Preparation of Aromatic Polyesters under Unstoichiometric Condition by Reaction-induced Crystallization of Oligomers. 1. Polymerization of <i>p</i>-Acetoxybenzoic Acid in the Presence of Alkyloxybenzoic Acid

Kimura, Kunio; Kohama, Shin Ichiro; Yamashita, Yuhiko

doi:10.1021/ma0205919

Cited by 24 publications

(17 citation statements)

References 21 publications

(38 reference statements)

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“…Recently, some examples for new kinds of topochemical and solid-state polymerizations have been reported. [153][154][155][156][157][158][159][160] Polymer syntheses in the solid state will become more important in the future.…”

Section: Resultsmentioning

confidence: 99%

Polymer Structure Control Based on Crystal Engineering for Materials Design

Matsumoto

2003

Polym J

111

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ABSTRACT:In this review article, polymer structure control and organic material design based on polymer crystal engineering are described. The structures and properties of crystalline materials are designed using pre-organized molecules through various intermolecular interactions such as hydrogen bonds, π · · · π, CH/π, CH/O, and halogen interactions. Here, we describe the features and mechanisms of the topochemical polymerization of 1,3-diene monomers including some ester, ammonium, and amide derivatives of muconic and sorbic acids, which are 1,3-diene di-and monocarboxylic acid derivatives, respectively. We have proposed the topochemical polymerization principles for diene monomers on the basis of the crystallographic data accumulated for various kinds of diene monomers. The combination of several intermolecular interactions is useful for the construction of molecular packing appropriate for 5 Å stacking in order to facilitate the topochemical polymerization in the crystalline state. We refer to the control of polymer chain structure including tacticity, molecular weight, and ladder structure, and also polymer crystal structures, as well as the organic intercalation system using layered polymer crystals obtained by the topochemical polymerization. A totally solvent-free system for the synthesis of layered polymer crystals is also described.KEY WORDS Topochemical Polymerization / Solid-State Reaction / Crystal Engineering / Supramolecular Synthon / Stereoregular Polymer / Controlled Radical Polymerization / X-Ray Single Crystal Structure Analysis / Intercalation / Controlled polymer synthesis, including the control of polymer chain structures such as molecular weight, molecular weight distribution, chain-end structure, branching, regioselectivity, and stereoselectivity, has great potential for the design of macromolecular architecture leading to advanced nano-materials and devices. [1][2][3][4][5][6][7][8][9][10][11] All the features and functions of polymers importantly depend on primary chain structures and the manner of polymer chain assembly in crystalline and non-crystalline solids, or in a condensed state. Therefore, the control of polymer chain structures in polymer synthesis can hardly be overestimated for the architecture of advanced polymeric materials.Especially, the stereochemistry of polymers has received significant attention in both fundamental and applied fields ever since the first discoveries of stereoregular polymers in the 1950s. 12-14 Highly controlled stereospecific polymerization has been well established by coordination polymerization of olefins and diene monomers and by anionic polymerization of certain types of polar monomers. Radical polymerization is the most important and convenient process for the production of various kinds of vinyl and diene polymers due to recent achievements in well-controlled polymerizations in addition to the classical advantages of the radical process. [15][16][17][18][19][20][21][22] There are two fundamentally different ways to control of the chain structu...

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Section: Resultsmentioning

confidence: 99%

Polymer Structure Control Based on Crystal Engineering for Materials Design

Matsumoto

2003

Polym J

111

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“…The DP n of the polymers is estimated with the eqn (1) on the basis of the molar ratio of the two reactive groups corrected for the difference in the reactivity of acetoxy group to carboxylic acid between monomers and monocarboxylic acids14, 27 where N 0 is number of ABPA or ANA molecules, N 1 is number of monocarboxylic acid molecules, p is extent of reaction and r is a reactivity ratio of monocarboxylic acid to ABPA or ANA.…”

Section: Resultsmentioning

confidence: 99%

“…The POBP obtained in TS8 at χ E ≥ 60 mol% did not exhibit clear crystal habit and this implies that crystallization did not occur favorably in these polymerizations. According to the polycondensation mechanism under nonstoichiometric conditions of POB,14 crystallization of oligomers is a very important way to increase molecular weight in solid‐state polymerization. The lack of crystallization results in low molecular weight POBP.…”

Section: Resultsmentioning

confidence: 99%

“…These direct polycondensations were carried out in homogeneous solutions, and the stoichiometries between the two functional groups in the polymerization system is of great importance in preparing high molecular weight polymers. We have been studying the nonstoichiometric polycondensation of aromatic polyesters by means of reaction‐induced crystallization of oligomers during solution polymerization and successfully prepared high molecular weight poly( p ‐oxybenzoyl) (POB) crystals from 4‐acetoxybenzoic acid under nonstoichiometric conditions with 4‐alkyloxybenzoic acid in liquid paraffin (LPF) at 320 °C 14. The polycondensation proceeds under nonstoichiometric conditions through the following mechanisms.…”

Section: Introductionmentioning

confidence: 99%

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Direct synthesis of poly(4′‐oxy‐4‐biphenylcarbonyl) and poly(2‐oxy‐6‐naphthoyl) under nonstoichiometric conditions

Kohama

Kimura

Uchida

et al. 2004

Polymer International

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Direct synthesis of poly(4 -oxy-4-biphenylcarbonyl) (POBP) and poly(2-oxy-6-naphthoyl) (PON) was examined by polycondensation of 4 -hydroxy-4-biphenylcarboxylic acid (HBPA) and 2hydroxy-6-naphthoic acid (HNA) in the presence of 4-ethoxybenzoic anhydride or 2-naphthoic anhydride as condensation reagents. Polymerizations were carried out at 320 • C in aromatic solvents and liquid paraffin. POBP, having a number-average degree of polymerization (DPn) of 38, was obtained as platelike crystals at the molar ratio of HBPA and anhydride of 50 mol%. PON was also obtained as plate-like crystals but the DPn was only 13. HBPA and HNA were first converted to reactive acyloxyaromatic acid intermediates. Then the DPn was increased by means of reaction-induced crystallization of oligomers and subsequent solid-state polymerization via an acid-ester exchange under nonstoichiometric conditions caused by the monocarboxylic acid by-product. Even though the DPn of PON was not as high, direct polycondensation of HBPA and HNA proceeded successfully with aromatic anhydrides.

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“…125,126 It is also easy to prepare the aldehydes used in the syntheses of HL57-HL60 (Chart 6) by reported methods. [127][128][129] Selenoether ligands can be easily prepared by selenylation of an appropriate organic halocompound with suitable diaryldiselenide or dialkyldiselenide under reductive conditions, e.g. L61 58 and L62.…”

Section: Dalton Transactionsmentioning

confidence: 99%

Organosulphur and related ligands in Suzuki–Miyaura C–C coupling

et al. 2013

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Suzuki-Miyaura C-C cross coupling (SMC), an important synthetic strategy for many organic molecules, has several advantages such as mild reaction conditions, high tolerance toward various functional groups and ease in isolation of the product. Palladium(II) ligated with phosphines (particularly bulky and electron-rich) and N-heterocyclic carbenes (NHCs) has been found to be efficient in the catalysis of SMC. The drawback with many of these catalysts is their air/moisture sensitivity. Since 2000, palladium(II) complexes of organosulphur and related ligands have emerged as viable alternatives to palladium-phosphine/carbene complexes as they have sufficient thermal stability, air and moisture insensitivity. Moreover synthesis of complexes of such ligands is easy. In this perspective Suzuki-Miyaura C-C coupling reactions catalyzed with palladium(II)-complexes of organosulphur ligands have been reviewed. Catalysis of SMC with palladium(II) complexes of organoselenium and tellurium ligands, studied much less in comparison to those of organosulphur ligands, is also included.

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Preparation of Aromatic Polyesters under Unstoichiometric Condition by Reaction-induced Crystallization of Oligomers. 1. Polymerization of p-Acetoxybenzoic Acid in the Presence of Alkyloxybenzoic Acid

Cited by 24 publications

References 21 publications

Polymer Structure Control Based on Crystal Engineering for Materials Design

Polymer Structure Control Based on Crystal Engineering for Materials Design

Direct synthesis of poly(4′‐oxy‐4‐biphenylcarbonyl) and poly(2‐oxy‐6‐naphthoyl) under nonstoichiometric conditions

Organosulphur and related ligands in Suzuki–Miyaura C–C coupling

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