Synthesis, isolation, characterization, and properties of small-size aromatic macrocycles for poly(arylene ether ketone)s

Wang, Junzuo; Chen, Chunhai; Xun, X.; Wang, Shiying; Wang, Zhongwen

doi:10.1002/(sici)1099-0518(19990701)37:13<1957::aid-pola9>3.0.co;2-k

Cited by 14 publications

References 29 publications

(11 reference statements)

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Absolute Configuration Determination of a New Chiral Rigid Bisetherketone Macrocycle Containing Binaphthyl and Thioether Moieties by Vibrational Circular Dichroism

Cao¹,

Ben²,

Su³

et al. 2005

Macro Chemistry & Physics

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Summary: A new chiral rigid bisetherketone macrocycle containing binaphthyl and thioether moieties was synthesized successfully using a modified pseudo‐high dilution technique. The compound was characterized by means of infrared absorption (IR) and vibrational circular dichroism (VCD). The experimental IR and VCD spectra were compared with those computed based on density functional theory (DFT) calculations at B3LYP/6‐31G (d) level. Good agreement was observed between the experimental and calculated spectra and, therefore, the absolute configuration was determined. Knowledge of the absolute configuration is of great importance when exploring the mechanisms of chiral recognition based on the chiral macrocyclic molecules.Structure of the new chiral rigid bisetherketone macrocycle produced.imageStructure of the new chiral rigid bisetherketone macrocycle produced.

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Absolute Configuration Determination of a New Chiral Rigid Bisetherketone Macrocycle Containing Binaphthyl and Thioether Moieties by Vibrational Circular Dichroism

Cao¹,

Ben²,

Su³

et al. 2005

Macro Chemistry & Physics

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Fabrication of Aromatic‐Aliphatic Aminoketone Polymers with Terminal Fluorine Groups

Anders

Schrepp

Kaßner

et al. 2010

Macro Chemistry & Physics

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A procedure for synthesis aromatic‐aliphatic PAK, completely functionalized with p‐fluorophenyl terminal groups, is presented. This synthesis uses the nucleophilic aromatic substitution of DFB with various secondary aliphatic diamines [CH3NH(CH2)mNHCH3] (m = 3, 6, and 8) and cesium fluoride as the base catalyst in the melt. The linearity and the complete functionalization of the PAK compounds with p‐fluorophenyl terminal groups are demonstrated with the aid of MALDI TOF mass spectrometry. PAK compounds are semi‐crystalline as shown by WAXS and DSC measurements. The degree of crystallinity ranges between 2 and 25%. Nucleophilic aromatic substitution reactions in the fluorine end groups are demonstrated by reaction of PAK (m = 6) with the strong S‐nucleophile mercaptoacetic acid.magnified image

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Spontaneous Ring‐Opening Polymerization of Macrocyclic Aromatic Thioether Ketones under Transient High‐Temperature Conditions

Colquhoun

Zolotukhin

Zhu

et al. 2004

Macromol. Rapid Commun.

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Summary: Spontaneous ring‐opening polymerization of macrocyclic aromatic thioether ketones [1,4‐SC6H4COC6H4]n (n = 3 and 4), in which the thioether linkages are para to the ketone, occurs during rapid, transient heating to 480 °C, to afford a soluble, semi‐crystalline poly(thioether ketone) of high molar mass (ηinh > 1.0 dL · g−1). Corresponding macrocyclic ether ketones, and a macrocyclic thioether ether ketone in which the thioether linkage is para to the ether rather than to the ketone, show no evidence of polymerization under analogous conditions.The uncatalysed ring‐opening polymerization of macrocycle 1, within the pores of an alumina microfiltration membrane, leads to formation of polymer 3 with the microstructure shown in the above scanning electron micrograph.magnified imageThe uncatalysed ring‐opening polymerization of macrocycle 1, within the pores of an alumina microfiltration membrane, leads to formation of polymer 3 with the microstructure shown in the above scanning electron micrograph.

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Synthesis, isolation, characterization, and properties of small-size aromatic macrocycles for poly(arylene ether ketone)s

Cited by 14 publications

References 29 publications

Absolute Configuration Determination of a New Chiral Rigid Bisetherketone Macrocycle Containing Binaphthyl and Thioether Moieties by Vibrational Circular Dichroism

Absolute Configuration Determination of a New Chiral Rigid Bisetherketone Macrocycle Containing Binaphthyl and Thioether Moieties by Vibrational Circular Dichroism

Fabrication of Aromatic‐Aliphatic Aminoketone Polymers with Terminal Fluorine Groups

Spontaneous Ring‐Opening Polymerization of Macrocyclic Aromatic Thioether Ketones under Transient High‐Temperature Conditions

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