Highly diastereoselective synthesis of novel polymers via tandem Diels-Alder-ene reactions

Mallakpour, Shadpour; Hajipour, Abdol R.; Mahdavian, Ali Reza; Rafiemanzelat, Fatemeh

doi:10.1002/(sici)1097-0126(199902)48:2<109::aid-pi103>3.0.co;2-n

Cited by 43 publications

(28 citation statements)

References 25 publications

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“…Fluorescence spectra of polymer(10) in DMF, ex ϭ 283.2 nm at RT. 1 at C ϭ 9.1 ϫ 10 Ϫ8 M and 2 at C ϭ 9.1 ϫ 10 Ϫ9 M.…”

supporting

confidence: 89%

“…Thermal gravimetric analysis (TGA) of polymers (9) and (10) show that they are moderately thermally stable. For polymer (9), the TGA thermogram (Fig.…”

Section: Thermal Propertiesmentioning

confidence: 99%

“…The peak temperature during this weight loss is at 608°C. For polymer (10), the TGA thermogram (Fig. 8) shows a 5% weight loss at 225°C and the residual weight percent at 500°C is 17.6%.…”

Section: Thermal Propertiesmentioning

confidence: 99%

“…According to the UV-vis spectra of polymers (9,10) in DMF, the max at 283.2 nm was chosen, in which the maximum absorption was observed. The solutions were excited at this wavelength that is in the region of excitation for the naphthalenic moiety.…”

Section: Fluorimetric Studiesmentioning

confidence: 99%

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Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

Mallakpour

Hajipour

Mahdavian

2000

J. Appl. Polym. Sci.

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1‐Naphthylacetic acid (1) was reacted with thionyl chloride and 1‐naphthyl‐ acetyl chloride (2) was obtained in a quantitative yield. The reaction of this acid chloride (2) with isoeugenol (3) was performed in chloroform and a novel isoeugenol ester derivative (4) as a monomer was obtained in a high yield. The compound (4) was characterized by 1H‐NMR, IR, mass, and elemental analyses and then was used for the preparation of a model compound (6) and polymerization reactions. 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione (PhTD) (5) was allowed to react with compound (4). The reaction is very fast and gives only one double adduct (6) via Diels–Alder and ene pathways in an excellent yield. The polymerization reactions of the novel monomer (4) with bistriazolinediones [bis‐(p‐3,5‐dioxo‐1,2,4‐triazolin‐4‐ylphenyl)methane (7) and 1,6‐bis‐(3,5‐dioxo‐1,2,4‐triazolin‐4‐yl)hexane] (8) were carried out in N,N‐dimethylacetamide (DMAc) at room temperature. The reactions are exothermic and fast and gave novel heterocyclic polyimides containing a naphthalenic pendant group (9) and (10) via repetitive Diels–Alder‐ene polyaddition reactions. Stereochemical analysis of the model compound and fluorimetric studies of the model compound as well as polymers were done conclusively. Excimer formation of the polymers and its effect on fluorescence emission were investigated and some structural characterization and physical properties of these novel heterocyclic polyimides are reported. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 527–536, 2000

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“…Fluorescence spectra of polymer(10) in DMF, ex ϭ 283.2 nm at RT. 1 at C ϭ 9.1 ϫ 10 Ϫ8 M and 2 at C ϭ 9.1 ϫ 10 Ϫ9 M.…”

supporting

confidence: 89%

“…Thermal gravimetric analysis (TGA) of polymers (9) and (10) show that they are moderately thermally stable. For polymer (9), the TGA thermogram (Fig.…”

Section: Thermal Propertiesmentioning

confidence: 99%

Section: Thermal Propertiesmentioning

confidence: 99%

Section: Fluorimetric Studiesmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

Mallakpour

Hajipour

Mahdavian

2000

J. Appl. Polym. Sci.

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“…37 On the other hand, synthesis and application of optically active polymers are the newly considered topics that have been given more attention recently. [42][43][44][45] In this article we report a facile method for rapid synthesis of aromatic optically active poly-(ester-imide)s by using a domestic microwave oven and comparing with conventional solution polymerization results. 38 -41 Recently, we have synthesized optically active polymers by different methods.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted polycondensation of 4,4?-(hexafluoroisopropylidene)-N,N?-bis(phthaloyl-L-leucine) diacid chloride with aromatic diols

Mallakpour

Hajipour

Khoee

2000

J. Appl. Polym. Sci.

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Synthesis and characterization of novel optically active poly(amide‐imide)s

1999

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4,4′‐(Hexafluoroisopropylidene)‐bis‐(phthalic anhydride) (1) was reacted with L‐leucine (2) in toluene solution at refluxing temperature in the presence of triethylamine and the resulting imide‐acid (4) was obtained in quantitative yield. The compound (4) was converted to the diacid chloride (5) by reaction with thionyl chloride. The polymerization reaction of the imide‐acid chloride (5) with 1,6‐hexamethylenediamine (6a), benzidine (6b), 4,4′‐diaminodiphenylmethane (6c), 1,5‐diaminoanthraquinone (6d), 4,4′‐sulfonyldianiline (6e), 3,3′‐diaminobenzophenone (6f), p‐phenylenediamine (6g) and 2,6‐diaminopyridine (6h) was carried out in chloroform/DMAc solution. The resulting poly(amide‐imide)s were obtained in high yield and are optically active and thermally stable. All of the above compounds were fully characterized by IR, elemental analyses and specific rotation. Some structural characterization and physical properties of those optically active poly(amide‐imide)s are reported. © 1999 Society of Chemical Industry

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Highly diastereoselective synthesis of novel polymers via tandem Diels-Alder-ene reactions

Cited by 43 publications

References 25 publications

Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

Microwave-assisted polycondensation of 4,4?-(hexafluoroisopropylidene)-N,N?-bis(phthaloyl-L-leucine) diacid chloride with aromatic diols

Synthesis and characterization of novel optically active poly(amide‐imide)s

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