Synthesis of a new pyridine-containing diamine and related polyimide

Zhao, Jiu Jiang; Gong, Chenliang; Zhang, Shu Jiang; Shao, Yu; Li, Yan Feng

doi:10.1016/j.cclet.2009.11.004

Cited by 20 publications

(8 citation statements)

References 6 publications

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“…It is obvious that the presence of flexible ether linkages and bulky pendent groups with alicyclic pyrrolidine as side groups in the main chains were all beneficial to disturb the packing of molecules and make the solvent molecule penetrate easily, and then promote the solubility of the polymer. Moreover, the incorporation of nitrogen atoms from pyridine and pyrrolidine rings can generate polarized bonds, which can improve the solubility of polyimides due to the intermolecular dipole-dipole interactions in polymer–solvent system [42]. In addition, the dissolution characteristics of polymers in low-boiling solvent was very convenient for processing and forming them into desired products by solution casting method at lower temperatures.…”

Section: Resultsmentioning

confidence: 99%

“…The advantages of pyridine ring in different heterocycles come from its molecular symmetry and aromatic high thermal stability [40]. In addition, the presence of nitrogen atoms in pyridine rings can generate polarized bonds, which increase the solubility of polymers due to the intermolecular dipole-dipole interactions in a polymer-solvent system [41,42,43]. For example, PIs derived from 2-(5-(3,5-diaminophenyl)-1,3,4-oxadiazole-2-yl)pyridine [44] and 1,3-bis(5-amino-2-pyridinoxy)benzene [45] have all have been demonstrated to own high solubility and thermal properties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

et al. 2017

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Abstract:A novel aromatic diamine monomer, 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine (PPAPP) containing pyridine rings, pyrrolidine groups, and ether linkages, was successfully synthesized using 4-hydroxyacetophenone and 1-chloro-4-nitrobenzene as starting materials by three-step reactions, and then used to synthesize a series of polyimides by polycondensation with various aromatic dianhydrides via a two-step method. The structure of PPAPP was characterized by NMR, FT-IR, and mass spectrometry analysis methods. These polymers showed good solubility in common organic solvents (e.g., NMP, DMF, DMSO, and DMAc) at room temperature or on heating. Moreover, they presented a high thermal stability with the glass transition temperature (T g s) exceeding 316 • C, as well as the temperature of 10% weight loss ranged from 552 to 580 • C with more than 67% residue at 800 • C under nitrogen. Furthermore, they also exhibited excellent hydrophobicity with a contact angle in the range of 85.6 • -97.7 • , and the results of Wide-Angle X-ray Diffraction (WAXD) indicated that all of the polymers revealed an amorphous structure.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

et al. 2017

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“…So far, the major structural modification method has been involved by the introduction of flexible linkages, such as -O-, −S-, −CH 2 -and -SO 2 - [6][7][8], bulky substituents [9][10][11][12], bulky pendant group [13][14][15], non-coplanar [16,17], unsymmetrical structure, such as ortho-or metalinked unit [18][19][20], and acyclic moieties into the polymer backbones [21][22][23]. The solubility and optical transparency of polyimides could be improved by introduction of flexible ether and acyclic linkages in the polymer backbone.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties

et al. 2015

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A series of novel organo-soluble and optical transparent polyimides were synthesized via conventional one-step polycondensation from a novel diamine, 3,3′-diterbutyl-4,4′-diaminodiphenyl-4″-morpholinophenylmethane (TAMPM) and various commercial aromatic dianhydrides. The structures of monomer and polymers were confirmed by FT-IR and NMR. The solubility, thermal stability, optical transparency, dielectric and hydrophobic properties of polyimides were investigated. The results showed polymers presented excellent solubility in common organic solvents, such as N,Ndimethylformamide (DMF), N,N-dimethyl acetamide (DMAc), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), chloroform (CHCl 3 ), tetrahydrofuran (THF) and dichloromethane (CH 2 Cl 2 ). The polymers exhibited prominent thermal stability and high optical transparency with the glass transition temperature (T g ) in the range of 311-355°C, and the cutoff wavelengths in the range of 287-344 nm. Furthermore, all of the polymers also presented low dielectric constants in the range of 2.85-3.16 at 1 MHz, and outstanding hydrophobic properties with the contact angle in the rang of 85.1-94.2 o .

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“…1 –3 In order to improve PIs’ processibility, bulky substituents, flexible alkyl side chains, unsymmetric, noncoplanar structures, alicyclic, and kinked and fluorinated structures have been introduced into the polymer backbone. 1 –9 In recent years, in order to maintain excellent thermal properties, the rigid-rod PIs with high organic solubility have attracted some research efforts. These efforts have been focused on designing and synthesizing new rigid diamines that resulted in soluble and processable PIs without deterioration of their positive properties.…”

Section: Introductionmentioning

confidence: 99%

“…These efforts have been focused on designing and synthesizing new rigid diamines that resulted in soluble and processable PIs without deterioration of their positive properties. 4 –9 Many articles have reported that the PIs prepared from pyridine-containing diamine and dianhydride monomers exhibited good thermostability and processability. 10 –16…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly(pyridine–imide)s with tert-butyl substituents

Xiao

et al. 2014

High Performance Polymers

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The aromatic diamine monomer containing a pyridine heterocyclic group and a tert-butyl substituent, 4-[(4′-tert-butyl)phenyl]-2,6-bis(4-aminophenyl)pyridine (BPAP), was successfully synthesized by a modified Chichibabin reaction of 4-nitro-acetophenone and 4-tert-butyl benzaldehyde, followed by a reduction of the resulting dinitro compound 4-[(4′-tert-butyl)phenyl]-2,6-bis(4-nitrophenyl)pyridine with palladium/carbon and hydrazine monohydrate, successively. A series of poly(pyridine–imide)s were prepared from the diamine BPAP with the alicyclic anhydride 1,2,3,4-cyclobutanetetracarboxylic dianhydride, aromatic anhydride pyromelitic dianhydride, 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, and 4,4′-oxydiphthalic anhydride in N,N-dimethylformamide (DMF) via the conventional two-step method and further chemical imidization to obtain poly(pyridine-imide) powders. Due to the introduction of tert-butyl group, the polyimides (PIs) derived from BPAP were amorphous and displayed good solubility in amine-type polar solvents, such as DMF, dimethyl sulfoxide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. Because of the presence of rigid triphenylpyridine units and bulky substituents, the final PIs held a good thermal stability with 10% weight loss temperatures above 504°C and left more than 55% residue even at 700°C under nitrogen atmosphere. The effect of tert-butyl substituents on the properties of the PIs was studied by comparing with 4-phenyl-2,6-bis(4-nitrophenyl)pyridine. These PIs exhibited some fluorescent properties because of the triphenylpyridine units, and the chemical structure of dianhydrides took an effect on the fluorescent property of these PIs.

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Synthesis of a new pyridine-containing diamine and related polyimide

Cited by 20 publications

References 6 publications

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

Synthesis and Characterization of Organosoluble, Thermal Stable and Hydrophobic Polyimides Derived from 4-(4-(1-pyrrolidinyl)phenyl)-2,6-bis(4-(4-aminophenoxy)phenyl)pyridine

Synthesis and characterization of novel highly soluble and optical transparent polyimides containing tert-butyl and morpholinyl moieties

Synthesis and characterization of poly(pyridine–imide)s with tert-butyl substituents

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