Novel Polyaromatic Quinone Imines. 2. Synthesis of Model Compounds and Stereoregular Poly(quinone imines) from Disubstituted Anthraquinones

Boone, Harold W.; Hall, H. K.

doi:10.1021/ma9602435

Cited by 18 publications

(4 citation statements)

References 21 publications

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“…36 Its 1 H NMR spectrum was complicated and asymmetrical in the aromatic region. These data are consistent with the hypothesis that both syn and anti configurations are present in solution, because the alkoxy substituents are far removed from the imine functionality.…”

Section: Alkoxy-substituted Anthraquinones Model Compounds and Their mentioning

confidence: 99%

“…36 Because these compounds are symmetrically disubstituted with sterically bulky alkoxy-substituents, the central ring system is more buckled than for the parent DAQ (k max 398 nm), and therefore the extent of conjugation in the molecule is lower, resulting in lower k max values by a 22 nm shift.…”

Section: Alkoxy-substituted Anthraquinones Model Compounds and Their mentioning

confidence: 99%

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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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Section: Alkoxy-substituted Anthraquinones Model Compounds and Their mentioning

confidence: 99%

Section: Alkoxy-substituted Anthraquinones Model Compounds and Their mentioning

confidence: 99%

Condensation routes to polyaniline and its analogs

Hall

Padías

Boone

2007

J. Polym. Sci. A Polym. Chem.

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“…Aldimines and their metal complexes are well-known to undergo hydrolysis . However, ketimines and their hydrolytic cleavage phenomena are less explored, although there is a growing number of ketimine derivatives as chemosensors, macrocycles, polymers, and fluorescent dyes …”

Section: Introductionmentioning

confidence: 99%

Differential Sensing of Zn(II) and Cu(II) via Two Independent Mechanisms

Basa

Sykes

2012

J. Org. Chem.

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Selective reduction of an anthracenone-quinoline imine derivative, 2, using 1.0 equiv of NaBH(4) in 95% ethanol affords the corresponding anthracen-9-ol derivative, 3, as confirmed by (1)H NMR, (13)C NMR, ESI-MS, FTIR, and elemental analysis results. UV-vis and fluorescence data reveal dramatic spectroscopic changes in the presence of Zn(II) and Cu(II). Zinc(II) coordination induces a 1,5-prototropic shift resulting in anthracene fluorophore formation via an imine-enamine tautomerization pathway. Copper(II) induces a colorimetric change from pale yellow to orange-red and results in imine hydrolysis in the presence of water. Spectroscopic investigations of metal ion response, selectivity, stoichiometry, and competition studies all suggest the proposed mechanisms. ESI-MS analysis, FTIR, and single-crystal XRD further support the hydrolysis phenomenon. This is a rare case of a single sensor that can be used either as a chemosensor (reversibly in the case of Zn(II)) or as a chemodosimeter (irreversibly in the case of Cu(II)); however, the imine must contain a coordinating Lewis base, such as quinoline, to be active for Cu(II).

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“…The formation of the novel cyclic (α-phenyl)phenylazomethine trimer (CPA-a) was carried out by dehydration of 4-aminobenzophenone using TiCl 4 (Scheme , run 1) …”

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confidence: 99%