Absorption and emission spectroscopy and photochemistry of 1,10-anthraquinone derivatives: a review

Dı́az, A. Navas

doi:10.1016/1010-6030(90)87120-z

Cited by 147 publications

(29 citation statements)

References 87 publications

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“…[24,26] The low fluorescence of anthraquinone derivatives has been attributed to fast internal conversion due to intra-and intermolecular hydrogen bonds, as well as to intersystem crossingt ot he triplet excited state. [24,26] The low fluorescence of anthraquinone derivatives has been attributed to fast internal conversion due to intra-and intermolecular hydrogen bonds, as well as to intersystem crossingt ot he triplet excited state.…”

Section: Resultsmentioning

confidence: 99%

A Metal‐Free, Nonconjugated Polymer for Solar Photocatalysis

Irigoyen-Campuzano

González‐Béjar

Pino

et al. 2017

Chemistry A European J

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Heterogeneous catalysts that can absorb light over the solar range are ideal for green photocatalysis. Recently, attention has been directed towards the generation of novel solar-light photocatalysts, in particular, metal-free polymers. Herein, it is demonstrated that a metal-free, nonconjugated, anthraquinone-based copolymer (poly[1,4-diamine-9,10-dioxoanthracene-alt-(benzene-1,4-dioic acid)] (COP)) with a strong absorption in the visible region is effective as a sunlight heterogeneous photocatalyst. As a proof of concept, it has been used to mineralize 2,5-dichlorophenol (2,5-DCP) in water under air and sunlight irradiation. The photocatalytic efficiency of COP compares well with that of TiO -P25 when the reaction is carried out in a solar photoreactor in acid medium. Steady-state and time-resolved (absorption and emission) studies performed on COP suspended in 6:4 DMF/H O have provided valuable information about the COP species generated under different pH conditions. Steady-state absorption and fluorescence data are consistent with the existence of a tautomeric equilibrium between the 9,10-keto and 1,10-iminoketo quinoid forms for the anthraquinone in the ground state. Moreover, in basic media, transient absorption measurements showed the presence of two bands ascribed to the tautomeric triplet excited states, whereas only one of the triplets was observed in acid medium. A mechanism for the photocatalyzed degradation of 2,5-DCP by COP is proposed on the basis of these observations.

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Section: Resultsmentioning

confidence: 99%

A Metal‐Free, Nonconjugated Polymer for Solar Photocatalysis

Irigoyen-Campuzano

González‐Béjar

Pino

et al. 2017

Chemistry A European J

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“…, due to S π→π* electronic transitions) and one n → π* absorption band at longer wavelengths, close to 400 nm ( i.e. , due to S n→π* electronic transitions) (Diaz 1990). …”

Section: Introductionmentioning

confidence: 99%

“…The UV/vis spectra of 1-hydroxyanthraquinones is determined primarily by their tautomeric or conformational structures (Fain et al 2006). Intra- and intermolecular hydrogen bonding cause displacement towards longer wavelengths due the formation of a pseudo-ring through hydrogen bond, which increases the length of the conjugated system (Diaz 1990; 1991). …”

Section: Introductionmentioning

confidence: 99%

UV/Visible spectra of a series of natural and synthesised anthraquinones: experimental and quantum chemical approaches

et al. 2014

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Root decoctions of anthraquinone-containing plants are often taken as postpartum tonic and aphrodisiac. Anthraquinones are known for their diverse biological activities, especially antioxidant and anticancer. A series of 35 anthraquinones was generated by isolation from Rubiaceae plants and synthesis. Their UV/vis spectrum depends on the nature and relative positions of auxochromic substituents on the basic skeleton. To predict the maximum absorption bands for the current series of anthraquinones, excited sate calculations were performed using TD-DFT, CIS, ZINDO methods. The results showed that the use of PBE0 or its combination with B3LYP and B3P86 hybrid functionals are the most suitable to reproduce accurately the experimental λMAX. The structure–property relationships (SPRs) were established based on structural and electronic properties of the anthraquinones and showed (i) the importance of the number and position of OH groups and (ii) the positive contribution of the electrophilicity and hardness as electronic descriptors on position and amplitude of the maximum absorption bands.

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“…The complete conversion of 5 with Jeffamine ® M 600 is proven by the shift of the absorption maxima from 320 nm and 505 nm to higher wavelengths at 595 nm and 640 nm. According to literature, the introduction of amino groups in the 1- and 1,4-position of anthraquinones leads to a charge transfer of electrons from the amino group to the carbonyl functionality which results in additional π–π* absorption bands in the spectra of these compounds [45]. …”

Section: Resultsmentioning

confidence: 99%

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

Obels

Lievenbrück

Ritter

2016

Beilstein J. Org. Chem.

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SummaryThe double alkylation of N-vinylpyrrolidone (N-VP) with 1,8-dibromooctane yields paraffin-like oligomeric chains bearing polymerizable vinyl moieties. These oligomers were radically crosslinked in bulk with N-VP as co-monomer yielding swellable polymer disks. The vinylic side groups of the N-VP oligomers allow thiol–ene click reactions with 2-aminoethanethiol hydrochloride to obtain reactive amino-functionalized oligomers. Further modification of the free amino groups with 1,4-difluoro-9,10-anthraquinone (DFA) yields red-colored oligomeric anthraquinone dyes. The final reaction of DFA-substituted N-VP oligomers with Jeffamine® M 600 leads to blue-colored and branched oligomers with poly(ethylene glycol) side chains.

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Absorption and emission spectroscopy and photochemistry of 1,10-anthraquinone derivatives: a review

Cited by 147 publications

References 87 publications

A Metal‐Free, Nonconjugated Polymer for Solar Photocatalysis

A Metal‐Free, Nonconjugated Polymer for Solar Photocatalysis

UV/Visible spectra of a series of natural and synthesised anthraquinones: experimental and quantum chemical approaches

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

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