Novel para-linked and CF3-substituted poly(amide-ether-imidazole)s: Solubility, optical and thermal properties

Ghaemy, Mousa; Berenjestanaki, Farshad Rahimi

doi:10.1016/j.jfluchem.2012.07.014

Cited by 16 publications

(8 citation statements)

References 34 publications

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“…The synthetic procedures for the synthesis of target diamine, 2-(4-trifluoromethylphenyl)-4,5-bis(4-(4-amino-2-TFIA are reported in the previous paper [37].…”

Section: Monomer Synthesismentioning

confidence: 99%

“…In the present study, the fluorinated polyimides were prepared via two-step condensation using chemical imidization. A new aromatic diamine (TFIA) was synthesized according to the synthetic procedure reported in the previously published paper [37]. Three new polyimides containing imidazol-triflouromethyl pendent groups were prepared in good yields (90-95%) by polycondensation of equal molar amounts of the diamine with commercially available aromatic dianhydrides, such as PMDA, BTDA, and 6FDA as shown in Scheme 1.…”

Section: Pieis Synthesis and Characterizationmentioning

confidence: 99%

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Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Ghaemy

Berenjestanaki

Bazzar

2013

Designed Monomers and Polymers

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A photoactive highly fluorinated diamine was synthesized, characterized, and used in preparation of structurally confirmed poly(imidazole-ether-imide)s (PIEIs). These polymers showed excellent solubility, moderate viscosities, good thermal stability (T g = 230-280°C, T i = 390-435°C, T 10% = 480-510°C), low dielectric constant (2.60-2.76), and water absorptions. The PIEIs films showed highly optical transparency with light transmittance at 550 nm of as high as 80% and cutoff wavelength of as low as 390 nm. These polymers exhibited fluorescence emission peaks around 410-490 nm with the quantum yields measured in solution varied from 12 to 32%.

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“…The synthetic procedures for the synthesis of target diamine, 2-(4-trifluoromethylphenyl)-4,5-bis(4-(4-amino-2-TFIA are reported in the previous paper [37].…”

Section: Monomer Synthesismentioning

confidence: 99%

Section: Pieis Synthesis and Characterizationmentioning

confidence: 99%

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Ghaemy

Berenjestanaki

Bazzar

2013

Designed Monomers and Polymers

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“…Scheme 1 illustrates synthesis steps of the target diamine (IV). Compounds (I) and (II) were synthesized by condensation of benzil with 2-chloro-5-nitrobenzaldehyde and ammonium acetate which is well known as a classical but convenient synthetic method for preparation of triaryl imidazole [19,41]. The dinitro (III) was synthesized by nucleophilic aromatic substitution reaction of compound II with compound I in DMAc and in the presence of K 2 CO 3 .…”

Section: Synthesis and Characterization Of Monomer And Polymersmentioning

confidence: 99%

Synthesis, Characterization and Heavy Metal Ion Adsorption Behavior of Imidazole-Based Novel Polyamides and Polyimides

2017

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Imidazole-based polyamides (PA)s and polyimides (PI) s were prepared from condensation of a new aromatic heterocyclic diamine, 4,4›(4,4›-(2-(4-(triflouromethyl)phenyl)-1H-imidazole-4,5-dyl)bis(4,1-phenylen))bis(oxy)bis(3-(4,5-diphenyl-1H-imidazole-2-yl)aniline), with various diacids and dianhydrides, respectively. The structure of diamine, PAs and PIs were fully characterized by using elemental analysis, FT-IR, 1H NMR and 13C NMR techniques. Also, adsorption capability of these polymers for removal of heavy metal ions such as Co2+, Cr3+, Cd2+, Hg2+ and Pb2+ from aqueous solutions was also tested at pH 7-8. The PAs and PIs showed good solubility in aprotic polar organic solvents with high thermal stability exhibiting the glass transition temperatures (Tg)s and 10% weight loss temperatures (T10%) in the range of 220-286 °C and 383-435 °C for PAs and 251-307 °C and 407-512 °C for PIs.

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“…Among them, it was found that incorporation of the fluorine groups like trifluoromethyl (CF 3 ) groups into PA backbones resulted in great benefits for improving the polymers, some properties such as solubility and optical transparency, as well as reducing the moisture absorption, crystallinity, dielectric constant, and color. 13 –19 Furthermore, the introduction of bulky loops substituents (usually named as cardo groups) (e.g. cyclododecylidene, tert -butylcyclohexylidene, tricyclo[5.2.1.0 2,6 ]decane, norbornane, fluorene, and xanthene) along the polymer backbone has been shown to impart greater solubility as well as better mechanical and thermal properties to the resulting PAs.…”

Section: Introductionmentioning

confidence: 99%

High optical transparency, low dielectric constant, and light color of organosoluble polyamides based on 10,10-bis[4-(4- amino-3-trifluoromethylphenoxy)phenyl]- 9(10H)-anthrone

Zhong

Huang

Wei

et al. 2019

High Performance Polymers

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A new aromatic diamine, 10,10-bis[4-(4-amino-3-trifluoromethylphenoxy)phenyl]-9( 10H)-anthrone (BATFPA), has been synthesized from anthrone via three-step procedure. Low-temperature polycondensation of BATFPA with various aromatic dicarboxylic acid chlorides produced novel fluorinated polyamides with moderate to high inherent viscosities of 0.75–1.03 dL/g while the weight-average molecular weight and number-average molecular weight were in the range of 66,000–74,000 and 37,000–41,000, respectively. Nearly, all the polymers were readily soluble in polar solvents, such as N,N-dimethyl acetamide (DMAc), N-methyl-2-pyrrolidinone, pyridine, and tetrahydrofuran, and afforded transparent, light-colored, and flexible films upon casting from DMAc solvent. These polymers had glass transition temperatures of 249–309°C, 10% weight loss temperatures of 486–517°C, and char yields of 53–61% at 800°C under nitrogen. All polymers were amorphous and their films exhibited tensile strengths of 64–86 MPa, tensile moduli of 1.8–2.2 GPa, and elongation at break of 10–18%. These polymers had dielectric constants ranging from 3.25 to 3.76 (100 Hz), low moisture uptake in the range of 0.72–1.18%, and high transparency with an ultraviolet–visible absorption cutoff wavelength in the 360–378 nm range.

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Novel para-linked and CF3-substituted poly(amide-ether-imidazole)s: Solubility, optical and thermal properties

Cited by 16 publications

References 34 publications

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

Synthesis, Characterization and Heavy Metal Ion Adsorption Behavior of Imidazole-Based Novel Polyamides and Polyimides

High optical transparency, low dielectric constant, and light color of organosoluble polyamides based on 10,10-bis[4-(4- amino-3-trifluoromethylphenoxy)phenyl]- 9(10H)-anthrone

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