Synthesis and properties of semiconducting aromatic polyquinonediimines

Everaerts, Albert; Roberts, S.; Hall, H. K.

doi:10.1002/pola.1986.080240727

Cited by 16 publications

(23 citation statements)

References 4 publications

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“…1(b). This buckling angle is the same as that of the unsubstituted diimine 1c, 13 and is 8Њ larger than that of the 1,4-methoxy derivative 1d. 10 The peri-OH groups in 1a would have a role in retaining molecular planarity due to the intramolecular hydrogen bonds rather than exerting steric hindrance, leading to molecular buckling.…”

Section: Resultsmentioning

confidence: 72%

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Photocyclization of N,N ′-diphenyl-1-hydroxy-9,10-anthraquinone diimines via excited-state intramolecular proton transfer (ESIPT)

Kobayashi¹,

Iguchi²,

Imakubo³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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Section: Resultsmentioning

confidence: 72%

“…General methods 1 H and 13 C NMR spectra were recorded at 500 MHz in CDCl 3 unless specified otherwise and are reported in ppm units with TMS as internal standard. J values are given in Hz.…”

Section: Methodsmentioning

confidence: 99%

Photocyclization of N,N ′-diphenyl-1-hydroxy-9,10-anthraquinone diimines via excited-state intramolecular proton transfer (ESIPT)

Kobayashi¹,

Iguchi²,

Imakubo³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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“…The IR spectra were recorded on a IR-470 Shimadzu spectrophotometer using the KBr pellet technique. 1 H-NMR spec-tra were run on a Varian EM-390 90-MHz NMR spectrometer at room temperature in dimethylsulfoxide (DMSO) using tetramethylsilane as the internal reference. The UV-visible spectra were scanned on a Shimadzu 2110 PC scanning spectrophotometer in dimethylformamide (DMF).…”

Section: Experimental Measurementsmentioning

confidence: 99%

“…It is well known that electronic mobility in conjugated organic polymers is greatly enhanced along a polymer molecule with conjugated bonds, A great variety of such materials have received attention. [1][2][3][4][5] These materials are prepared by polymerization of simple monomers that are able to form a network of highly delocalized electrons. Moreover, conjugated organic polymers have gained increasing interest in recent years as electrically conducting polymers [e.g., poly(p-phenylene), polypyrrole, polythiophene, and others].…”

Section: Introductionmentioning

confidence: 99%

New polymer syntheses. V. Synthesis, characterization, and morphology of new conjugated polymers, copolymers, and terpolymers containing piperidone moiety in main chain

Aly

1999

J. Appl. Polym. Sci.

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ABSTRACT:A new interesting category of polyconjugated polymer, poly(3,5-benzylidene)isopropylpiperidone, was obtained by condensation of isopropylpiperidone with terephthalaldehyde. Copolymerization and terpolymerization with cyclopentanone and/or cyclohexanone were also carried out. The model compound was prepared by the condensation of 2 mol benzaldehyde with isopropylpiperidone; the structure was elucidated by IR, 1 H-NMR spectra, and elemental analyses. The polymers, copolymers, and terpolymers were characterized by elemental analyses, IR, 1 H-NMR spectra, UV and visible spectra, viscometry, and X-ray analysis. The thermal behavior of the synthesized polymers was evaluated by TGA and DSC analyses and correlated with their structures. The morphology of terpolymer IV was examined by a scanning electron microscope. Electrical conductivities in the 10 Ϫ9 -10 Ϫ11 ⍀ Ϫ1 cm Ϫ1 range were observed: doping with iodine showed a small increase.

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“…The diimine model compound DAQ was synthesized in crystalline form. 20 X-ray single crystal structure determination revealed that the centralfused ring system was not planar, but buckled 268 to a \butterfly" configuration. A similar butterfly configuration has been reported for N,N 0 -dicyanoanthraquinone-9,10-diimine, with the cyano groups in the syn configuration.…”

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confidence: 99%

Condensation routes to polyaniline and its analogs

Hall

Padías

Boone

2007

J. Polym. Sci. A Polym. Chem.

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To obtain polyanilines which are more structurally perfect than those obtainable by the oxidation of anilines, polycondensation procedures were investigated. Model reactions gave extensive information about yields and about the physical properties of the putative structural polymer units. Condensation of anthraquinones with aromatic diamines using titanium tetrachloride and the unique base, 1,4-diazabicyclo-[2.2.2]-octane Dabco, gave high molecular weight orange polyquinonimines. Alkoxy groups on the anthraquinone ring aided solubility and molecular weight, and appropriately positioned alkoxy groups afforded stereoregular polymers. A bisthiophene benzoquinone also polymerized successfully. Application of the same procedure to 2,5-dimethyl-p-benzoquinone gave stereoregular poly(arylene benzoquinonimines), close analogs of pernigrani line. The factors causing problems in achieving high yields and high molecular weight were identified. Recent synthetic developments in this field are discussed. Reduction of the obtained polyquinonimines proceeded smoothly to the leucoemeraldine analogs. Unlike the results from pernigraniline obtained by oxidative polymerization, no evidence for the formation of the electrically conductive emeraldine form was obtained. Keywords: conducting polymers; conjugated polymers; polyaniline; polycondensation; polyimines H. K. Hall, Jr., received his B.S. at Brooklyn Polytech, M.S. at Pennsylvania State University, and Ph.D. from the University of Illinois in 1949. Postdoctoral work followed, with Prof. P. J. Flory at Cornell and with Professors S. Winstein and W. G. Young at UCLA. After 17 years at DuPont, he moved in 1969 to the University of Arizona. His research interests have included the ring-opening polymerizations of strained bicyclic molecules, the mechanisms of reactions of donor with acceptor olefins, the polymerization of imines, and the synthesis of electrically conductive, piezoelectric, and nonlinear optical polymers.

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Synthesis and properties of semiconducting aromatic polyquinonediimines

Cited by 16 publications

References 4 publications

Photocyclization of N,N ′-diphenyl-1-hydroxy-9,10-anthraquinone diimines via excited-state intramolecular proton transfer (ESIPT)

Photocyclization of N,N ′-diphenyl-1-hydroxy-9,10-anthraquinone diimines via excited-state intramolecular proton transfer (ESIPT)

New polymer syntheses. V. Synthesis, characterization, and morphology of new conjugated polymers, copolymers, and terpolymers containing piperidone moiety in main chain

Condensation routes to polyaniline and its analogs

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