130897-87-9

Usage

Uses

Used in Analytical Chemistry:
1,10-Phenanthroline-4,7-dicarboxaldehyde is used as a reagent for the determination of metals, particularly in the form of their complexes with the ligand phenanthroline. It is instrumental in the detection and quantification of metal ions through its ability to form colored or fluorescent complexes, which can be measured using spectrophotometric and fluorometric methods.
Used in Biological Sample Analysis:
In the field of biology, 1,10-Phenanthroline-4,7-dicarboxaldehyde is used as a detection agent for metals in biological samples. Its complexes with metal ions can be quantified, providing insights into metal concentrations in biological systems, which is crucial for understanding metal-related biological processes and potential toxicity.
Used in Environmental Sample Analysis:
1,10-PHENANTHROLINE-4,7-DICARBOXALDEHYDE is also utilized in environmental analysis, where it helps in the detection and quantification of metal contaminants in various environmental samples such as water, soil, and air. The ability to accurately measure metal concentrations is essential for environmental monitoring and ensuring compliance with environmental regulations.
Used in Industrial Process Stream Analysis:
1,10-Phenanthroline-4,7-dicarboxaldehyde is employed in industrial settings to monitor metal concentrations in process streams. Its use in this context aids in maintaining process efficiency and product quality by ensuring that metal impurities are kept within acceptable limits.
Used in the Synthesis of Coordination Compounds:
In addition to its analytical applications, 1,10-Phenanthroline-4,7-dicarboxaldehyde is used in the synthesis of coordination compounds. These compounds have a wide range of applications, including as catalysts, sensors, and materials with unique electronic or magnetic properties.
Used in Medicinal and Materials Chemistry:
Furthermore, 1,10-Phenanthroline-4,7-dicarboxaldehyde serves as a building block for the construction of complex organic molecules in medicinal chemistry, potentially leading to the development of new pharmaceuticals. In materials chemistry, it contributes to the creation of advanced materials with specific properties tailored for various applications.

Upstream product

• 3248-05-3 4,7-Dimethyl-1,10-phenanthroline 

Downstream Products

• 1340599-16-7 4,7-bis(benzoyloxymethyl)-1,10-phenanthroline 
• 31301-31-2 1,10-phenanthroline-4,7-dicarboxylic acid 

Relevant academic research and scientific papers

Color responses of novel receptors for AcO- and a test paper for AcO- in pure aqueous solution

An efficient AcO- sensor L which contains 1,10-phenanthroline-based and nitrophenylhydrazine-based groups, and its water-soluble Ru(II) complex were synthesized, characterized and studied in this Letter. Via UV-vis experiments and 1H NMR titration in DMSO solution, it was found that there were potential hydrogen bonds between the N{double bond, long}CH and AcO- after the deprotanation of two -NH during the reaction of L or its Ru complex with anions. Furthermore, an easy-to-prepare test paper was developed to detect AcO- at 10 mg/L in pure aqueous solution.

A new efficient photosensitizer for nanocrystalline solar cells: Synthesis and characterization of m-bis(4,7-dicarboxy-l,10phenanthroline)dithiocyanato ruthenium(n)

The complexes [NBu4]2-n[a.y-Ru(H2-xdcphen)2X 2 (n = 0 or 1; H2dcphen; =4,7-dicarboxy-l,10-phenanthroline; X = Cl, CN or SCN) were synthesized and spectroscopically characterized as a new class of photosensitizers. The energy levels of the LUMO and HOMO of ra-[Ru(H2dcphen)2(NCS)2] were estimated to be -1.02 and 0.89 V (vs. SCE), respectively, slightly more positive than those of [NBu4]2n[m-Ru(H2-xdcbpy)2(NCS) 2] (x = 0 or 1 ; H2dcbpy = 4,4'-dicarboxy-2,2'-bipyridine). A more intense and broader MLCT absorption of [NBu4]2[raeRu(H2-xdcphen)2(NCS)2] (;; = 0 or 1 ) than that of [NBu4]2-x[rae-Ru(H1-xdcbpy) 2(NCS)2] (;; = 0 or 1) was observed in ethanol solution at around 525 nm in the visible region. It is demonstrated that the new complexes act as efficient light harvesting antennae for dye-sensitized solar cells. A [NBu4]2-x[cw-Ru(Hdcphen)2(NCS)2] sensitized nanocrystalline TiO2 film shows a remarkable solar light to electrical power conversion efficiency of 6.1% at 100mWcm-2of AM 1.5. The Royal Society of Chemistry 2000.

BODIPY-functionalized 1,10-phenanthroline as a long wavelength sensitizer for near-infrared emission of the ytterbium(iii) ion

Two BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) moieties were chemically appended to the 4,7-positions of 1,10-phenanhtroline resulting in two new ligands (BODIPY-Phen and 4I-BODIPY-Phen) with strong absorption at 507 nm and 540 nm, respectively. BODIPY-Phen emits fluorescence strongly centered at 507 nm, whereas the fluorescence of 4I-BODIPY-Phen was completely quenched due to the introduction of four I atoms at its 2,6 positions. The two ligands reacted readily with tris(1,1,1,5,5,5-hexafluoro-2,4-pentanedionate) ytterbium(iii) dihydrate through substitution reactions forming eight-coordinate complexes that emit strongly at 976 nm upon excitation at their absorption maximal positions. Both complexes exhibited a lifetime of ～11 μs in dichloromethane at room temperature.

Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors

Among 18 human chemokine receptors, CCR1, CCR4, CCR5, and CCR8 were activated by metal ion Zn(II) or Cu(II) in complex with 2,2′-bipyridine or 1,10-phenanthroline with similar potencies (EC50 from 3.9 to 172 μM). Besides being agonists, they acted as selective allosteric enhancers of CCL3. These actions were dependent on a conserved glutamic acid at TM-7 (VII:06/7.39). A screening of 20 chelator analogues in complex with Zn(II) identified compounds with increased potencies, with 7 reaching highest potency at CCR1 (EC50 of 0.85 μM), 20 at CCR8 (0.39 μM), and 8 at CCR5 (1.0 μM). Altered selectivity for CCR1 and CCR8 over CCR5 (11, 12) and a receptor-dependent separation of allosteric from intrinsic properties were achieved (20). The pocket similarities of CCR1 and CCR8, contrary to CCR5 as proposed by the ligand screen, were elaborated by computational modeling. These studies facilitate exploration of chemokine receptors as possible targets for therapeutic intervention.

A BODIPY-functionalized PdII photoredox catalyst for Sonogashira C-C cross-coupling reactions

We report for the first time a BODIPY-functionalized dichloro(1,10-phenanthroline)palladium(ii) complex as an efficient photoredox catalyst for the Sonogashira C-C cross-coupling between phenylacetylene derivatives and iodobenzene derivatives with yields

Surface immobilized copper(i) diimine photosensitizers as molecular probes for elucidating the effects of confinement at interfaces for solar energy conversion

Heteroleptic copper(i) bis(phenanthroline) complexes with surface anchoring carboxylate groups have been synthesized and immobilized on nanoporous metal oxide substrates. The species investigated are responsive to the external environment and this work provides a new strategy to control charge transfer processes for efficient solar energy conversion.

A Simple and Selective Fluorescent Sensor for Zn2+ and H+ Ions in Aqueous Solution with OR Logic Gate Function

The synthesis and properties of a new compound, viz., (N,N′-[1,10-phenanthroline-4,7-diyldi((E)methylylidene)]bis(1,10-phenanthrolin-5-amine) (1), is described. Compound 1 can be used as a selective fluorescent Zn2+ sensor in buffered solution. Furthermore, 1 induces turn on fluorogenic response to H+ ions. Finally, it is shown that an OR logic gate can be constructed with 1 by using Zn2+ and H+ as two-inputs. [Figure not available: see fulltext.]

Synthesis and DNA-binding properties of 1,10-phenanthroline analogues as intercalating-crosslinkers

(Chemical Equation Presented) We synthesized a series of bis(bromomethyl)4 ,10-phenanthrolines as novel anticancer lead compounds and examined their DNA-binding properties. 5,6-Bis(bromomethyl)-1,10-phenanthroline showed DNA intercalating activity and DNA crosslinking activity, furthermore it is stable in aqueous solution.

A Fluorescent Hypochlorite Probe Built on 1,10-Phenanthroline Scaffold and its Ion Recognition Features

In this study, the synthesis of 7-((Hydroxyimino)methyl)-1,10-phenanthroline-4-carbaldehyde oxime (1) in two steps starting from 4,7-dimethyl-1,10-phenanthroline (2) is reported. It is found that compound 1 can be used as a fluorogenic probe for the detection of hypochlorite ion in aqueous solution. NMR and mass spectral analysis indicate that probe 1 undergoes a chemical transformation through its oxime units upon treatment with hypochlorite, which results in a remarkable enhancement of the emission intensity. Also, metal ion recognition properties of probe 1 is investigated. It is noted that compound 1 is responsive to Zn2+, Cd2+, Ni2+ and Cu2+ metal ions, which reduced the emission intensity under identical conditions.

Rapid and highly sensitive dual-channel detection of cyanide by bis-heteroleptic ruthenium(II) complexes

Two new ruthenium complexes [Ru(bipy)2(PDA)]2+ (1) and [Ru(phen)2(PDA)]2+ (2) (PDA = 1,10-phenanthroline-4,7- dicarboxaldehyde) have been synthesized to detect cyanide based on the well-known formation of cyanohydrins. Both 1[PF6]2 and 2[PF6]2 were fully characterized by various spectroscopic techniques and their solid state structures determined by single-crystal X-ray diffraction. Their anion binding properties in pure and aqueous acetonitrile were thoroughly examined using two different channels, i.e., UV-vis absorption and photoluminescence (PL). After addition of only 2 equiv of CN-, the PL intensity of 1[PF6]2 and 2[PF6] 2 was enhanced ～55-fold within 15 s along with a diagnostic blue shift of the emission by more than 100 nm. PL titrations of 1[PF 6]2 and 2[PF6]2 with CN- in CH3CN furnished the very high overall cyanohydrin formation constants log β[CN-] = 15.36 ± 0.44 (β[CN-] = 2.3 × - 1015 M-2) and log β[CN-] = 16.37 ± 0.53 (β[CN-] = 2.3 × 1016 M-2), respectively. For both probes, the second constant, K2, is about 57-84 times less than K1, suggesting that the cyanohydrin reaction is stepwise. The stepwise mechanism is further supported by results of a 1H NMR titration of 2[PF 6]2 with CN-. The high selectivity of 2[PF 6]2 for CN- was established by PL in the presence of other competing anions. Furthermore, the color change from orange-red to yellow and the appearance of a orange luminescence, which can be observed by the naked eye, provides a simple real-time method for cyanide detection. Finally, theoretical calculations were carried out to elucidate the details of the electronic structure and transitions involved in the ruthenium probes and their cyanide adducts.