Synthesis and characterization of processable aromatic poly(azomethine)s with ether linkages

Yeakel, C; Gower, Karmen; Mani, R. S.

doi:10.1002/macp.1993.021941012

Cited by 24 publications

(6 citation statements)

References 16 publications

(1 reference statement)

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“…Aromatic poly(azomethine)s belong to a class of high performance materials that are known because of their excellent thermal stability, good mechanical properties and environmental resistance, [1][2][3][4] but more particularly as promising materials with optoelectrical, photonic and magnetic application. [5][6][7][8] Numerous types of aromatic poly(azomethine)s have been synthesized by the condensation between aromatic dialdehydes and diamines.…”

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confidence: 99%

Self-Assembling Polycondensation of 4-Aminobenzaldehyde. Preparation of Star-Like Aggregates of Cone-Shaped Poly(azomethine) Crystals

Kimura

Zhuang

Kida

et al. 2003

Polym J

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KEY WORDSSelf-Assembling / Polycondensation / Poly(azomethine) / Crystallization / Morphology / Aromatic poly(azomethine)s belong to a class of high performance materials that are known because of their excellent thermal stability, good mechanical properties and environmental resistance, 1-4 but more particularly as promising materials with optoelectrical, photonic and magnetic application. [5][6][7][8] Numerous types of aromatic poly(azomethine)s have been synthesized by the condensation between aromatic dialdehydes and diamines. However, their high melting points and low solubility usually make them inaccessible for processing by conventional techniques. In order to improve their intractability, several approaches such as the introduction into the main chain of flexible aliphatic segments, bulky lateral substituents or fluorine groups have been attempted so far. [9][10][11][12] We have been studying on the morphology control of intractable polymers during solution polymerization, and succeeded in preparing the whiskers of poly(poxybenzoyl) and other aromatic polyesters by polymerization in liquid paraffin (LPF). [13][14][15][16][17][18] These whiskers are formed by the reaction-induced crystallization of oligomers during solution polymerization. The polymer chains are aligned along the long axis of the whiskers and they show single crystal nature. This morphology and the chain alignment are desirable to endow the essential properties for industrial materials such as organic reinforcements. The formation mechanism of these whiskers contains the following three steps: (1) When the degree of polymerization of the oligomers exceed a critical value, they are precipitated from the solution to form lamellae. (2) The lamellae pile up in the form of needle-like crystals with spiral growth.(3) Post-polymerization occurs topochemically in the needle-like crystals, and the whiskers consisting of high molecular weight extended polymer chains are eventually formed. 14 The preparation method of the whisker can be recognized as the self-assembling polycondensation accompanied by the reaction-induced crystallization of oligomers, and it is a very valuable method for the morphology control of intractable polymers to overcome the antagonistic problem between intractability and properties.In many reports it has been very difficult to obtain the high molecular weight poly(azomethine) (PAZM). One of reasons is that aromatic poly(azomethine)s are precipitated in the solution during polycondensation because of the low solubility. 12 Much effort was devoted recently to preparing soluble and fusible aromatic poly(azomethine)s in many different ways. [19][20][21] However, the modification of polymer chain structures sacrifices their essential properties derived from their straight rigid-rod structures. Precipitation during polymerization is of advantage to control the morphology by means of the reaction-induced crystallization of oligomers as described before. In this study, we report the morphology of PAZM crystals prepared by the self...

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confidence: 99%

Self-Assembling Polycondensation of 4-Aminobenzaldehyde. Preparation of Star-Like Aggregates of Cone-Shaped Poly(azomethine) Crystals

Kimura

Zhuang

Kida

et al. 2003

Polym J

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“…They used 1,4-and 1,3-dibenzoylbenzene for condensation with various diamines -aromatic and aliphatic. Another approach to the PKs synthesis was presented by Yeakel et al [10], who used the halo-displacement method in which N,N 4 -bis[2-(4-halophenyl)benzylidene]1,4-benzenediamine was reacted with different diphenols and the resulting polymers had ketimine and ether linkages in the main chains. Thermal stability of the PKs with naphthalene pendent groups was studied by Sek [11].…”

Section: Introductionmentioning

confidence: 99%

Polyketanils: Preparation of π-Conjugated Polymer Bases from p-dibenzoylbenzene with Various Diamines. Protonation with DL-Camphor-10-sulfonic Acid

Iwan

Kasperczyk

Kaczmarczyk

et al. 2007

High Performance Polymers

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New luminescent materials - aromatic polyketanils (PKs) containing p-phenylene and biphenylene linkages in the backbone and electron-donating side-group substitutions have been synthesized via melt polycondensation (180°C, 24 h). Their structures were confirmed by elemental and spectral Fourier transform infrared, 13Cand 1H NMR, and ultraviolet-visible (UV-vis) analysis. All the PKs were solution-processable and thermally stable, making them potential candidate materials for applications in microelectronics and aerospace. These ketanil polymers showed high thermal stability and well-defined glass transition temperatures ( Tg). The temperature at which the polymers lose 10% of their weight ( T10) ranged from 420 to 520°C. Depending on the polymer structure, PKs showed Tg values in the range of 133 to 244°C. Moreover, the polymers emit either blue radiation or green radiation depending on the mutual presence of conjugated and saturated chain segments. The HOMO/LUMO energy gap of the polymers was in the range of 2.74-2.19 eV. The photoluminescence properties of the PKs after protonation with DL-camphor-10-sulfonic acid (CSA) were tested. The structure formation of (PKs)1(CSA)2 complexes are discussed on the basis of 1HNMRspectroscopy.

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“…The polyketanils were investigated from the point of view of their thermal stability and conductivity before and after doping with iodine. Halodisplacement was used by Yeakel et al [17] and Matsuo et al [18] for the synthesis of polyketanils with ether linkages. Polyketanils with phenyl pendant groups were synthesized by Volpe et al [19][20][21] using p-and m-dibenzoylbenzene and diamines.…”

Section: Introductionmentioning

confidence: 99%

Molecular and supramolecular approaches for tuning properties of new polyketanils

Sęk

Iwan

2004

E-Polymers

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A new family of π-conjugated polyketanils was synthesized and thermal and optical properties of the polymers were tuned by 'chain engineering', consisting of the appropriate design of chain building blocks using diamines and diketones with various chemical structures, and 'dopant engineering' in which a specially designed multifunctional dopant was used, 1,2-(di-2-ethylhexyl) ester of 4-sulfophthalic acid, capable of specific interaction with the host polymer. The structure of the dopant creates a new type of supramolecular comb-shaped architecture in which the lateral groups, anions of the sulfophthalic acid residue, are ionically bonded to the main chain via protonation of ketimine nitrogen atoms. This specific interaction of the dopant with the host polymer influences the polyketanils' properties and the following changes were observed: decreasing glass transition temperature and improvement of polymer film flexibility, as well as a bathochromic shift of the photoluminescence emission band.

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Synthesis and characterization of processable aromatic poly(azomethine)s with ether linkages

Cited by 24 publications

References 16 publications

Self-Assembling Polycondensation of 4-Aminobenzaldehyde. Preparation of Star-Like Aggregates of Cone-Shaped Poly(azomethine) Crystals

Self-Assembling Polycondensation of 4-Aminobenzaldehyde. Preparation of Star-Like Aggregates of Cone-Shaped Poly(azomethine) Crystals

Polyketanils: Preparation of π-Conjugated Polymer Bases from p-dibenzoylbenzene with Various Diamines. Protonation with DL-Camphor-10-sulfonic Acid

Molecular and supramolecular approaches for tuning properties of new polyketanils

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