Efficient Synthesis of 1,10-Phenantroline-5,6-dione

Miltsov, Serguei; Karavan, V. S.; Borin, Veniamin

doi:10.1134/s1070363219050281

Cited by 4 publications

(3 citation statements)

References 17 publications

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“…1,10-Phenanthroline was purchased from Acros Organics, and 1,10-phenanthroline-5,6-dione was synthesized according to the reported procedure. 49 Copper( ii ) nitrate trihydrate was purchased from Vetec. All syntheses were carried out at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization, and biological evaluation of hybrid copper(ii) complexes containing azole drugs and planar ligands against neglected diseases

de Azevedo-França,

Feliciano dos Santos Ramos,

Messori

et al. 2024

New J. Chem.

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Section: Methodsmentioning

confidence: 99%

Synthesis, characterization, and biological evaluation of hybrid copper(ii) complexes containing azole drugs and planar ligands against neglected diseases

de Azevedo-França,

Feliciano dos Santos Ramos,

Messori

et al. 2024

New J. Chem.

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“…Phendione 867 is probably one of the most versatile building blocks ever used to functionalize phen. A plethora of articles describes the synthesis of 867 . ,,,− The common point to all the reported procedures is the strongly acidic (ensuring phen is protonated and increasing the solubility) and oxidizing conditions. Phendione can be further transformed into precious synthons for numerous applications.…”

Section: Divergent Synthesis Pathwaysmentioning

confidence: 99%

“…Carefully adding sulfuric acid at low temperature will limit the rapid formation of HBr. In 2019, Miltsov et al 881 proposed to modify this protocol by changing potassium bromide to molecular bromine to avoid (or minimize) the formation of HBr. The best conditions to obtain the highest yield (ca.…”

Section: Functionalization Of Phen At Positions 5 Andmentioning

confidence: 99%

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

Queffélec,

Pati,

Pellegrin

2024

Chem. Rev.

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1,10-Phenanthroline (phen) is one of the most popular ligands ever used in coordination chemistry due to its strong affinity for a wide range of metals with various oxidation states. Its polyaromatic structure provides robustness and rigidity, leading to intriguing features in numerous fields (luminescent coordination scaffolds, catalysis, supramolecular chemistry, sensors, theranostics, etc.). Importantly, phen offers eight distinct positions for functional groups to be attached, showcasing remarkable versatility for such a simple ligand. As a result, phen has become a landmark molecule for coordination chemists, serving as a must-use ligand and a versatile platform for designing polyfunctional arrays. The extensive use of substituted phenanthroline ligands with different metal ions has resulted in a diverse array of complexes tailored for numerous applications. For instance, these complexes have been utilized as sensitizers in dye-sensitized solar cells, as luminescent probes modified with antibodies for biomaterials, and in the creation of elegant supramolecular architectures like rotaxanes and catenanes, exemplified by Sauvage’s Nobel Prize-winning work in 2016. In summary, phen has found applications in almost every facet of chemistry. An intriguing aspect of phen is the specific reactivity of each pair of carbon atoms ([2,9], [3,8], [4,7], and [5,6]), enabling the functionalization of each pair with different groups and leading to polyfunctional arrays. Furthermore, it is possible to differentiate each position in these pairs, resulting in non-symmetrical systems with tremendous versatility. In this Review, the authors aim to compile and categorize existing synthetic strategies for the stepwise polyfunctionalization of phen in various positions. This comprehensive toolbox will aid coordination chemists in designing virtually any polyfunctional ligand. The survey will encompass seminal work from the 1950s to the present day. The scope of the Review will be limited to 1,10-phenanthroline, excluding ligands with more intracyclic heteroatoms or fused aromatic cycles. Overall, the primary goal of this Review is to highlight both old and recent synthetic strategies that find applicability in the mentioned applications. By doing so, the authors hope to establish a first reference for phenanthroline synthesis, covering all possible positions on the backbone, and hope to inspire all concerned chemists to devise new strategies that have not yet been explored.

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A double co-sensitization strategy using heteroleptic transition metal ferrocenyl dithiocarbamate phenanthrolene-dione for enhancing the performance of N719-based DSSCs

et al. 2022

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Efficient Synthesis of 1,10-Phenantroline-5,6-dione

Cited by 4 publications

References 17 publications

Synthesis, characterization, and biological evaluation of hybrid copper(ii) complexes containing azole drugs and planar ligands against neglected diseases

Synthesis, characterization, and biological evaluation of hybrid copper(ii) complexes containing azole drugs and planar ligands against neglected diseases

Fifty Shades of Phenanthroline: Synthesis Strategies to Functionalize 1,10-Phenanthroline in All Positions

A double co-sensitization strategy using heteroleptic transition metal ferrocenyl dithiocarbamate phenanthrolene-dione for enhancing the performance of N719-based DSSCs

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