56290-06-3

Basic information

• Product Name: 5,6-Dibromo-1,10-phenanthroline
• Synonyms: 5,6-Dibromo-1,10-phenanthroline;5,6-Dibromo-1,10-phenthroline
• CAS NO: 56290-06-3
• Molecular Formula: C₁₂H₆Br₂N₂
• Molecular Weight: 338
• Product Categories: Electronic Chemicals
• Mol File: 56290-06-3.mol

Chemical Properties

• Melting Point: 221 °C
• Boiling Point: 469.2±40.0 °C(Predicted)
• Appearance: /
• Density: 1.915±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 3.27±0.10(Predicted)
• CAS DataBase Reference: 5,6-Dibromo-1,10-phenanthroline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dibromo-1,10-phenanthroline(56290-06-3)
• EPA Substance Registry System: 5,6-Dibromo-1,10-phenanthroline(56290-06-3)

Safety Data

• Hazardous Substances Data: 56290-06-3(Hazardous Substances Data)

Usage

Uses

Used in Coordination Chemistry:
5,6-Dibromo-1,10-phenanthroline is used as a chelating agent for the formation of stable complexes with metal ions. Its ability to bind with transition metals makes it a valuable component in the study and application of coordination chemistry.
Used in Analytical Chemistry:
In analytical chemistry, 5,6-Dibromo-1,10-phenanthroline is used as a reagent for the detection and analysis of metal ions. Its interaction with metal ions allows for the development of methods to quantify and identify these elements in various samples.
Used in Catalysis:
5,6-Dibromo-1,10-phenanthroline is employed as a catalyst or a catalyst support in various chemical reactions. Its metal-chelating properties can enhance the efficiency of catalytic processes, particularly those involving transition metal catalysts.
Used in Environmental Analysis:
5,6-Dibromo-1,10-phenanthroline is used as an analytical tool in environmental chemistry to detect and measure the presence of metal ions in samples such as water, soil, and air. Its affinity for metal ions aids in monitoring and assessing environmental contamination.
Used as a Fluorescent Probe in Biological Systems:
5,6-Dibromo-1,10-phenanthroline is utilized as a fluorescent probe to study the interactions between metal ions and biological systems. Its fluorescent properties upon binding to metal ions allow researchers to observe and analyze these interactions, which is crucial in understanding metal ion roles in biological processes.

Upstream product

• 858468-10-7 5,6-dibromo-[8]quinolylamine 
• 56-81-5 glycerol 
• 66-71-7 1,10-Phenanthroline 
• 412335-29-6 5,6-dibromo-8-nitro-quinoline 
• 24108-97-2 3,4-dibromoacetanilide 
• 75293-96-8 acetic acid-(4,5-dibromo-2-nitro-anilide) 

Downstream Products

• 909103-24-8 5-bromo-6-(2-isopropyl-5-phenylthien-3-yl)-1,10-phenanthroline 
• 1141507-82-5 5,6-bis(pyren-1-ylethynyl)-1,10-phenanthroline 
• 1160652-87-8 [Rh(5,6-dibromo-1,10-phenanthroline)(CNC₆H₃Me₂-2,6)2]BF₄ 
• 1041480-39-0 5,6-bis(benzylthio)-1,10-phenanthroline 

Relevant articles and documents

Efficient access to a versatile 5,6-dithio-1,10-phenanthroline building block and corresponding organometallic complexes

(Chemical Equation Presented) A facile access to 5,6-bis(2- cyanoethylsulfanyl)-1,10-phenanthroline 1 and its ruthenium(II) bipyridil complex 2, as versatile building blocks for the straightforward synthesis of 5,6-dithio functionalized 1,10-phenanthroline based systems, is described.

Complexes with redox-active ligands: Synthesis, structure, and electrochemical and photophysical behavior of the Ru(II) complex with TTF-annulated phenanthroline

Ru(II) complexes with chelating ligands, 4′,5′- ethylenedithiotetrathiafulvenyl[4,5-f][1,10]phenanthroline (L1), 1,3-dithiole-2-thiono[4,5-f][1,10]phenanthroline (L2), and 1,3-dithiole-2-ono[4, 5-f][1,10]phenanthroline (L3), have been prepared and their structural, electrochemical, and photophysical properties investigated. Density functional theory (DFT) calculations indicate that the highest occupied molecular orbital of [Ru(bpy)2(L1)](PF6)2 (1) is located on the tetrathiafulvalene (TTF) subunit and appears ～0.6 eV above the three Ru-centered d orbitals. In agreement with this finding, 1 exhibits three reversible oxidations: the two at lower potentials take place on the TTF subunit, and the one at higher potential is due to the Ru3+/Ru 2+ redox couple. Complexes [Ru(bpy)2(L2)](PF 6)2 (2) and [Ru(bpy)2(L3)](PF6) 2 (3) exhibit only the Ru3+/Ru2+-related oxidation. The optical absorption spectra of all complexes reveal a characteristic metal-to-ligand charge transfer (MLCT) band centered around 450 nm. In addition, in the spectrum of 1 the MLCT band is augmented by a low-energy tail that extends beyond 500 nm and is attributed to the intraligand charge transfer (ILCT) transition of L1, according to time-dependent DFT calculations. The substantial decrease in the luminescence quantum yield of 1 compared to those of 2 and 3 is attributed to the reductive quenching of the emissive state via electron transfer from the TTF subunit to the Ru3+ center, thus allowing nonradiative relaxation to the ground state through the lower-lying ILCT state. In the presence of O2, complex 1 undergoes a photoinduced oxidative cleavage of the central Ci=C bond of the TTF fragment, resulting in complete transformation to 3. This photodegradation process was studied with 13C NMR and optical absorption spectroscopy.

Phenanthroline-Based Molecular Switches for Prospective Chemical Grafting: A Synthetic Strategy and Its Application to Spin-Crossover Complexes

1,10-Phenanthroline represents a well-known versatile ligand system finding many applications in chemistry, biology, and material science. The properties and thus the use of these molecules are determined by coordinating metal ions and ligand substituents. Advanced ligand systems that, for instance, feature simultaneously an integrated photochrome and a surface anchoring group require the introduction of several differing substituents and the synthesis of asymmetric derivatives. In spite of a long history of the ligand system - and to our great surprise - a general synthetic approach allowing the introduction of differing substituents at positions (3,8) and (5,6) of 1,10-phenanthroline is not known. Here, we present a general approach for the synthesis of such phenanthrolines. The approach is used to integrate a diarylethene photochrome into a functionalized phenanthroline and thus to synthesize a novel photoswitchable phenanthroline and a corresponding spin-crossover molecular photoswitch. The functionality of both the ligand and its iron(II) complex at room temperature has been demonstrated. The importance of this work for chemical grafting of molecular switches based on phenanthrolines is emphasized.

Efficient Access to 5-Bromo- and 5,6-Dibromophenanthroline Ligands

Bromo-functionalized precursor molecules are essential for generating desired target compounds through cross-coupling reactions. Herein we show an improved synthetic route, feasible at low temperatures and affording high yields, to the ligands 5-bromo-1,10-phenanthroline (1) and 5,6-dibromo-1,10-phenanthroline (2). The corresponding ruthenium complexes, containing various equivalents of ligand 2, are easily accessible in high yields, including the analogue of tris-homoleptic [Ru(bpy)3]2+ (bpy = 2,2′-bipyridine), [Ru(2)3]2+. X-ray diffraction analyses have provided detailed information on the structures of the ligands and their corresponding metal complexes. An investigation of the electrochemical properties has provided detailed information on the 3MLCT state localized on 2. We show the conversion of heteroleptic ruthenium complexes of these ligands in Suzuki cross-coupling reactions whereas the ligands did not undergo reaction under the same conditions.

Synthesis, Characterization, and Properties of Iron(II) Spin-Crossover Molecular Photoswitches Functioning at Room Temperature

Spin-crossover molecular switches [FeII(H2B(pz)2)2L] (L = novel phenanthroline-based ligands featuring photochromic diarylethene units; pz = 1-pyrazolyl) were synthesized and thoroughly characterized by variable

Synthesis of poly(1,10-phenanthroline-5,6-diyl)s having a π-stacked, helical conformation

5,6-Dibromo-1,10-phenanthroline and 2,9-di-n-butyl-5,6-dibromo-1,10-phenanthroline were polymerized using a Ni catalyst to afford helical polymers in which the phenanthroline moieties are densely stacked on top of each other. Polymerization of the latter monomer using a chiral catalyst led to a preferred-handed helix. This is the first Ni-catalyzed helix-sense-selective polymerization of aromatic compounds.

Triplet MLCT photosensitization of the ring-closing reaction of diarylethenes by design and synthesis of a photochromic rhenium(I) complex of a diarylethene-containing 1,10-phenanthroline ligand

Synthesis of the diaryle-thene-containing ligand LI based on Suzuki cross-coupling reaction between thienyl boronic acid and the dibromophenanthroline ligand is reported. On coordination to the rhenium(I) tricarbonyl complex system, the photochromism of L1 could be photosensitized and consequently extended from intraligand excitation at λ≤340nm in the free ligand to metal-to-ligand charge-transfer (MLCT) excitation atλ≤480nm in the complex. The photo-chromic reactions were studied by 1HNMR, UV/Vis, and steady-state emission spectroscopy. Photosensitization was further probed by ultrafast transient absorption and time-resolved emission spectroscopy. The results provided direct evidence that the formation of the closed form by the MLCT-sensitized photochromic process was derived from the 3MLCT excited state. This supports the photosensitization mechanism, which involves an intramolecular energy-transfer process from the 3MLCT to the 3IL(L1) state that initiated the ring-closure reaction. The photophysical and electrochemical properties of the complex were also investigated.

PHOTOCHROMIC DIARYLETHENE-CONTAINING COORDINATION COMPOUNDS AND THE PRODUCTION THEREOF

Diarylethene-containing ligands and their coordination compounds are described. The ligands display photochromism with UV excitation, while the coordination compounds display photochromism with both excitation in the UV region and excitation into lower en