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Photochromic azo polysemicarbazides with biocompatibility behavior

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Abstract

Two kinds of azo polysemicarbazides were prepared based on 3, 3′-azobis (benzoylhydrazide) (ABH) and two kinds of diisocyanates via solution polymerization. The structures were characterized by Fourier-transform infrared (FT-IR) technique and elemental analysis. Inherent viscosities of the polymers were 0.32 and 0.29 dL/g and both could be dissolved in H2SO4 and polar organic solvents. Thermal gravimetric analysis (TGA) presented a multi-step degradation and a decomposition temperature range of 230–280 °C. And photoisomerization of the azo polymers in solvent of N, N-dimethyl acetamide (DMAc) was confirmed by Ultraviolet-visible spectroscopy (UV-Vis), suggested the isomerization appearing under the ultraviolet irradiation at 365 nm and recovering completely by visible light irradiation or kept in the dark. Transmission electron microscopy (TEM) of polysemicarbazides before and after soaking in bovine serum albumin (BSA) solution confirmed the biocompatibility of azo polymers.

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References

  1. Churikov V M, Hung M F. Real-time Monitoring of All-optical Poling of Azo-dye Polymer Thin Film[J]. Opt. Lett., 2000, 25: 960–962

    Article  CAS  Google Scholar 

  2. Aoshima Y, Egami C, Kawata Y, et al. Two-way Opticalmemory for Azobenzene-containing Urethane-urea Copolymer Films[J]. Opt. Commun., 1999, 165: 177–182

    Article  CAS  Google Scholar 

  3. Tirelli N, Solaro R A, Ciardelli F, et al. Structure-activity Relationship of New NLO Organic Materials Based on Push-pull Azo Dyes: Side Chain Polymers[J]. Polymer, 2000, 41: 415–421

    Article  CAS  Google Scholar 

  4. Andruzzi L, Altomare A, Ciardelli F, et al. Holographic Gratings in Azobenzene Side Chain Polymethacrylates[J]. Macromolecules, 1999, 32: 448–454

    Article  CAS  Google Scholar 

  5. Angiolini L, Caretti D, Giorgini L, et al. Optically Active Methacrylic Polymers Bearing Side-chain Conjugated Azoaromatic Chromophores[J]. Synth. Met., 2000, 115: 235–239

    Article  CAS  Google Scholar 

  6. Fiorini C, Charra F, Nunzi J M, et al. Photoinducednon Centrosymmetry in Azo-dye Polymers[J]. Nonlinear. Opt., 1995, 9: 339–347

    CAS  Google Scholar 

  7. Lee T S, Kim D Y, Jiang X L, et al. Photoinduced Surface Relief Gratings in High-Tg Main-chain Azoaromatic Polymer Films[J]. J. Polym. Sci., Part A: Polym. Chem., 1998, 36: 283–289

    Article  CAS  Google Scholar 

  8. Tracey M, David E G. Characterization of Azo Coupling Adducts of Benzenediazonium Ions with Aromatic Amino Acids in Peptides and Proteins[J]. Chem. Res. Toxicol., 1997, 10(12): 1378–1386

    Article  CAS  Google Scholar 

  9. Taiji I, Fumihiko H, Takashi M, et al. Molecula-Shape Imprinting and Immobilization of Biomolecules on a Polymer Containing Azo Dye[J]. Langmuir, 2006, 22: 2747–2753

    Article  Google Scholar 

  10. Parra S, Nadtotechenko V, Albers P, et al. Discoloration of Azo-Dyes at Biocompatible pH-Values through an Fe-Histidine Complex Immobilized on Nafion via Fenton-like Processes[J]. J. Phys. Chem. B, 2004, 108: 4439–4448

    Article  CAS  Google Scholar 

  11. Vollmer M S, Clark T D, Steinem C M, et al. Photoswitchable Hydrogen-Bonding in Self-Organized Cylindrical Peptide Systems[J]. Angewandte Chemie International Edition, 1999, 38(6): 1598–1601

    Article  CAS  Google Scholar 

  12. Ven D, Mooter G, Maris B, et al. Use of Azo Polymers for Colon-specific Drug Delivery[J]. J. Phar. Sci., 1997, 6 (12): 1321–1327

    Google Scholar 

  13. Vale R O, Milligan R A. The Way Things Move: Looking Under The Hood of Molecular Motor Proteins[J]. Science, 2002, 288: 88–95

    Article  Google Scholar 

  14. Hugel T, Holland N B, Cattani A, et al. Single-molecule Optomechanical Cycle[J]. Science, 2002, 296: 1103–1106

    Article  Google Scholar 

  15. Holland N B, Hugel T, Neuert G, et al. Single Molecule Force Spectroscopy of Azobenzene Polymers: Switching Elasticity of Single Photochromic Macromolecules[J]. Macromolecules, 2003, 36(6): 2015–2023

    Article  CAS  Google Scholar 

  16. Frazer A H and Wallenberger F T. Aliphatic Polyhydrazides: A New Low Temperature Solution Polymerization[J]. Polym. Sci. Part A. Polym. Chem., 1964, 2: 1137–1146

    CAS  Google Scholar 

  17. Frazer A H and Wallenberger F T. Aromatic Polyhydrazides: A New Class of Highly Bonded, Stiff Polymers[J]. J. Polym. Sci. Part A., Polym. Chem., 1964, 2: 1147–1156

    CAS  Google Scholar 

  18. Frazer A H, Sweeny W, Wallenberger F T. Poly(1, 3, 4-oxadiazole) Fibers: New Fibers With Superior High Temperature Resistance[J]. J. Polym. Sci. Part A., Polym. Chem., 1964, 2: 1157–1165

    CAS  Google Scholar 

  19. Campbell T W, Foldi V S, Farago J. Condensation Polymers From Diisocyanates with Dihydrazides and Hydrazine[J]. J. Appl. Polym. Sci., 1959, 2: 155–162

    Article  CAS  Google Scholar 

  20. Cao L H, Zhou C J, Liu Y T, et al. The Synthesis of N-(Glycosylthioureylene)-aminothiophosphonic and -diaminoth-ophos-phinic O-aryl Esters[J]. Chem. Soc., 2001, 48(2): 207–210

    CAS  Google Scholar 

  21. Abdellatif G, Imam H. A Study of The Laser Plasma Parameters at Different Laser Wavelengths[J]. Spectrchimica. Acta. Part B, 2002, 57: 1155–1165

    Article  Google Scholar 

  22. Ruijtzer K, John A W, Lefebe D J, et al. Approaches to the Synthesis of Ureapeptoid Peptidomimetics[J]. Tetrahedron. lett., 1997, 38: 5335–5338

    Article  Google Scholar 

  23. Wang X C, Li Z, Da Y X, et al. A Facile Method to 1,4-diacylsemicarbazides: Synthesis of 1-aryloxyacetyl-4-(4-chlorobenzoyl)-thiosemicarbazides and Semicarbazides[J]. Synth. Commun., 2000, 30(18): 3405–3411

    Article  CAS  Google Scholar 

  24. Molina P, Tarraga A, Lopez J L, et al. Preparation and Heterocyclization Reactions of Ferrocenylazido Ketones. Useful Building Blocks for the Synthesis of Ferrocenyl-substituted Azaheterocycles[J]. Organomet. Chem., 1999, 584: 147–158

    CAS  Google Scholar 

  25. Chohan Z H, Pervez H, Kausar S, et al. Synthesis and Characterization of Antibacterial Co(II), Cu(II), Ni(II), and Zn(II) Complexes of Acylhydrazine Derived Pyrrolyl Compounds[J]. Synth. React. Inorg. Met.Org. Chem., 2002, 32: 529–543

    Article  CAS  Google Scholar 

  26. Vogel A I. Text Book of Practical Organic Chemistry[M]. 5th ed. Addison Wesley Longman Ltd, Essex, 1996

    Google Scholar 

  27. Aruna P, Venkateshwarlu U, Ganga R. Thermal and Mechanical Properties of Fiber-forming Poly(urethane semicarbazide) s[J]. J. Appl. Polym. Sci., 2002, 83: 86–93

    Article  Google Scholar 

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Authors and Affiliations

  1. School of Materials Science and Engineering, Wuhan University of Technology, Wuhan, 430070, China

    Yun Liu  (刘芸), Chuanxi Xiong  (熊传溪), Lijie Dong, Yongsheng Niu, Liping Liu & Qingming Zhu

  2. State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan, 430070, China

    Chuanxi Xiong  (熊传溪) & Lijie Dong

Authors
  1. Yun Liu  (刘芸)
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  2. Chuanxi Xiong  (熊传溪)
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  3. Lijie Dong
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  4. Yongsheng Niu
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  5. Liping Liu
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  6. Qingming Zhu
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Corresponding author

Correspondence to Chuanxi Xiong  (熊传溪).

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Funded by the National Natural Science Foundation of China (No. 50572081)

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Liu, Y., Xiong, C., Dong, L. et al. Photochromic azo polysemicarbazides with biocompatibility behavior. J. Wuhan Univ. Technol.-Mat. Sci. Edit. 25, 979–983 (2010). https://doi.org/10.1007/s11595-010-0133-9

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  • DOI: https://doi.org/10.1007/s11595-010-0133-9

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