Thermal stability of second generation carbosilane dendrimers with peripheral ammonia groups
Source abstract
Abstract
Thermal analysis has a wide range of applications in pharmaceutical industry, in designing new molecules, control of raw materials, stability, compatibility studies, and development of new formulations. This paper evaluates the thermodynamic properties of two second generation G2 carbosilane dendrimers with peripheral ammonia groups by differential scanning calorimetry and TG/FTIR coupled techniques. The physical transformations have been detected and their thermodynamic characteristics have been estimated and analyzed. Both dendrimers are stable up to 150 °C, have the Tg at 75 and 59 °C and melting temperatures at 113 and 128 °C, respectively. The decomposition process proved to be very complex and takes place in three steps in nitrogen atmosphere and four steps in air, for both types of dendrimers. IR spectroscopic analysis was used to observe the evolution of the gaseous products versus temperature.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Dendrimers and Hyperbranched Polymers · Synthesis and properties of polymers · Ferrocene Chemistry and Applications
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (36)
Show source-provided references
1. Benito JM, de Jesus E, de la Mata FJ, Flores JC, Gomez R (2008) Carbosilane dendrimers containing complexes N,N0-pyridylimine of molybdenum and platinum at their periphery. J Organomet Chem 693:278–28210.1016/j.jorganchem.2007.10.050 ↗
2. Bobrovsky Y, Pakhomov AA, Zhu X-M, Boiko NI, Shibaev VP, aStumpe J (2002) Photochemical and photoorientational behavior of liquid crystalline carbosilane dendrimer with azobenzene terminal groups. J Phys Chem B 106:540–54610.1021/jp0125247 ↗
3. Buschbeck R, Lang H (2004) Triethylene glycol ether end-grafted carbosilanedendrimers: synthesis and complexation behaviour. Inorg Chem Commun 7:1213–121610.1016/j.inoche.2004.08.023 ↗
4. Chauhan AS, Sridevi S, Chalasani KB, Jain AK, Jain SK, Jain NK, Diwan PV (2003) Dendrimer-mediated transdermal delivery: enhanced bioavailability of indomethacin. J Control Release 90:335–34310.1016/S0168-3659(03)00200-1 ↗
5. Chou C-M, Lien H-L (2011) Dendrimer-conjugated magnetic nanoparticles for removal of zinc (II) from aqueous solutions. J Nanopart Res 13:2099–210710.1007/s11051-010-9967-5 ↗
6. Craig DQM, Reading M (2006) Thermal analysis of pharmaceuticals. CRC Press Taylor & Francis Group, New York10.1201/9781420014891 ↗
7. de la Cuevas N, Garcia-Gallego S, Rasines B, de la Mata FJ, Guijarro LG, Muñoz Fernández MA, Gómez R (2012) In vitro studies of water-stable cationic carbosilane dendrimers as delivery vehicles for gene therapy against HIV and hepatocarcinoma. Curr Med Chem 19:5052–506110.2174/0929867311209025052 ↗
8. Fernandes DM, Hechenleitner AAW, Gomez Pineda EA (2006) Kinetic study of the thermal decomposition of poly(vinyl alcohol)/kraft lignin derivative blends. Thermochim Acta 441:101–10910.1016/j.tca.2005.11.006 ↗
9. Fernández MD, Fernández MJ (2008) Thermal degradation of copolymers from vinyl acetate and vinyl alcohol. J Therm Anal Calorim 92(3):829–837. doi: 10.1007/s10973-007-8780-610.1007/s10973-007-8780-6 ↗
10. Frechet JM, Tomalia DA (2001) Dendrimers and other dendritic polymers. Wiley, New York10.1002/0470845821 ↗
11. Genson KL, Holzmueller J, Leshchiner I, Agina E, Boiko N, Shibaev VP, Tsukruk VV (2005) Organized monolayers of carbosilane dendrimers with mesogenic terminal groups. Macromolecules 38:8028–803510.1021/ma050304b ↗
12. Giron D (2002) Applications of thermal analysis and coupled techniques in pharmaceutical industry. J Therm Anal Calorim 68(2):335–35710.1023/A:1016015113795 ↗
13. Johnson DJ (1988) Solvent retention studies for pharmaceutical samples using an integrated TGA/FT-IR system. Compton DAC Spectrosc 3:47–50
14. Kannan S, Kolhe P, Raykova V, Glibatec M, Kannan RM, Lieh-Lai M, Bassett D (2004) Dynamics of cellular entry and drug delivery by dendritic polymers into human lung epithelial carcinoma cells. J Biomater Sci Polym Ed 15:311–33010.1163/156856204322977201 ↗
15. Lebedev BV, Ryabkov M, Tatarinova EA, Rebrov EA, Muzafarov AM (2003a) Thermodynamic properties of the first to fifth generations of carbosilane dendrimers with allyl terminal groups. Russ Chem Bull 52(3):545–55110.1023/A:1023977916394 ↗
16. Lebedev BV, Kulagina TG, Ryabkov MV, Ponomarenko SA, Makeev EA, Boikov NI, Shibaev VP, Rebrov EA, Muzafarov AM (2003b) Carbosilane dendrimer of second generation with terminal methoxyundecylenate groups. J Therm Anal Calorim 71(2):481–49210.1023/A:1022895624502 ↗
17. Lorenz K, Hölter D, Stühn B, Mülhaupt R, Frey H (1996) A mesogen-functionized carbosilane dendrimer: a dendritic liquid crystalline polymer. Adv Mater 8:414–41610.1002/adma.19960080509 ↗
18. Lorenz K, Frey H, Stuhn B, Mulhaupt R (1997) Carbosilane dendrimers with perfluoroalkyl end groups. core-shell macromolecules with generation-dependent order. Macromolecules 30:6860–686810.1021/ma970282w ↗
19. Markin AV, YaS Samosudova, Smirnova NN, Tatarinova EA, Bystrova AV, Muzafarov AM (2011) Thermodynamics of carbosilane dendrimers with diundecylsilyl and diundecylsiloxane terminal groups. J Therm Anal Calorim 105(2):663–67610.1007/s10973-010-1199-5 ↗
20. Materazzi S (1997) Thermogravimetry-infrared spectroscopy (TG-FTIR) coupled analysis. Appl Spec Rev 32(4):385–404. doi: 10.1080/0570492970800332010.1080/05704929708003320 ↗
21. Oka H, Onaga T, Koyama T, Guo C-T, Suzuki Y, Esumi Y, Hatano K, Terunuma D, Matsuoka K (2009) Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyla(2→3) lactose moieties as inhibitors for human influenza viruses. Bioorg Med Chem 17:5465–547510.1016/j.bmc.2009.06.035 ↗
22. Omotowa BA, Shreeve JM (2003) Preparation, characterization, and thermal and surfactant studies of polyfluorinated amphiphilic carbosilane dendrimers. Macromolecules 36:8336–834510.1021/ma034326e ↗
23. Popescu M-C, Gomez R, de la Mara FJ, Rasines B, Simionecu BC (2013) Characterization by fourier transform infrared spectroscopy (FT-IR) and 2D IR correlation spectroscopy of a carbosilane dendrimer with peripheral ammonium groups. J Nanopart Res 15:1713. doi: 10.1007/s11051-013-1713-310.1007/s11051-013-1713-3 ↗
24. Rasines B, Hernandez-Ros JM, de las Cuevas N, Copa-Patiño JL, Soliveri J, Muñoz-Fernandez MA, Gómez R, de la Mata FJ (2009) Water-stable ammonium-terminated carbosilane dendrimers as efficient antibacterial agents. Dalton Trans 40:8704–871310.1039/b909955g ↗
25. Rasines B, Sánchez-Nieves J, Molina IT, Guzman M, Muñoz Fernández MaA, Gómez R, de la Mata FJ (2012) Synthesis and fluorescent properties of cationic carbosilane dendrimers containing eugenol linkers for their use in biomedical applications. New J Chem 36:360–37010.1039/C1NJ20374F ↗
26. Roovers J, Ding J (2009) In: Dvornic PR, Owen MJ (eds) Silicon-containing dendritic polymers. Springer, New York
27. Ryabkov MV, Kulagina TG, Lebedev BV (2001) The thermodynamic properties of carbosilane dendrimers of the first and second generation with terminal allyl groups in the temperature range 0–340 K. Zh Fiz Khim 75:2165–2173
28. Sakamoto J-I, Koyam T, Miyamot D, Yingsakmongkon S, Hidari KIPJ, Jampangern W, Suzuki T, Suzuki Y, Esumi Y, Nakamura T, Hatano K, Terunuma D, Matsuoka K (2009) Systematic syntheses of influenza neuraminidase inhibitors: a series of carbosilane dendrimers uniformly functionalized with thioglycoside-type sialic acid moieties. Bioorg Med Chem 17:5451–546410.1016/j.bmc.2009.06.036 ↗
29. Shumilkina NA, Myakushev VD, Tatarinova EA, Buzin MI, Voronina NV, Laptinskaya TV, Galyamov MO, Khokhlov AR, Muzafarov AM (2006) Synthesis and properties of fluorinated derivatives of carbosilane dendrimers of high generations. Polym Sci Series A 48(12):1240–124710.1134/S0965545X06120030 ↗
30. Smirnova NN, Stepanova OV, Bykova TA, Muzafarov AM, Tatarinova EA, Myakushev VD (2006) Thermodynamic properties of carbosilane dendrimers of the third to the sixth generations with terminal butyl groups in the range from T → 0 to 600 K. Thermochim Acta 440:188–19410.1016/j.tca.2005.11.009 ↗
31. Smirnova NN, Stepanova OV, Bykova TA, Markin AV, Tatarinova EA, Muzafarov AM (2007) Thermodynamic properties of carbosilane dendrimers of the seventh and ninth generations with terminal butyl groups in the temperature range from T → 0 to 600 K. Russ Chem Bull 56:1991–199510.1007/s11172-007-0310-y ↗
32. Smirnova NN, Markin AV, Samosudova YaS, Ignateva GM, Muzafarov AM (2010) Thermodynamics of a seventh generation carbosilane dendrimer with phenylic substituent on the initial branching center and terminal butyl groups. Russ J Phys Chem A 84(5):784–79110.1134/S0036024410050134 ↗
33. Sun WY, Lu HF, Wang DX, Feng SY (2009) A series of carbosilane dendrimers with acetyl end-group: from synthesis to their unique optical characteristics. Chin Chem Lett 20:1085–108710.1016/j.cclet.2009.05.016 ↗
34. Wiwattanapatapee R, Jee RD, Duncan R (1999) PAMAM dendrimers as a potential oral drug delivery system: dendrimer complexes with piroxicam. Proc Int Symp Control Release Bioact Mater 26:145–146
35. Yellepeddi VK, Vangara KK, Palakurthi S (2013) Poly(amido)amine (PAMAM) dendrimer–cisplatin complexes for chemotherapy of cisplatin-resistant ovarian cancer cells. J Nanopart Res 15:189710.1007/s11051-013-1897-6 ↗
36. Yoo H, Sazani P, Juliano RL (1999) PAMAM dendrimers as delivery agents for antisense oligonucleotides. Pharm Res 16(12):1799–180410.1023/A:1018926605871 ↗