The coordination chemistry of substituted anthraquinones: Developments and applications

Langdon-Jones, Emily E.; Pope, Simon J. A.

doi:10.1016/j.ccr.2014.02.003

Cited by 63 publications

(48 citation statements)

References 132 publications

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“…A strong absorption band is observed between 350 and 400 nm and is assigned to π → π* transitions of carbonyl groups in the anthraquinone core [19,20]. These transitions, which usually occur below 350 nm in the base anthraquinone, are shifted to longer wavelengths in these colorants when electron donor groups, such as hydroxyls, are attached to the anthraquinone aromatic rings [20,21], as in the case of most organic red dyes. A minor shoulder between 470 and 500 nm is also sometimes visible.…”

Section: Introductionmentioning

confidence: 99%

Seeing red: towards an improved protocol for the identification of madder- and cochineal-based pigments by fiber optics reflectance spectroscopy (FORS)

et al. 2019

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Fiber optics reflectance spectroscopy (FORS) is commonly used to non-invasively identify madder-and cochinealbased pigments on works of art, but the significant shifts sometimes observed in the position of their diagnostic absorption features can hinder correct interpretation of the spectra. To better understand these shifts, and improve the ability to confidently identify these pigments, a systematic study was carried out to evaluate the effects of different pigment recipes and laking substrates on reflectance spectra. Sixteen different madder-and cochineal-based pigments were synthesized using historical recipes. Each pigment, painted in four different binding media (gum Arabic, linseed oil, beeswax, and egg yolk), was fully characterized by FTIR and HPLC-DAD-MS prior to FORS measurements. The results of the study showed that, in contrast to the absorption features typically used for identification, features in the first derivative transformation of the FORS spectra provided a more robust means of primary identification. In addition, once it has been identified as cochineal, the absorption features in the spectra of cochineal-based pigments could be correlated to the recipe employed, providing a possible means for inferring the method of manufacture and laking substrate from a non-invasive analysis. The results of this study were used to create a decision tree for the identification of madder and cochineal pigments based solely on FORS.

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Section: Introductionmentioning

confidence: 99%

Seeing red: towards an improved protocol for the identification of madder- and cochineal-based pigments by fiber optics reflectance spectroscopy (FORS)

et al. 2019

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“…6 Molecular sensors based on luminescent and colorimetric detection are more attractive due to their simplicity and low detection limits even at the nanomolar level. 20 Anthraquinone derivatives have been exploited as an efficient colorimetric chemosensors for the detection of metal ions and anions due to their very high absorption coefficient. The mechanisms described in the literature for the luminescence changes when detecting metal ions, anions or small molecules are mainly based on internal charge transfer (ICT) 7 , twisted internal charge transfer (TICT) 8 formation and the inversion of excited states (n-π* and π-π*).…”

Section: Introductionmentioning

confidence: 99%

Improved selectivity for Pb(ii) by sulfur, selenium and tellurium analogues of 1,8-anthraquinone-18-crown-5: synthesis, spectroscopy, X-ray crystallography and computational studies

et al. 2015

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We report here a series of heteroatom-substituted macrocycles containing an anthraquinone moiety as a fluorescent signaling unit and a cyclic polyheteroether chain as the receptor. Sulfur, selenium, and tellurium derivatives of 1,8-anthraquinone-18-crown-5 (1) were synthesized by reacting sodium sulfide (Na2S), sodium selenide (Na2Se) and sodium telluride (Na2Te) with 1,8-bis(2-bromoethylethyleneoxy)anthracene-9,10-dione in a 1 : 1 ratio. The optical properties of the new compounds are examined and the sulfur and selenium analogues produce an intense green emission enhancement upon association with Pb(II) in acetonitrile. Selectivity for Pb(II) is markedly improved as compared to the oxygen analogue 1 which was also competitive for Ca(II) ion. UV-Visible and luminescence titrations reveal that 2 and 3 form 1 : 1 complexes with Pb(II), confirmed by single-crystal X-ray studies where Pb(II) is complexed within the macrocycle through coordinate covalent bonds to neighboring carbonyl, ether and heteroether donor atoms. Cyclic voltammetry of 2-8 showed classical, irreversible oxidation potentials for sulfur, selenium and tellurium heteroethers in addition to two one-electron reductions for the anthraquinone carbonyl groups. DFT calculations were also conducted on 1, 2, 3, 6, 6 + Pb(II) and 6 + Mg(II) to determine the trend in energies of the HOMO and the LUMO levels along the series.

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“…[14] Moreover, in more recent applications anthraquinone group represents an important chemical component for the design of colorimetric sensors of anions/ cations or other chemical species. [5,[15][16][17][18][19][20][21][22] The color of AQ derivatives often show solvatochromic characteristics, [23,24] while it may be pH-sensitive. [25] Moreover, many derivatives (usually, hydroxyl-or amino-substituted anthraquinones) are fluorescent.…”

Section: Doi: 101002/mame201700450mentioning

confidence: 99%

“…Anthraquinone (AQ) derivatives, mostly based on 9,10-anthraquinone, represent a large group of organic chromophores with a wide variety of applications, for example dyes and pigments, or biological and medicinal products. [1][2][3][4][5] In fact, several AQ species (like hydroxy-anthraquinone) are naturally occurring products, [1,[6][7][8][9][10] often proposed for biological/medicinal applications. Moreover, the catalyzed oxidation/reduction of AQ derivatives has been widely applied for the alkaline delignification of wood, [11] while AQ or more elaborated derivatives [12] are used or proposed for the production of hydrogen peroxide (anthraquinone process).…”

Section: Introductionmentioning

confidence: 99%

UV‐Triggered Optical Response and Oxygen Scavenging Ability of a Water‐Soluble Poly(N,N‐dimethylacrylamide‐co‐2‐vinylbenzylanthraquinone) Copolymer

Karamitrou

Voyiatzis

Kallitsis

et al. 2017

Macro Materials & Eng

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A vinyl‐modified anthraquinone (AQ) derivative (Vinyl‐AQ) is synthesized through a palladium‐mediated Suzuki coupling reaction between vinylphenylboronic acid and 2‐chloromethylanthraquinone and, subsequently, copolymerized with N,N‐dimethylacrylamide (DMAM) through free radical copolymerization in organic solvent. The chemical structure of the resulting water‐soluble copolymer, P(DMAM‐co‐AQ), is verified using techniques such as proton nuclear magnetic resonance, attenuated total reflection‐infrared spectroscopy, thermogravimetric analysis, and UV–vis spectroscopy. The evolution of the oxygen scavenging abilities of aqueous P(DMAM‐co‐AQ) solutions after UV irradiation is monitored as a function of UV irradiation time, concentration of AQ moieties, and pH. The copolymer is proved an effective UV‐triggered oxygen scavenger, leading to dissolved oxygen contents below 1 ppm for the optimized experimental conditions. This behavior is related with the appearance of novel chemical species with interesting optical properties, as suggested by the respective evolution of the UV–vis absorption and photoluminescence spectra after UV irradiation.

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The coordination chemistry of substituted anthraquinones: Developments and applications

Cited by 63 publications

References 132 publications

Seeing red: towards an improved protocol for the identification of madder- and cochineal-based pigments by fiber optics reflectance spectroscopy (FORS)

Seeing red: towards an improved protocol for the identification of madder- and cochineal-based pigments by fiber optics reflectance spectroscopy (FORS)

Improved selectivity for Pb(ii) by sulfur, selenium and tellurium analogues of 1,8-anthraquinone-18-crown-5: synthesis, spectroscopy, X-ray crystallography and computational studies

UV‐Triggered Optical Response and Oxygen Scavenging Ability of a Water‐Soluble Poly(N,N‐dimethylacrylamide‐co‐2‐vinylbenzylanthraquinone) Copolymer

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