54258-41-2

Usage

Uses

Used in Organic Light-Emitting Devices (OLEDs):
(1,10)PHENANTHROLIN-5-YLAMINE is used as a key component in the synthesis of bis-[1,10]phenanthrolin-5-yl-pyromellitic diimide (Bphen-PMD). (1,10)PHENANTHROLIN-5-YLAMINE finds applications in the development of organic light-emitting devices, which are widely used in display technologies and lighting systems due to their high efficiency, low power consumption, and thin, flexible design.
Used in DNA Detection:
As a potential fluorescent label, (1,10)PHENANTHROLIN-5-YLAMINE plays a crucial role in the field of molecular biology, particularly in DNA detection. Its fluorescence properties enable the identification and analysis of specific DNA sequences, which is essential for various research and diagnostic applications.
Used in Biosensors and Biofuel Cells:
(1,10)PHENANTHROLIN-5-YLAMINE is utilized as a mediator for glucose oxidase in the development of biosensors and biofuel cells. Its ability to facilitate electron transfer between the enzyme and the electrode surface enhances the sensitivity and efficiency of these devices, making them valuable tools for monitoring glucose levels in various applications, such as diabetes management and environmental monitoring.

InChI:InChI=1/C12H9N3/c13-10-7-8-3-1-5-14-11(8)12-9(10)4-2-6-15-12/h1-7H,13H2

Upstream product

• 4199-88-6 5-Nitro-1,10-phenanthroline 
• 66-71-7 1,10-Phenanthroline 
• 41148-68-9 5-nitro-phenanthroline 

Downstream Products

• 163628-20-4 5-oxo-5-(1,10-phenanthrolin-5-ylamino)pentanoic acid 
• 75618-99-4 5-isothiocyanato-1,10-phenanthroline 
• 1147124-95-5 [Ru(η2-Ph2PC2H2PPh2)(trifluoroacetate)(CO)(5-amino-1,10-phenanthroline)]PF6 
• 1207283-21-3 N-[(1E,2E)-3-phenyl-prop-2-en-1-ylidene]-1,10-phenanthrolin-5-amine 
• 1387578-22-4 2-((E)-(1,10-phenanthroline-5-ylimino)methyl)phenol 
• 1252660-13-1 N-((9-((4-(5(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)phenoxy)hexyl)-9H-carbazol-3-yl)methylene)-1,10-phenanthrolin-5-amine 
• 1252660-14-2 N-((9-((4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)phenoxy)hexyl)-9H-carbazol-3-yl)methylene)-1,10-phenanthrolin-5-amine 
• 1252660-10-8 N-((9-((4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenoxy)hexyl)-9H-carbazol-3-yl)methylene)-1,10-phenanthrolin-5-amine 
• 1252660-11-9 N-((9-((4-(5(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)phenoxy)hexyl)-9H-carbazol-3-yl)methylene)-1,10-phenanthrolin-5-amine 
• 1252660-12-0 N-((9-((4-(5-p-tolyl-1,3,4-oxadiazol-2-yl)phenoxy)hexyl)-9H-carbazol-3-yl)methylene)-1,10-phenanthrolin-5-amine 
• 1338056-16-8 C₅₅H₈₅N₃O₄ 
• 1433748-05-0 C₆₂H₄₅N₉O 
• 1433748-09-4 C₇₄H₆₁N₉O₃ 
• 84537-86-0 bis(2,2′-bipyridine)(5-aminophenanthroline)ruthenium bis(hexafluorophosphate) 

Relevant academic research and scientific papers

Self-assembly of novel molecular complexes of 1,10-phenanthroline and 5-amino-1,10-phenanthroline and evaluation of their in vitro antitumour activity

Novel molecular complexes of 1,10-phenanthroline (phen) and 5-amino-1,10-phenanthroline (5-NH2-phen) [(5-NH2-phen) 2(phen) (H2O)3 (1), (phen) 2(imidazole) (H+) (BF4-) (2), (phen)2(benzimidazole) (H+) (BF4-) (3), (5-NH2-phen)4(H2O)3 (4), and (phen)3 (indole) (H+) (BF4-) (5)] were synthesized via self-assembly processes and their in vitro anticancer activity was investigated. The structures of the compounds were confirmed by UV, FTIR, CIMS(CH4) and elemental analysis. The crystal structure of 2 was determined by X-ray diffraction. Cytotoxicity of the substances was measured using the cultivated human tumour cell lines HepG2, HEp-2, and 8-MB-GA. The tested substances showed different activity depending on the cell line and amount used. Substances 2 and 3 were not toxic to the non-tumour cells (Lep-3), but significantly toxic to all tumour ones. This is not the case with compounds 4 and 5, which are non-toxic towards carcinogenic cell lines, but even stimulate both HepG2 and HEp-2.

The oxime bond formation as an efficient tool for the conjugation of ruthenium complexes to oligonucleotides and peptides

A convenient method for the conjugation of ruthenium complex on oligonucleotides and peptides through chemoselective oxime linkage is reported. Novel Ru(II) complexes sustaining an aminooxy containing ligand were prepared and efficiently coupled with the oligonucleotides and peptides functionalized with the complementary reactive aldehyde group. The method described herein could be a useful tool for preparing a broad range of metal complex-oligonucleotide and peptide conjugates.

Organic-inorganic hybrid nanomaterial as a new fluorescent chemosensor and adsorbent for copper ion

Functionalized silica nanotube (FSNT) possessing the phenanthroline moiety as a fluorescent receptor was fabricated by sol-gel reaction, and the binding ability of FSNT with metal ions was evaluated by fluorophotometry. The Royal Society of Chemistry 2006.

Synthesis and biological activity of novel heavy metal complexes of 5-amino-1, 10-phenanthroline and 1,10-phenanthroline

Novel heavy metal complexes: Sr(5-NH2-phen)4(NO 3)(OH)(H2O)2 (1) (synthesized via a static self-assembly process) and Sn(phen) (NO3)(OH)(H2O) (2), Sn(5-NH2-phen)(OH)(Cl)(H2O) (3), Pb(5-NH 2-phen)(NO3)2(H2O) (4) (obtained via metal competitive reactions under mild conditions) were reported. The coordination compounds were characterized by elemental analysis, FTIR-spectroscopy and FAB-mass spectrometry. Their cytotoxicity was measured by MTS-test towards human tumour (MDA-MB-231, HT-29, HeLa, HepG2) and non-tumour diploid (Lep-3) cell lines. The most pronounced cytotoxic effect on all cancer lines showed 1 and 4 at their high concentrations as well as 1 at its lower ones (≤ 4×10-2 mg). Therefore, strontium complex of 5-amino-o-phenanthroline (1) exhibited the widest antitumour spectrum activity, having no toxicity to non-tumour cells at quantities ≤ 4×10 -2 mg. The computed EC50 values of 1-4 against MDA-MB-231, HT-29, HeLa, HepG2 varied from 1.40×10-3 to 6.31×10 -6 M. Towards Lep-3 substances 2-4 showed IC50 7.52×10-4 - 0.44 M. Substance 1 possess EC50=1. 26×10-7 M to the non-tumour cells. Versita Sp. z o.o.

Interaction of sulfonated ruthenium(ii) polypyridine complexes with surfactants probed by luminescence spectroscopy

Novel anionic [RuL2L′]2- complexes, where L stands for (1,10-phenanthroline-4,7-diyl)bis(benzenesulfonate) (pbbs; 3a) or (2,2′-bipyridine)-4,4′-disulfonate (bpds; 3b), and L′ is N-(1,10-phenanthrolin-5-yl)tetradecanamide (pta; 2a) or N-(1,10-phenanthrolin-5-yl)acetamide (paa; 2b), were synthesized, and their interaction with the prototypical surfactants sodium dodecylsulfate (SDS), cetyl trimethyl ammonium bromide (CTAB), and Triton X-100 (TX-100) was investigated by electronic absorption, luminescence spectroscopy, emission-lifetime determinations, and O2-quenching measurements. [Ru(bpds)2(pta)]2- (5a) displayed cooperative self-aggregation in aqueous medium at concentrations above 1.3 μM; the observed association was enhanced in the presence of either β-cyclodextrin or NaCl. This amphiphilic Ru11 compound showed the strongest interaction with all the detergents tested: nucleation of surfactant molecules around the luminescent probe was observed below their respective critical micellar concentrations. As much as a 12-fold increase of the emission intensity and a 3-fold rise in the lifetime were measured for 5a bound to TX-100 micelles; the other complexes showed smaller variations. The O2-quenching rate constants decreased up to 1/8 of their original value in H2O (e.g., for [Ru(bpds)2(pta)]2- (6a) bound to CTAB micelles). Luminescence-lifetime experiments in H2O/D2O allowed the determination of the metal-complex fraction exposed to solvent after binding to surfactant micelles. For instance, such exposure was as low as 25% for pta complexes · CTAB aggregates. The different behaviors observed were rationalized in terms of the Ru11 complex structure, the electrostatic/hydrophobic interactions, and the probe environment.

An efficient synthesis of enantiomerically pure Δ- and Λ-ruthenium(II)-labelled oligonucleotides

The synthesis of a novel tris(bidentate ligand)ruthenium(II) complex 7 and its efficient tethering to the 5'-end of oligonucleotides is described. The resulting Δ- and Λ-isomeric ruthenium(II)-labelled oligonucleotides 10a-c and 11a-d were separated either by reversed-phase HPLC or by polyacrylamide gel electrophoresis. The diastereoisomerically pure isomers were fully characterized by UV/VIS and CD spectroscopy, mass spectrometry, and enzymatic digestion with base analysis. We also investigated the thermal denaturation of the hybridized double strands.

N-Phenanthroline glycosylamines: Synthesis and copper(II) complexes

A series of novel N-(1,10-phenanthrolin-5-yl)-β-glycopyranosylamines was obtained with excellent stereoselectivity and synthetically useful yields by treatment of 5-amino-1,10-phenanthroline with different unprotected monosaccharides, using (NH4)2SO4 as an efficient promoter. Copper(II) complexes having a 2:1 mole ratio of the bidentate ligand phenanthroline N-glycoside and the metal were also prepared.

Selective fluorescent sensing of chloride

The urea functionalised phenanthroline sensor 1, which was characterised by several methods, including X-ray crystallography, gives rise to large changes in the fluorescence emission spectra upon interaction with several anions such as acetate, phosphate,

Metal coordination as a tool for controlling the self-assembling and gelation properties of novel type cholic amide-phenanthroline gelating agent

(3α,7α,12α)-Trihydroxy-N-[1,10-phenanthrolin-5-yl]- 5β-cholan-24-amide was found to be a powerful gelating agent for methanol-water in gelator to solvent ratio starting from 0.1% in absence of metal ion. Formation of phenanthroline-zinc (II) 2:1 complex changes dramatically gelating properties; when stored, it dissolves into clear solution without Tyndall effect and this solution, when heated to ca. 70°C reversibly forms a gel again, without chemical change as proven by NMR spectrometry. Structures of the gels of cholic amide-phenanthroline and its Zn2+ complex were studied by SEM.

Different morphological organic-inorganic hybrid nanomaterials as fluorescent chemosensors and adsorbents for CuII ions

Functionalized silica nanotubes (FSNT), functionalized mesoporous silica (FMS), and functionalized silica nanoparticles (FSNP-15) with an immobilized phenanthroline moiety as a fluorescent receptor were fabricated by a sol-gel reaction, and their binding abilities with metal ions were evaluated by fluorophotometry in water/acetonitrile (8:2, v/v) at pH 7. They selectively recognized Cu2+ ions among other metal cations such as Co 2+, Cd2+, Hg2+, Ni2+, Fe 3+, Ag+, Pb2+, and Zn2+, because the Cu2+ ion selectively binds to the nitrogen atoms of the phenanthroline moiety. Among the three silica nanomaterials with the immobilized receptor 1, the sensitivity of FSNT for Cu2+ ions is better than those of FMS and FSNP-15, indicating that the adsorption capacity for metal ions is dependent on the shape and surface area of the supporting nanomaterials. FSNT (10 mg) adsorb 75% of the Cu2+ ions (2.0 × 10-4 mM) while FSNP-15 (10 mg) adsorb only 36%. The detection limit of FSNT for Cu2+ ions was ca. 3.0 × 10-8 M. FSNT and FMS can be easily renewed by treatment with a solution of HCl and tetrabutylammonium hydroxide. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.