol. 2, pp. 119–141. CRC Press, Boca Raton (1990)

    Google Scholar 

  15. Rau, H.: Azo compounds. In: Dürr, H., Bouas-Laurent, H. (eds.) Photochromism: Molecules and Systems, pp. 165–192. Elsevier, Amsterdam (1990)

    Google Scholar 

  16. Barltrop, J.A., Coyle, J.D.: Principles of Photochemistry. John Wiley & Sons Ltd, New York (1978)

    Google Scholar 

  17. Turro, N.J.: Modern Molecular Photochemistry. The Benjamin/Cummings Publishing Co. Inc., California (1978)

    Google Scholar 

  18. Beveridge, D.L., Jaffé, H.H.: The electronic structure and spectra of cis- and trans-azobenzene. J. Am. Chem. Soc. 88, 1948–1953 (1966)

    Article  CAS  Google Scholar 

  19. Åstrand, P.O., Ramanujam, P.S., Hvilsted, S., Bak, K.L., Sauer, S.P.A.: Ab initio calculation of the electronic spectrum of azobenzene dyes and its impact on the design of optical data storage materials. J. Am. Chem. Soc. 122, 3483–3487 (2000)

    Article  Google Scholar 

  20. Fliegl, H., Köhn, A., Hättig, C., Ahlrichs, R.: Ab initio calculation of the vibrational and electronic spectra of trans- and cis-azobenzene. J. Am. Chem. Soc. 125, 9821–9827 (2003)

    Article  CAS  Google Scholar 

  21. Shimomura, M., Kunitake, T.: Fluorescence and photoisomerization of azobenzene-containing bilayer membranes. J. Am. Chem. Soc. 109, 5175–5183 (1987)

    Article  CAS  Google Scholar 

  22. Zhao, Y.: Light-responsive block copolymer micelles. Macromolecules 45, 3647–3657 (2012)

    Article  CAS  Google Scholar 

  23. Ho, M.S., Natansohn, A., Barrett, C., Rochon, P.: Azo polymers for reversible optical storage. 8. The effect of polarity of the azobenzene groups. Can. J. Chem. 73, 1773–1778 (1995)

    Article  CAS  Google Scholar 

  24. Gore, P.H., Wheeler, O.H.: Absorption spectra of aromatic azo and related compounds. III. Substituted azobenzenes. J. Org. Chem. 26, 3295–3298 (1961)

    Article  CAS  Google Scholar 

  25. Cook, A.H., Jones, D.G.: cis-Azo-compounds. J. Chem. Soc. 1309–1315 (1939)

    Google Scholar 

  26. Brode, W.R., Gould, J.H., Wyman, G.M.: The relation between the absorption spectra and the chemical constitution of dyes. XXVI. Effect of solvent and of temperature on the cis-trans isomerization of azo dyes. J. Am. Chem. Soc. 75, 1856–1859 (1953)

    Article  CAS  Google Scholar 

  27. Chen, P.C., Chieh, Y.C., Wu, J.C.: Theoretical study of the electronic spectra of azobenzene dyes. J. Mol. Struct.: THEOCHEM 715, 183–189 (2005)

    Article  CAS  Google Scholar 

  28. Briquet, L., Vercauteren, D.P., Perpète, E.A., Jacquemin, D.: Is solvent trans-azobenzene twisted of planer. Chem. Phys. Lett. 417, 190–195 (2006)

    Article  CAS  Google Scholar 

  29. Nishimura, N., Sueyoshi, T., Yamanaka, H., Imai, E., Yamamoto, S., Hasegawa, S.: Thermal cis-to-trans isomerization of substituted azobenzenes II. substituent and solvent effects. Bull. Chem. Soc. Jpn. 49, 1381–1387 (1976)

    Article  CAS  Google Scholar 

  30. Gabor, G., Fischer, E.: Spectra and cis-trans isomerization in highly bipolar derivatives of azobenzene. J. Phys. Chem. 75, 581–583 (1971)

    Article  CAS  Google Scholar 

  31. Cataliotti, R.S., Murgia, S.M., Paliani, G., Poletti, A., Zgierski, M.Z.: Resonances Raman scattering in Dyes derived from azobenzene. J. Raman Spectrosc. 16, 251–257 (1985)

    Article  CAS  Google Scholar 

  32. Rava, R.P.: Deconvoluting the visible absorption spectrum of methyl orange using inverse Raman transform techniques. J. Chem. Phys. 87, 3758–3765 (1987)

    Article  CAS  Google Scholar 

  33. Cataliotti, R.S., Morresi, A., Paliani, G., Zgierski, M.Z.: Resonances Raman scattering in azo dyes. J. Raman Spectrosc. 20, 601–604 (1989)

    Article  CAS  Google Scholar 

  34. Crecca, C.R., Roitberg, A.E.: Theoretical study of the isomerization mechanism of azobenzene and disubstituted azobenzene derivatives. J. Phys. Chem. A 110, 8188–8203 (2006)

    Article  CAS  Google Scholar 

  35. Cook, A.H.: The preparation of some cis-azo-compounds. J. Chem. Soc. 876–881 (1938)

    Google Scholar 

  36. Griffiths, J.: Photochemistry of azobenzene and its derivatives. Chem. Soc. Rev. 1, 481–493 (1972)

    Article  CAS  Google Scholar 

  37. Wildes, P.D., Pacifici, J.G., Irick Jr., G., Whitten, D.G.: Solvent and substituent effects on the thermal isomerization of substituted azobenzenes. A flash spectroscopic study. J. Am. Chem. Soc. 93, 2004–2008 (1971)

    Article  Google Scholar 

  38. Wu, L.F., Tuo, X.L., Cheng, H., Chen, Z., Wang, X.G.: Synthesis, photoresponsive behavior, and self-assembly of poly(acrylic acid)-based azo polyelectrolytes. Macromolecules 34, 8005–8013 (2001)

    Article  CAS  Google Scholar 

  39. Birnbaum, P.P., Style, D.W.G.: The photo-isomerization of some azobenzene derivatives. Trans. Faraday Soc. 50, 1192–1196 (1954)

    Article  CAS  Google Scholar 

  40. Lovrien, R., Waddington, J.C.B.: Photoresponsive systems. I. Photochromic macromolecules. J. Am. Chem. Soc. 86, 2315–2322 (1964)

    Article  CAS  Google Scholar 

  41. Ravve, A., Fitko, C.: Polymer formation through diazonium coupling. J. Polym. Sci. A 2, 1925–1940 (1964)

    Google Scholar 

  42. Kamogawa, H., Kato, M., Sugiyama, H.: Syntheses and properties of photochromic polymers of the azobenzene and thiazine series. J. Polym. Sci. A 6, 2967–2991 (1968)

    Article  CAS  Google Scholar 

  43. Williams, J.L.R., Daly, R.C.: Photochemical probes in polymers. Prog. Polym. Sci. 5, 61–93 (1977)

    Article  CAS  Google Scholar 

  44. Kumar, G.S., Neckers, D.C.: Photochemistry of azobenzene-containing polymers. Chem. Rev. 89, 1915–1925 (1989)

    Article  CAS  Google Scholar 

  45. Irie, M.: Properties and applications of photoresponsive polymers. Pure Appl. Chem. 62, 1495–1502 (1990)

    Article  CAS  Google Scholar 

  46. Xie, S., Natansohn, A., Rochon, P.: Recent developments in aromatic azo polymers research. Chem. Mater. 5, 403–411 (1993)

    Article  CAS  Google Scholar 

  47. Ichimura, K.: Photoalignment of liquid-crystal systems. Chem. Rev. 100, 1847–1873 (2000)

    Article  CAS  Google Scholar 

  48. Ikeda, T.: Photomodulation of liquid crystal orientations for photonic applications. J. Mater. Chem. 13, 2037–2057 (2003)

    Article  CAS  Google Scholar 

  49. Shibaev, V., Bobrovsky, A., Boiko, N.: Photoactive liquid crystal polymer systems with light-controlled structure and optical properties. Prog. Polym. Sci. 28, 729–836 (2003)

    Article  CAS  Google Scholar 

  50. Yu, Y.L., Ikeda, T.: Alignment modulation of azobenzene-containing liquid crystal systems by photochemical reactions. J. Photochem. Photobio. C 5, 247–265 (2004)

    Article  CAS  Google Scholar 

  51. Viswanathan, N.K., Kim, D.Y., Bian, S.P., Williams, J., Liu, W., Li, L., Samuelson, L., Kumar, J., Tripathy, S.K.: Surface relief structures on azo polymer films. J. Mater. Chem. 9, 1941–1955 (1999)

    Article  CAS  Google Scholar 

  52. Yager, K.G., Barrett, C.J.: All-optical patterning of azo polymer films. Curr. Opin. Solid State Mater. Sci. 5, 487–494 (2001)

    Article  CAS  Google Scholar 

  53. Natansohn, A., Rochon, P.: Photoinduced motions in azo-containing polymers. Chem. Rev. 102, 4139–4175 (2002)

    Article  CAS  Google Scholar 

  54. Delaire, J.A., Nakatani, K.: Linear and nonlinear optical properties of photochromic molecules and materials. Chem. Rev. 100, 1817–1845 (2000)

    Article  CAS  Google Scholar 

  55. Yesodha, S.K., Pillai, C.K.S., Tsutsumi, N.: Stable polymeric materials for nonlinear optics: a review based on azobenzene systems. Prog. Polym. Sci. 29, 45–74 (2004)

    Article  CAS  Google Scholar 

  56. Oliveira Jr., O.N., dos Santos Jr., D.S., Balogh, D.T., Zucolotto, V., Mendonca, C.R.: Optical storage and surface-relief gratings in azobenzene-containing nanostructured films. Adv. Colloid Interface Sci. 116, 179–192 (2005)

    Article  CAS  Google Scholar 

  57. Renner, C., Moroder, L.: Azobenzene as conformational switch in model peptides. ChemBioChem 7, 868–878 (2005)

    Article  Google Scholar 

  58. Yager, K.G., Barrett, C.J.: Novel photo-switching using azobenzene functional materials. J. Photochem. Photobio. A 182, 250–261 (2006)

    Article  CAS  Google Scholar 

  59. Ercole, F., Davis, T.P., Evans, R.A.: Photo-responsive systems and biomaterials: photochromic polymers, light-triggered self-assembly, surface modification, fluorescence modulation and beyond. Polym. Chem. 1, 37–54 (2010)

    Article  CAS  Google Scholar 

  60. Yu, Y.L., Ikeda, T.: Photodeformable polymers: a new kind of promising smart material for micro- and nano-applications. Macromol. Chem. Phys. 206, 1705–1708 (2005)

    Article  CAS  Google Scholar 

  61. Jiang, H.Y., Kelch, S., Lendlein, A.: Polymers move in response to light. Adv. Mater. 18, 1471–1475 (2006)

    Article  CAS  Google Scholar 

  62. Yu, H.F., Ikeda, T.: Photocontrollable liquid-crystalline actuators. Adv. Mater. 23, 2149–2180 (2011)

    Article  CAS  Google Scholar 

  63. Barrett, C.J., Mamiya, J.I., Yager, K.G., Ikeda, T.: Photo-mechanical effects in azobenzene-containing soft materials. Soft Matter. 3, 1249–1261 (2007)

    Article  CAS  Google Scholar 

  64. Seki, T.: Photoresponsive self-assembly motions in polymer thin films. Curr. Opin. Solid State Mater. Sci. 10, 241–248 (2006)

    Article  CAS  Google Scholar 

  65. Seki, T.: Smart photoresponsive polymer systems organized in two dimensions. Bull. Chem. Soc. Jpn. 80, 2084–2109 (2007)

    Article  CAS  Google Scholar 

  66. Seki, T., Nagano, S.: Light-directed dynamic structure formation and alignment in photoresponsive thin films. Chem. Lett. 37, 484–489 (2008)

    Article  CAS  Google Scholar 

  67. Wang, D.R., Wang, X.G.: Amphiphilic azo polymers: molecular engineering, self-assembly and photoresponsive properties. Prog. Polym. Sci. 38, 271–301 (2013)

    Article  CAS  Google Scholar 

  68. Shishido, A.: Rewritable holograms based on azobenzene-containing liquid-crystalline polymers. Polym. J. 42, 525–533 (2010)

    Article  CAS  Google Scholar 

  69. Lee, S.W., Kang, H.S., Park, J.K.: Directional photofluidization lithography: micro/nanostructural evolution by photofluidic motions of azobenzene materials. Adv. Mater. 24, 2069–2103 (2012)

    Article  CAS  Google Scholar 

  70. Priimage, A., Shevchenko, A.: Azopolymer-based micro- and nanopatterning for photonic applications. J. Polym. Sci. B. 52, 163–182 (2014)

    Article  Google Scholar 

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Wang, X. (2017). Introduction. In: Azo Polymers. Soft and Biological Matter. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53424-3_1

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