Aza-bridged bis-1,10-phenanthroline acyclic derivatives: synthesis, structure, and regioselective alkylation

Kao, Hsien-Chang; Hsu, Chia‐Jung; Hsu, Che-Wei; Lin, Chien-Ho; Wang, Wen-Jwu

doi:10.1016/j.tetlet.2010.05.039

Cited by 10 publications

(4 citation statements)

References 14 publications

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“…Also, the absence of C–Cl stretching at 674 and 1264 cm –1 suggested that the loading of the ligand on the polymer matrix was complete. For converting 2-chloro- to 2-amino-1,10-phenanthroline, a lot of work has been done up to date. , The reactions have been carried out at high temperature and pressure conditions using high boiling point solvents such as phenol, acetamide, etc., which have some inherent disadvantages . Distillation of these high boiling solvents is an important step in the isolation of the product, but in most cases that results in lower yields and difficulty in operating conditions.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Polymer-Bound Penta-aza Ligand for Selective Adsorptive Separation of Cobalt(II) from Zirconium(IV)

Kumar

Madyal

Joshi

et al. 2011

Ind. Eng. Chem. Res.

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A penta-aza ligand was designed using the Density Functional Theory (DFT), synthesized, and then loaded on a polystyrene matrix to prepare a functional polymer as a Co(II) selective adsorbent. A comparative experimental study on adsorption of Co(II) and Zr(IV) revealed that the polymer-supported ligand is more selective toward Co(II) than Zr(IV) from aqueous acidic solutions. The maximum adsorption capacities of the adsorbent for Co(II) and Zr(IV) were 4.1 and 0.5 mg/g, respectively, at pH 1.0. Vibrational frequencies of the metalÀligand complexes were calculated with the VWN-BP functional to confirm true local minima.

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Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Polymer-Bound Penta-aza Ligand for Selective Adsorptive Separation of Cobalt(II) from Zirconium(IV)

Kumar

Madyal

Joshi

et al. 2011

Ind. Eng. Chem. Res.

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“…Metal ion-templated syntheses (Cu, Ni, and Co) of this molecule have been proposed, but the same molecule can be prepared by reacting 396 with gaseous ammonia at high temperature (Scheme ). In similar conditions, when 396 was used as electrophile, open cycle 503 was obtained as a planar tetradentate ligand, which has been used for example to coordinate Pt or Ru for the design of cytotoxic drugs or molecular catalysts, respectively. 503 could be easily alkylated either on the nitrogen atoms of phen (yielding 504 ) or on the bridging nitrogen atom (yielding 505 ) depending on the experimental conditions (CH 2 Cl 2 at room temperature vs DMSO at 110 °C respectively).…”

Section: Divergent Synthesis Pathwaysmentioning

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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“…This phenomenon suggested a planar geometry of Pt complexes would be essential for the high stabilization effect on Gquadruplex. The X-ray crystal structure of acidified bpa ligand was previously reported to be a near planar structure, since the aza-bridge can facilitate the two phenanthrolines to form an intramolecular H-bond network and to overcome the electron repulsion among the C2 hydrogens of the two phen rings (scheme 1) [49].…”

Section: Synthesis Of [Pt(bpa)] 2+ Complexes With Planar Structurementioning

confidence: 99%

“…For the synthesis of two Pt complexes, the bpa ligand was firstly synthesized as previously report [49,50]. After basified the bpa ligand, alkylation of the amino group as aza-bridge was carried out by refluxing bpa in dimethyl sulfoxide in the presence of KOH and alkylation agents (iodomethane or 1-(2-chloroethyl)piperidine).…”

Section: Scheme 1 Synthesis Of the Platinum Complexesmentioning

confidence: 99%

Aza-bridged bisphenanthrolinyl Pt(II) complexes: Efficient stabilization and topological selectivity on telomeric G-quadruplexes

Meng

Xie

et al. 2017

Journal of Inorganic Biochemistry

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Aza-bridged bis-1,10-phenanthroline acyclic derivatives: synthesis, structure, and regioselective alkylation

Cited by 10 publications

References 14 publications

Design and Synthesis of Polymer-Bound Penta-aza Ligand for Selective Adsorptive Separation of Cobalt(II) from Zirconium(IV)

Design and Synthesis of Polymer-Bound Penta-aza Ligand for Selective Adsorptive Separation of Cobalt(II) from Zirconium(IV)

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

Aza-bridged bisphenanthrolinyl Pt(II) complexes: Efficient stabilization and topological selectivity on telomeric G-quadruplexes

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