Growth, structural, Hirshfeld surface analysis, DFT validation on the crystal structure of 1, 10-Phenanthrolin-1-ium-5,6-dione perchlorate monohydrate

Kumaresan, S.; Asha, R. Nandini; Libiyal, J. Maria; Selvam, V.; Bhuvanesh, Nattamai; Nayagam, B. Ravindran Durai

doi:10.1016/j.cdc.2021.100706

Cited by 2 publications

(2 citation statements)

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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%

“…From these pioneering works, some minor variations in this synthesis of 867 have been described. Some authors first dissolve phen in sulfuric acid then add sodium bromide and then nitric acid (refs , , , − , , , ), others first mixed phen with potassium or sodium bromide and cool down the mixture before adding sulfuric acid and nitric acid at −78 (refs , , , , ) or 0 °C (refs , , , , , ,, , , , − ,,, , , , − , , , , ), and others cool the sulfuric acid solution at 0 or −78 °C and add a mixture of phen and KBr or NaBr then add nitric acid (refs , , , , , , , , − ). Other reports advise to cool the sulfuric acid and nitric acid at 0 °C before phen and NaBr are added to the mixture and heated, , or some directly prepare the phen and KBr solid mixture and add the latter to the acidic mixture before heating. , Finally, some authors first dissolved phen in sulfuric acid then add potassium bromide; in this case, no nitric acid was used before heating the reaction. , …”

Section: Divergent Synthesis Pathwaysmentioning

confidence: 99%

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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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