Home Designing, characterization, and thermal behavior of triazine-based dendrimers
Article
Licensed
Unlicensed Requires Authentication

Designing, characterization, and thermal behavior of triazine-based dendrimers

  • Dhaval G. Gajjar , Rinkesh M. Patel , Hema N. Patel and Pravinkumar M. Patel EMAIL logo
Published/Copyright: September 17, 2014
Become an author with De Gruyter Brill

Abstract

Different generations of dendritic architecture with piperazine in core moiety and hydroxyl groups on the periphery were designed by divergent method. 1,4-biz(4,6-trichloro-1,3,5-triazin-2-yl)piperazine was synthesized as a core for dendrimer synthesis. Dendrimer was then grown to G3 from core compound using diethanolamine and cyanuric chloride as branching units. Dendrimer generations were characterized by infrared (IR) spectroscopy [Fourier transform IR (FTIR)], 1H-nuclear magnetic resonance (NMR), 13C-NMR, electrospray ionization-mass spectrometry (ESI-MS), and elemental analysis. The thermal behavior of both full- and half-generation dendrimers was investigated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The TGA study revealed that dendrimer generations had a moderate thermal stability. Chlorine-terminated half-generation dendrimers were thermally more stable than hydroxyl-terminated full-generation dendrimers. The DSC technique was employed to determine the glass transition temperatures (Tg) of dendrimer generations. It was observed that the glass transition temperatures of synthesized dendrimer generations were of low value, which is similar to the values reported for the polyamidoamine (PAMAM) dendrimer of the same generation. It was also observed that, with the increase in the molecular weight or generation number of dendrimer, the glass transition temperature was also increased.


Corresponding author: Pravinkumar M. Patel, Industrial Chemistry Department, V.P. & R.P.T.P. Science College (affiliated to Sardar Patel University), Vallabh Vidhyanagar 388120, Gujarat, India, e-mail:

Acknowledgments

The authors are grateful to The Principal, V.P. & R.P.T.P. Science College, for providing laboratory facility. The authors are also grateful to U.G.C. New Delhi for funding this research work. The authors acknowledge the Sophisticated Analytical Instrumentation Facility (SAIF), Punjab University, Chandigarh, the Sophisticated Instrumentation Centre for Advanced Research and Testing (SICART), Vallabh Vidhyanagar, and the Central Salt and Marine Chemicals Research Institute (CSMCRI) providing the instrumentation facilities.

References

[1] Tomalia DA. Aldrichim. Acta 2004, 37, 39–57.10.1080/713854236Search in Google Scholar

[2] Simanek EE, Abdou H, Lalwani S, Lim J, Mintzer M, Venditto V, Vittur B. Proc. R. Soc. A 2010, 466, 1445–1468.10.1098/rspa.2009.0108Search in Google Scholar

[3] Lai L-L, Hsieh J-W, Cheng K-L, Liu S-H, Lee J-J, Hsu H-F. Chem. Eur. J. 2014, 20, 5160–5166.Search in Google Scholar

[4] Zhang W, Simanek EE. Tetrahedron Lett. 2001, 42, 5355–5357.Search in Google Scholar

[5] Mintzer MA, Merkel OM, Kissel T, Simanek EE. N. J. Chem. 2009, 33, 1918–1925.Search in Google Scholar

[6] Rothmann MM, Haneder S, Da Como E, Lennartz C, Schildknecht C, Strohriegl P. Chem. Mater. 2010, 22, 2403–2410.Search in Google Scholar

[7] Maiti SK, Jardim MG, Rodrigues J, Rissanen K, Campo J, Wenseelers W. Organomettalics 2013, 32, 406–414.10.1021/om300745vSearch in Google Scholar

[8] Chan-Thaw CE, Villa A, Katekomol P, Su D, Thomas A, Prati L. Nano Lett. 2010, 10, 537–541.Search in Google Scholar

[9] Gajjar D, Patel R, Patel H, Patel PM. Int. J. Pharm. Pharm. Sci. 2014, 6, 357–361.Search in Google Scholar

[10] Patel R, Gajjar D, Patel H, Patel PM. Asian J. Pharm. Clin. Res. 2014, 7, 156–161.Search in Google Scholar

[11] Gajjar D, Patel R, Patel H, Patel PM. Chem. Sci. Trans. 2014, 3, 897–908.Search in Google Scholar

[12] Miyashita K, Pauling L. J. Org. Chem. 1976, 41, 2032–2034.Search in Google Scholar

[13] Blotny G. Tetrahedron 2006, 62, 9507–9522.10.1016/j.tet.2006.07.039Search in Google Scholar

[14] Johnson A. The Theory of Colourisation of Textile Society of Dyes and Colourists. Society of Dyers and Colourist, Bradford, UK, 1989.Search in Google Scholar

[15] Nishimura N, Kato A. Carbohydr. Res. 2001, 331, 77–82.Search in Google Scholar

[16] Venkataraman K, Wagle DR. Tetrahedron Lett. 1979, 20, 3037–3040.Search in Google Scholar

[17] Young KL, Xu C, Xie J, Sun S. J. Mater. Chem. 2009, 19, 6400–6406.Search in Google Scholar

[18] Zhang W, Jiang J, Qin C, Thomson LM, Parrish AR, Safe SH, Simanek EE. Supramol. Chem. 2003, 15, 607–616.Search in Google Scholar

[19] Lim J, Simanek EE. Adv. Drug Deliv. Rev. 2012, 64, 826–835.Search in Google Scholar

[20] Bansal KK, Kakde D, Gupta U, Jain NK. J. Nanosci. Nanotechnol. 2010, 10, 8395–8404.Search in Google Scholar

[21] Kraus GA, Louw SVJ. Org. Chem. 1998, 63, 7520–7521.Search in Google Scholar

[22] Zhang W, Simanek EE. Org. Lett. 2000, 2, 843–845.Search in Google Scholar

[23] Dreyer C, Blume A, Bauer M, Bauer J, Neumann-Rodekirch J. Triazine based dendrimers. In: Fourth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-4), Switzerland, a0098, 2000.10.3390/ecsoc-4-01879Search in Google Scholar

[24] Tomalia DA. Prog. Polym. Sci. 2005, 30, 294–324.Search in Google Scholar

[25] Huang H, Dong CM, Wei Y. Comb. Chem. High Throughput Screen. 2007, 10, 368–376.Search in Google Scholar

[26] Zheng P, Gao L, Sun X, Mei S. Iran. Polym. J. 2009, 18, 257–264.Search in Google Scholar

[27] Wooley KL, Hawker CJ, Pochan JM, Frechet JMJ. Macromolecules 1993, 26, 1514–1519.10.1021/ma00059a006Search in Google Scholar

[28] Lin X, Zhou J, Xu D. Chin. J. Chem. 2012, 30, 1485–1489.Search in Google Scholar

[29] Singh M, Gupta S. Synth. Commun. 2008, 38, 2898–2907.Search in Google Scholar

[30] Namazi H, Adeli M. Polymer 2005, 46, 10788–10799.10.1016/j.polymer.2005.09.020Search in Google Scholar

[31] Didehban K, Namazi H, Entezami AA. Iran. Polym. J. 2009, 18, 731–741.Search in Google Scholar

[32] Uppuluri S, Dvornic PR, Tan NCB, Hagnauer G. The Properties of Dendritic Polymers 2: Generation Dependence of the Physical Properties of Poly (Amidoamine) Dendrimers. No. ARL-TR-1774. Army Research Lab, Aberdeen Proving Ground MD, 1999.10.21236/ADA359423Search in Google Scholar

[33] Doyle CD. Anal. Chem. 1961, 33, 77–79.Search in Google Scholar

[34] Antoni P, Robb MJ, Campos L, Montanez M, Hult A, Malmstrom E, Malkoch M, Hawker CJ. Macromolecules 2010, 43, 6625–6631.10.1021/ma101242uSearch in Google Scholar


Supplemental Material

The online version of this article (DOI: 10.1515/polyeng-2014-0123) offers supplementary material, available to authorized users.


Received: 2014-5-6
Accepted: 2014-7-26
Published Online: 2014-9-17
Published in Print: 2015-1-1

©2015 by De Gruyter

Downloaded on 24.9.2025 from https://www.degruyterbrill.com/document/doi/10.1515/polyeng-2014-0123/html
Scroll to top button