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Synthesis and characterization of novel AZO chromophore with multi hydroxyl groups

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Abstract

Novel organic second order nonlinear optical chromophore with 4,4′-(5-(bis(2-hydroxyethyl)amino)-1,3-phenylene)bis(oxy)dibutan-1-ol as electron donor and azo thiophene as π-electronic bridge was synthesized and characterized by 1H NMR spectra and mass spectra. After the introduction of four hydroxyl groups to the electron donor, the solubility of chromophore Z1 in water was improved greatly (0.5 g). Else, the solubility of chromophore Z1 in common organic solvents was still very good. The thermal decomposition temperature was above 250 °C, which was high enough for its application in both the preparation of optoelectronic devices and Second harmonic generation imaging. Electro-optical films prepared by chromophore Z1 showed us the largest second-order nonlinear optical coefficient was about 85 pm/V, which was large enough for the detection of second harmonic generation signal in water solution. Else, the photochemical stability of chromophore Z1 was also studied; the advantage of chromophore with azo bond was very obvious for improving the photochemical stability of organic second order nonlinear optical chromophores.

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Acknowledgments

We are grateful to science and technology innovation project of Chinese Academy of Agricultural Sciences for financial support. And thanks for Dr. Zhang H in University of Electronic Science and technology for measurement of the polymers’ SHG characters.

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Authors and Affiliations

  1. Institute of Quality Standards and Testing Technology for Agro-Products/Key Laboratory of Agro-Product Quality and Safety, Chinese Academy of Agriculture Sciences, Beijing, 100081, People’s Republic of China

    Jian Zhou & Min Wang

  2. Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, People’s Republic of China

    Hui Yang

  3. Institute of Basic Medicine, SAMS, Jinan, 250062, Shandong Province, People’s Republic of China

    Xiaobing Li

Authors
  1. Jian Zhou
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  2. Hui Yang
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  3. Xiaobing Li
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  4. Min Wang
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Correspondence to Xiaobing Li or Min Wang.

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Zhou, J., Yang, H., Li, X. et al. Synthesis and characterization of novel AZO chromophore with multi hydroxyl groups. J Mater Sci: Mater Electron 27, 2189–2194 (2016). https://doi.org/10.1007/s10854-015-4009-9

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  • DOI: https://doi.org/10.1007/s10854-015-4009-9

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