The Synthesis of Poly(amidoamine) Dendrimer: Dyeing and Fluorescence Properties

Document Type : Original Article

Authors

1 Department of Organic Colorants, Institute for Color Science and Technology, P.O. Box: 16765-654, Tehran, Iran.

2 Department of Organic Colorants, Institute for Color Science and Technology, P.O. Box: 16765-654, Tehran, Iran

3 Center of Excellence for Color Science and Technology, Institute for Color Science and Technology, P.O. Box: 16765-654, Tehran, Iran.

Abstract

The synthesis of a new yellow fluorescent 4-(2-methylamino)-ethyloxy-N-PAMAM-1,8-naphthalimide from zero generation has been described. The chemical structure of synthesized dendrimers was confirmed using FT-IR, 1HNMR and DSC techniques. The new materials are comprised of a 1,8-naphthalimide fluorophore having a substituent at C-4 position. The synthesized compounds (P2 and P3) were used for dyeing of wool fibers. The physical properties of the compounds (P2 andP3) were also investigated via fastness measurement.

Keywords

References

  1. M. Sadeghi-Kiakhani, A. R. Tehrani-Bagha, Retarding action of poly (amidoamine) dendrimers and cationic gemini surfactants in acrylic dyeing, Dye Pigm., 125(2016), 323-330.
  2. X. Fei, Y. Gu, Y. Lan, B. Shi, Fluorescent properties of novel dendrimer dyes based on thiazole orange, J. Lumines., 131(2011), 2148-2152.
  3. M. Jikei, M. Kakimoto, Hyperbranched polymers: a promising new class of materials, Prog. Polym. Sci., 26(2001), 1233-1285.
  4. T. Okamoto, A. Momotake, Y. Shinohara, R. Nagahata, T. Arai, Isomer Specific Solvent Effect on Photoisomerization of Photoresponsive Polyphenylene Dendrimers with a Stilbene Core, Bull. Chem. Soc. Jpn., 80(2007), 2226-2228.
  5. C. J. Gabriel, J. R. Parquette, Expanding Dendrons. The Photoisomerism of Folded Azobenzene Dendrons, J. Am. Chem. Soc., 128(2006), 13708-10709.
  6. Y. Fujimoto, T. Ubukata, Y. Yokoyama, Dendrimer diarylethenes: the memory effect of conformation in polymer matrices, Chem. Commun., (2008), 5755-5757.
  7. T. Sajed, A. Haji, M. Khajeh Mehrizi, M. Nasiri Boromand, Modification of wool protein fiber with plasma and dendrimer: Effects on dyeing with cochineal, Inter. J. Biol. Macromol., 107(2018) 642-653.
  8. S.M. Burkinshaw, M Mignanelli, P.E. Froehling, M.J. Bide, The use of dendrimers to modify the dyeing behaviour of reactive dyes on cotton, Dye Pigment., 47(2000), 259-267.
  9. A. A. Zolriasatein, M. E. Yazdanshenas, R. Khajavi, The application of poly(amidoamine) dendrimers for modification of jute yarns: Preparation and dyeing properties, J. Saudi Chem. Rev., (2012), doi:10.1016/j.jscs.2012.01.007.
  10. F. Khakzar, R. M. A. Malek, F. Mazaheri, The effect of dendrimer on cotton dyeability with direct dyes, Chem. Ind. Chem. Eng. Q., 20 (2011) 379-385.
  11. F. Zheng, Y. Chen, H. Lin, Y. Lu, Synthesis of an amino-terminated hyperbranched polymer and its application in reactive dyeing on cotton as a salt-free dyeing auxiliary, Color Technol., 123(2007), 351-357.
  12. M. Sadeghi-Kiakhani, S. Safapour, Salt-free dyeing of cotton fabric modified with prepared chitosan-poly (propylene) imine dendrimer using direct dyes, Prog. Color Colorants Coat., 11(2018), 21-32.
  13. M. Dodangeh, K. Gharanjig, M. Arami, Synthesis, characterization, and photo-physical properties of dendrimers modified with 1,8-naphthalimide derivatives as novel Fluorescent pH Sensors, IEEE Sensor J., 14(2014), 2889-2896.
  14. I. Grabchev, X. Qian, V. Bojinov, Y. Xiao, and W. Zhang, Synthesis and photophysical properties of 1,8-naphthalimide-labelled PAMAM as PET sensors of protons and of transition metal ions, Polym., 43(2002), 5731–5736.
  15. S. Yordanova, I. Grabchev, S. Stoyanov, I. Petkov, New detectors for metal cations and protons based on PAMAMdendrimers modified with 1,8-naphthalimide, J. Photochem. Photobiol. A Chem., 283(2014), 1-7.
  16. M. Liang, K. Wang, R. Guan, Z. Liu, D. Cao, Q. Wu, Y. Shan, Y. Xu, Several hemicyanine dyes as fluorescence chemosensors for cyanide anions, Spectrochimica Acta A Mol. Biomol. Spect., 160(2016), 34-38.
  17. I. Grachev, S. Dumas, J. Chovelon, A. Nedelcheva, First generation poly(propyleneimine) dendrimers functionalized with 1,8-naphthalimide units as fluorescence sensors for metal cations and protons, Tetrahedron, 64(2008), 2113-2119.
  18. M. Hosseinnezhad, A. Khosravi, K. Gharanjig, S. Moradian, The comparison of spectra and dyeing properties of new azonaphthalimide with analogues azobenzene dyes on natural and synthetic polymers, Arabian. J. Chem., 10(2017), S3284-S3291.
  19. I. Grachev, J. Chovelon, V. Bojinov, G. Ivanova, Poly(amidoamine) dendrimers peripherally modified with 4-ethylamino-1,8-naphthalimide: synthesis and photophysical properties, Tetrahedron, 59(2003), 95-91-9598.
  20. Y. Li, L. Cao, H. Tian, Fluoride ion-triggered dual fluorescence switchbased on naphthalimides winged zinc porphyrin, J. Org. Chem., 71(2006), 8279-8282.
  21. J. Y. Kim, C. Sakong, S. Choi, H. Jang, S. H. Kim, K. Seong Chang, M. S. Han, J. S. Lee, J. Pil Kim, The effect of fluorescence of perylene red dyes on the contrast ratio of LCD color filters, Dye Pigm., 131(2016), 293-300.
  22. M. Hosseinnezhad, S. Rouhani, Characteristics of nanostructure dye-sensitized solar cells using food dyes, Opto-Electron. Rev., 24(2016), 34-39.
  23. H. Cao, V. Chang, R. Hernandez, M. D. Heagy, Matrix screening of substituted N-aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually brightpyridine derivatives, J. Org. Chem., 70(2005), 4929-4934.
  24. M. Paula Militello, R. E. Hernández-Ramírez, I. V. Lijanova, C.M. Previtali, S.G. Bertolotti, E.M. Arbeloa, Novel PAMAM dendrimers with porphyrin core as potential photosensitizers for PDT applications, J. Photochem. Photobiol. A Chem., 353(2018), 71-76
Progress in Color, Colorants and Coatings
Volume 11, Issue 3
July 2018
Pages 173-178

Files

Share

How to cite

Statistics