Synthesis and Electrochemical Complexation Studies of 1,8-Bis(azacrown ether)anthraquinones

Echegoyen, Luis; Lawson, Raphael C.; Lopez, C.; Mendoza, Javier de; Hafez, Y.; Torres, Tomás

doi:10.1021/jo00093a013

Cited by 14 publications

(7 citation statements)

References 2 publications

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“…Similar direct alkylations were conducted for the alkylated macrocycles L2 and L3 without success. With this in mind L2 and L3 were synthesized in a two building block approach (Scheme ) ,…”

Section: Resultsmentioning

confidence: 99%

“… Synthesis of L1 ‐ L3 . (a) Cs 2 CO 3 , DMF, 90 °C, 15 h (b) BH 3 ⋅THF, THF, 15 h, 70 °C (c) 33% HBr in acetic acid, phenol, 90 °C, 2 d (d) Na 2 CO 3 , MeCN, 85 °C, 2 d, (e) LiAlH 4 , THF, 70 °C, 2 d ,…”

Section: Resultsmentioning

confidence: 99%

“…Regarding the synthesis of L3 (Scheme ) a different protocol for the macrocyclization using anhydrous Na 2 CO 3 instead of Cs 2 CO 3 was used, as a consequence of the poor results achieved with the Cs salt ,,. Although the previously described synthesis of the dimesylated precursor was performed in situ , the compound was isolated before its use in the cyclization reaction with hexadecylamine, since in our experience the cyclization tends to work better with isolated and purified precursors. The cleavage of the tosyl groups in this case was performed with lithium aluminum hydride, since ether cleavage from macrocycles with a higher oxygen content under acidic conditions had been previously reported ,…”

Section: Resultsmentioning

confidence: 99%

“… Synthesis of L3 . (a) MsCl, pyridine, 30 min <0 °C, 2 h at 0 °C, (b) Na 2 CO 3 , MeCN 85 °C, 2 d, (c) LiAlH 4 , THF, 70 °C, 2 d ,…”

Section: Resultsmentioning

confidence: 99%

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Monoalkylated Cyclen Complexes for Efficient Proteolysis: Influence of Donor Atom Exchange

et al. 2018

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Metal complexes of cyclen have been widely used to hydrolytically cleave biomolecules (proteins, RNA, DNA) and model substrates. Such cleavage reactions, however, usually require a high pH, long incubation times and enhanced temperatures. The present study combines two straightforward approaches to increase the proteolytic cleavage activity of cyclen complexes: alkylation in order to improve interactions with hydrophobic domains of proteins as well as single and double heteroatom exchange in order to increase the Lewis acidity of the metal center, in this case Cu(II). This allows reactions with BSA and Mb as model proteins to be carried out also at nearphysiological conditions. A Cu(II) complex with an alkylated oxacyclen ligand was identified as the most efficient species. Furthermore, a dioxacyclen derivative was investigated in proteolytic reactions for the first time.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“… Synthesis of L3 . (a) MsCl, pyridine, 30 min <0 °C, 2 h at 0 °C, (b) Na 2 CO 3 , MeCN 85 °C, 2 d, (c) LiAlH 4 , THF, 70 °C, 2 d ,…”

Section: Resultsmentioning

confidence: 99%

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Monoalkylated Cyclen Complexes for Efficient Proteolysis: Influence of Donor Atom Exchange

et al. 2018

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“…Several dihydroxy-and dichloro-anthraquinones are commercially available and were a rich source of these novel AQ monomers. [33][34][35] As shown in Scheme 6, alkylation of the dihydroxyanthraquinones with alkyl iodides in the presence of KF/ Al 2 O 3 gave good yields of dialkoxyanthraquinones, while nucleophilic displacement of 1,5-dichloroanthraquinone by monoglyme ethers gave the dimeric, trimeric, and tetrameric ethyleneoxy derivatives. Condensation of 1,5-dimethoxyanthraquinone with aniline using the standard TiCl 4 /Dabco procedure led to N,N 0 -bisphenyl-1,5-dimethoxyanthraquinonediimine.…”

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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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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Supramolekulare Elektrochemie

1998

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Welche Möglichkeiten bietet die Elektrochemie der supramolekularen Chemie? Einerseits liefert sie Informationen, die mit spektroskopischen und massenspektrometrischen Methoden nicht zugänglich sind, andererseits lassen sich mit ihr supramolekulare Wechselwirkungen beeinflussen. Rechts ist exemplarisch das Cyclovoltammogramm des gezeigten Lanthan‐Kryptats abgebildet; nur die ersten drei Reduktionen werden registriert, obwohl insgesamt sechs Elektronen auf die Bipyridineinheiten übertragen werden können (E in V gegen Ferrocen/Ferrocenium).

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Synthesis and Electrochemical Complexation Studies of 1,8-Bis(azacrown ether)anthraquinones

Cited by 14 publications

References 2 publications

Monoalkylated Cyclen Complexes for Efficient Proteolysis: Influence of Donor Atom Exchange

Monoalkylated Cyclen Complexes for Efficient Proteolysis: Influence of Donor Atom Exchange

Condensation routes to polyaniline and its analogs

Supramolekulare Elektrochemie

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