Restricted accessResearch articleFirst published online 2013-9
Investigating thermophysical properties of novel chiral nanostructured poly(amide-ester-imide)s containing different amino acids based on biological active N,N ′-(pyromellitoyl)-bis- l -amino acids and diol
Preparation of potentially biodegradable poly(amide-ester-imide)s (PAEI)s with different amino acids was described. For the first time, the synthesis of diol N, N′-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6(1H,3H)-diyl)bis(4-hydroxybenzamide) (diol 4) was recounted. The diol 4 was supplied by Vitas-M Laboratory, Ltd (Moscow, Russia). The key monomer applied in this project was diol 4. The direct polycondensation reaction of several chiral diacids (3A–3D) with aromatic diol 4 was carried out in a system of tosyl chloride, pyridine, and N,N-dimethyformamide. All the above PAEIs were characterized by proton nuclear magnetic resonance, Fourier transform infrared (FT-IR), elemental analysis, specific rotation techniques, x-ray diffraction, and field emission scanning electron microscopy (FE-SEM). Thermogravimetric analysis was used to study thermal properties of PAEIs. The FE-SEM of the aforementioned PAEIs indicated that these polymers were nanostructured particles. These polymers contain bioactive amino acids and diol units possibly with potential applications as biodegradable and biocompatible agents.
WathierMJohnsonCSKimT. Hydrogels formed by multiple peptide ligation reactions to fasten corneal transplants. Bioconjugate Chem2006; 17: 873–876.
2.
MasseyKABlakesleeCHPitkowHS.A review of physiological and metabolic effects of essential amino acids. Amino Acids1998; 14: 271–300.
3.
SandaFEndoT. Syntheses and functions of polymers based on amino acids. Macromol Chem Phys1999; 200: 2651–2661.
4.
GiganteAChillemiCBevilacquaC. Effect of elastin-derived peptide on Achilles tendon healing: an experimental study. J Mater Sci Mater Med2003; 14: 717–720.
5.
Pilkington-MiksaMAWriterMJSarkarS. Targeting lipopolyplexes using bifunctional peptides incorporating hydrophobic spacer amino acids: synthesis, transfection, and biophysical studies. Bioconjugate Chem2007; 18(6): 1800–1810.
6.
BrownMDGrayAITetleyL. In vitro and in vivo gene transfer with poly(amino acid) vesicles. J Control Release2003; 93: 193–211.
7.
GhoshMKMittalKL.Polyimides: fundamentals and applicators. New York, NY: Marcel &Dekker, 1996,pp. 146–154.
8.
NicolescuAFJercaVVAlbuAM. Synthesis and copolymerization study of new polyimide precursors with potential application in optical and photonic field. Mol Cryst Liq Cryst2008; 486: 38/[1080]–49/[1091].
9.
HasegawaMHorieK.Photophysics, photochemistry, and optical properties of polyimides. Prog Polym Sci2001; 26: 259–335.
10.
ArovaNAArtyukhovAIBaklaginaYG. Structure and properties of some crystallizable polyester imides (PEI). Vysokomol soyed1973; A15(1): 153–161.
11.
KimJWRyuSCVuQH. Synthesis and performance of polyimide films for the flexible organic light emitting diodes. Mol Cryst Liq Cryst2009; 513: 214–226.
12.
KoytepeSSeckinTKıvrılcımN. Synthesis and dielectric properties of polyimide-titania hybrid composites. J Inorg Organomet Polym2008; 18: 222–228.
13.
WangKLLiouWTLiawDJ. High glass transition and thermal stability of new pyridine-containing polyimides: effect of protonation on fluorescence. Polymer2008; 49:1538–1546.
14.
HuangCCJangGWChangKC. High-performance polyimide–clay nanocomposite materials based on a dual intercalating agent system. Polym Int2008; 57:605–611.
15.
YangCPSuYYWuKL.Synthesis and properties of new aromatic polyimides based on 2,5-bis(4-amino-2-trifluoromethylphenoxy)-tert-butylbenzene and various aromatic dianhydrides. J Polym Sci A Polym Chem2004; 42: 5424–5438.
16.
ShaoYLiYZhaoX. Synthesis and characterization of soluble polyimides derived from a novel unsymmetrical diamine monomer: 1,4-(2′,4′-diaminodiphenoxy)benzene. Eur Polym J2007; 43: 4389–4397.
17.
ChoiHChungISHongK. Soluble polyimides from unsymmetrical diamine containing benzimidazole ring and trifluoromethyl pendent group. Polymer2008; 49: 2644–2649.
18.
GhaemyMAlizadehR. Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group. Eur Polym J2009; 45: 1681–1688.
19.
YangCPSuYY.Colorless and high organosoluble polyimides from 2,5-bis(3,4-dicarboxyphenoxy)-t-butylbenzene dianhydride and aromatic bis(ether amine)s bearing pendent trifluoromethyl groups. Polymer2005; 46: 5778–5788.
20.
DaviesMHayJNWoodfineB.Polyetherimides-synthesis and structure-property relationships. High Perform Polym1993; 5: 37–45.
21.
KlausWLienertKW.Poly(ester-imide)s for industrial use. Adv Polym Sci1999; 141: 45–82.
NakanoT.Optically active synthetic polymers as chiral stationary phases in HPLC. J Chromatogr A2001; 906: 205–225.
24.
OkamotoY. Chiral polymers for resolution of enantiomers. J Polym Sci A Polym Chem2009; 47: 1731–1739.
25.
TakataTFurushoYMurakawaKI. Optically active poly(aryl carbonate)s consisting of axially chiral units-chiral binaphthyl group-induced helical polymer. J Am Chem Soc1998; 120: 4530–4531.
26.
Abdul RahimESandaFMasudaT.Synthesis and properties of optically active amino acid based polyacetylenes bearing eugenol and fluorene moieties. J Polym Sci A Polym Chem2006; 44: 810–819.
27.
ChenZTakeiYDeoreBA. Enantioselective uptake of amino acid with overoxidized polypyrrole colloid templated with l-lactate. Analyst2000; 125: 2249–2254.
28.
KozlovskyMV.Chiral polymers with photoaffected phase behaviour for photo-optical and optoelectronic applications. Synth Met2002; 127: 67–70.
29.
ItsunoS.Chiral polymer synthesis by means of repeated asymmetric reaction. Prog Polym Sci2005; 30: 540–558.
30.
KoyamaESandaFEndoT.Polycondensations of hydroxycarboxylic acids derived from optically active aminoalcohols and acid anhydrides-syntheses of functional poly(ester-amide)s. J Polym Sci A Polym Chem1997; 35:345–352.
31.
MallakpourSZadehnazariA. Synthesis of optically active and thermally stable polyamides with bulky aromatic side chain in an ionic liquid (tetrabutylammonium bromide). High Perform Polym2010; 22(5): 567–580.
32.
MallakpourSDinariM. A green route for synthesis of different polyureas based on phenylurazole: rapid solid-state, microwave-assisted technique. High Perform Polym2010; 22(3): 314–327.
33.
MallakpourSAsadiP. Novel chiral poly(ester-imide)s with different natural amino acids in the main chain as well as in the side chain: synthesis and characterization. Colloid Polym Sci2010; 288: 1341–1349.
34.
MallakpourSShahmohammadiMH. Synthesis of new optically active poly(amide-imide)s derived from N, N′-(pyromellitoyl)-bis-S-valine diacid chloride and aromatic diamines under microwave irradiation and classical heating. Iranian Polym J2005; 14: 473–483.
35.
MallakpourSHajipourARHabibiS. Facile synthesis of new optically active poly(amide-imide)s derived from N, N′-(pyromellitoyl)-bis-l-leucine diacid chloride and aromatic diamines under microwave irradiation. Eur Polym J2001; 37: 2435–2442.
36.
MallakpourSRafieeZApplication of microwave-assisted reactions in step-growth polymerization: a review. Iran Polym J2008; 17: 907–935.
37.
MallakpourSShahmohammadiMH. Microwave-promoted rapid synthesis of new optically active poly(amide-imide)s derived from N, N′-(pyromellitoyl)-bis-l-isoleucine diacid chloride and aromatic diamines. J Appl Polym Sci2004; 92: 951–959.
38.
HigashiFTobeA. A new polycondensation involving dicarboxylic acids with differently activated carboxyl groups by TsCl/DMF/Py. Macromol Chem Phys2001; 202: 745–749.
39.
HigashiFTakashiIAkyamaN. Further study of the direct polycondensation reaction of hydroxybenzoic acids with tosyl chloride and N, N-dimethylformamide. J Polym Sci Polym Chem Ed1984; 22: 3607–3610.
40.
NiHKawaguchiH.Mechanism of preparing monodispersed poly(acrylamide/methacrylic acid) microspheres in ethanol. II. J Polym Sci A Polym Chem2004; 42: 2833–2844.
41.
LinCZangZZhengJ. Crosslinked polyacrolein microspheres with high loading of aldehyde groups for use as scavenger resins in organic synthesis. Macromol Rapid Commun2004; 25: 1719–1723.
42.
Van KrevelenDWHoftyzerPJ. Properties of polymers. 3rd ed. Amsterdam, Netherlands: Elsevier, 1976.
