The Synthesis of Polyamidoamine Dendrimer: Dyeing and Fluorescence Properties




Article Code:
PCCC-2018-03-23-379

Authors:
Mohammad Dodangeh: Institute of Color Science and Technology - Department of Organic Colorants
K. Gharanjig: Institute for Color Science and Technology - Center of Excellence for Color Science and Technology,Department of Organic Colorants
M. Hosseinnezhad: Institute for Color Science and Technology - Center of Excellence for Color Science and Technology,Department of Organic Colorants


Article's 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 structures of synthesized dendrimers were confirmed using FTIR, 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 was used for dyeing of wool fibers. The physical properties of the compounds P2 and P3 were performed by fastness measurement.


Keywords:
1,8-naphthalimide, polyamidoamine dendrimer, Fluorescence, Dyeing, Fastness

References:
[1] M. Sadeghi-Kiakhani, A.R. Tehrani-Bagha, Retarding action of poly(amidoamine) dendrimers and cationic gemini surfactants in acrylic dyeing, Dye Pigment, 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, Polymer, 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] 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. [19] Y. Li, L. Cao, H. Tian, Fluoride ion-triggered dual fluorescence switchbased on naphthalimides winged zinc porphyrin, J. Org. Chem., 71(2006), 8279-8282. [20] 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 Pigment, 131(2016), 293-300. [21] 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. [22] 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.


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