1,8-Dihydroxyanthraquinone

Catalog	BBC117102
CAS	117-10-2
Structure
Synonyms	1,4,5,8-Tetroxyantraquinone
IUPAC Name	1,8-Dihydroxyanthracene-9,10-dione
Molecular Weight	240.21
Molecular Formula	C14H8O4
Canonical SMILES	C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
InChI	InChI=1S/C14H8O4/c15-9-5-1-3-7-11(9)14(18)12-8(13(7)17)4-2-6-10(12)16/h1-6,15-16H
InChI Key	QBPFLULOKWLNNW-UHFFFAOYSA-N
Boiling Point	342.92 °C
Melting Point	191-193 °C (lit.)
Purity	98%
Density	1.303 g/ml
Appearance	Powder
pKa	6.27±0.20
Solubility in Water	Insoluble

Case Study

1,8-Dihydroxyanthraquinone for Flexible Supercapacitor Hydrogel Electrodes

Yang, Yuying, et al. Journal of Energy Storage 178 (2026): 123750.

Background
1,8-Dihydroxyanthraquinone (DHAQ) is a redox-active organic molecule with potential for electrochemical energy storage. However, its limited electrical conductivity and cycling durability can restrict electrode performance.
Application
1,8-Dihydroxyanthraquinone was used as the electrochemically active component to prepare a DHAQ/reduced graphene oxide (rGO)/polyvinyl alcohol (PVA) composite hydrogel electrode for flexible solid-state supercapacitors.
Experimental Approach
DHAQ was dissolved in DMF and mixed with an aqueous graphene oxide (GO) dispersion, followed by hydrothermal treatment at 180 °C for 12 h to obtain the DHAQ/rGO composite. The composite was subsequently dispersed in water with PVA and subjected to three freeze-thaw cycles to form flexible DGP hydrogel electrodes. A symmetric supercapacitor was assembled using PVA/H₂SO₄ as the hydrogel electrolyte.
Results
The optimized DGP electrode delivered an areal capacitance of 507.4 mF cm⁻² at 1 mA cm⁻² and maintained stable electrochemical performance under bending and torsional deformation. The assembled flexible device achieved an areal capacitance of 197.6 mF cm⁻² and an energy density of 39.3 μWh cm⁻² at 623.8 μW cm⁻². After 10,000 charge-discharge cycles, the capacitance retention remained 82.4%. DFT calculations indicated that stable parallel π-π stacking between DHAQ and rGO, together with oxygen-mediated interfacial interactions, contributed to electrode stability.
Conclusion
1,8-Dihydroxyanthraquinone demonstrated effective application as a redox-active component in flexible DHAQ/rGO/PVA hydrogel electrodes, supporting research into organic-molecule-based flexible energy-storage devices.

1,8-Dihydroxyanthraquinone for Electrochemical Detection of Copper Cyanide Complexes

Cardenas-Riojas, Andy A., et al. Journal of Electroanalytical Chemistry 880 (2021): 114909.

Background
1,8-Dihydroxyanthraquinone (1,8-DHAQ) is a redox-active anthraquinone derivative with favorable interfacial electrochemical properties. Its adsorption onto carbon electrodes provides a functional platform for analytical sensing.
Application
1,8-Dihydroxyanthraquinone was used to modify a glassy carbon (GC) electrode for the electrochemical detection and quantification of the copper cyanide complex [Cu(CN)₃]²⁻ in alkaline copper-plating bath effluents.
Experimental Approach
A 1,8-DHAQ-modified GC electrode was prepared and characterized using electrochemical impedance spectroscopy, Raman spectroscopy, and UV-Visible spectroscopy. Differential pulse voltammetry (DPV) was employed for [Cu(CN)₃]²⁻ detection. DFT calculations were further used to investigate the molecular arrangement and electrode-modifier interactions.
Results
The 1,8-DHAQ/GC sensor exhibited good reproducibility and a linear response over 5.50 × 10⁻⁷-3.81 × 10⁻⁶ mol L⁻¹, with an R² of 0.995. The reported LOD and LOQ were 1.20 × 10⁻⁶ and 3.97 × 10⁻⁶ mol L⁻¹, respectively. The sensor showed robustness toward Cl⁻, NO₃⁻, SO₄²⁻, and CO₃²⁻ interferents. DFT analysis indicated an approximately parallel arrangement of bis(1,8-DHAQ) on graphene domains through noncovalent π-π interactions. Recovery values of 95.52-97.87% were obtained for real copper electrodeposition-bath samples.
Conclusion
1,8-Dihydroxyanthraquinone enabled the construction of a reproducible carbon-electrode sensor for electrochemical analysis of copper cyanide complexes in plating effluents.

1,8-Dihydroxyanthraquinone for the Preparation of Pb(II)-Selective MOF Adsorbents

Zhao, Jiling, et al. Journal of Industrial and Engineering Chemistry 83 (2020): 111-122.

Background
1,8-Dihydroxyanthraquinone (DHAQ) provides hydroxyl and carbonyl functional groups capable of coordinating metal ions, making it a useful functional ligand for the development of selective adsorbent materials.
Application
1,8-Dihydroxyanthraquinone was used to functionalize amino-modified UiO-66-NH₂, producing a MOF-based adsorbent (MOFs-DHAQ) for selective removal of Pb(II) from wastewater.
Experimental Approach
UiO-66-NH₂ was modified with DHAQ and evaluated for Pb(II) adsorption under different pH, kinetic, temperature, and concentration conditions. Regeneration experiments, competitive-ion tests, and column adsorption studies were conducted to assess practical performance. DFT calculations were used to investigate the Pb(II)-binding configuration.
Results
At pH 4 and 298 K, MOFs-DHAQ reached adsorption equilibrium within 30 min, with a maximum Pb(II) adsorption capacity of 213.3 mg/g. The adsorption behavior followed the pseudo-second-order kinetic and Freundlich isotherm models, indicating predominantly multilayer chemisorption. Increasing temperature enhanced Pb(II) uptake, consistent with a spontaneous endothermic process. The adsorbent maintained selective Pb(II) removal in the presence of competing ions and could be regenerated for at least four adsorption-desorption cycles. In column experiments, the calculated adsorption capacity was 108.04 mg/g, close to the Thomas-model value of 109.63 mg/g. DFT calculations indicated Pb(II) coordination through monodentate N and bidentate O donor sites.
Conclusion
1,8-Dihydroxyanthraquinone enabled functionalization of UiO-66-NH₂ to produce a recyclable and Pb(II)-selective MOF adsorbent for wastewater treatment research.