197969-58-7

Usage

Uses

Used in Research Applications:
2,7-Dibromo-9,9-diethylfluorene is utilized as a research compound for studying its chemical properties and potential applications in organic synthesis. Its unique structure allows researchers to explore its reactivity and behavior in different chemical environments.
Used as an Intermediate in Organic Synthesis:
In the chemical industry, 2,7-Dibromo-9,9-diethylfluorene serves as an intermediate in the synthesis of other organic compounds. Its bromine atoms facilitate various chemical reactions, making it a valuable halogenating agent in organic chemistry.
Used in Catalytic Reactions:
The bulky ethyl groups present in 2,7-Dibromo-9,9-diethylfluorene provide steric hindrance, which can be advantageous in certain catalytic reactions. This property makes it a useful component in the development of catalysts for specific chemical processes.

InChI:InChI=1/C17H16Br2/c1-3-17(4-2)15-9-11(18)5-7-13(15)14-8-6-12(19)10-16(14)17/h5-10H,3-4H2,1-2H3

Upstream product

• 2294-79-3 9,9-diethyl-9H-fluorene 
• 74-96-4 ethyl bromide 
• 16433-88-8 2,7-dibromo-9H-fluorene 
• 106-94-5 propyl bromide 
• 75-03-6 ethyl iodide 
• 86-73-7 9H-fluorene 

Downstream Products

• 862847-75-4 2-(2'-bromo-9',9'-diethylfluorene-7'-yl)-9,9-diethylfluorene 
• 1257582-69-6 C₂₆H₂₉BrSi 
• 1245642-78-7 2-bromo-7-(4-(diphenylamino)phenyl)-9,9-diethylfluorene 
• 1245649-43-7 5-(2-(4-(diphenylamino)phenyl)-9,9-diethylfluorene-7-yl)-3-hexylthiophene-2-carbaldehyde 
• 1245652-56-5 3-(5-(2-(4-(diphenylamino)phenyl)-9,9-diethylfluorene-7-yl)-3-hexylthiophene-2-yl)-2-cyanoacrylic acid 
• 701971-75-7 N,N-di(3-hydroxyphenyl)-7-(benzothiazol-2-yl)-9,9-diethylfluoren-2-amine 
• 701971-73-5 N,N-di(3-methoxyphenyl)-7-(benzothiazol-2-yl)-9,9-diethylfluoren-2-amine 
• 1190833-67-0 7-(benzo[d]thiazol-2-yl)-9,9-diethyl-N,N-bis(3-(4-nitrophenoxy)phenyl)-9H-fluoren-2-amine 
• 1190833-68-1 N,N-bis(3-(4-aminophenoxy)phenyl)-7-(benzo[d]thiazol-2-yl)-9,9-diethyl-9H-fluoren-2-amine 
• 1370605-04-1 N,N-di(4-hydroxyphenyl)-7-(benzothiazol-2-yl)-9,9-diethyl-fluoren-2-amine 
• 1370605-03-0 N,N-di(4-methoxyphenyl)-7-(benzothiazol-2-yl)-9,9-diethyl-fluoren-2-yl-amine 
• 1370605-05-2 N,N-Di[4-(4-nitrophenoxy)phenyl]-7-(benzothiazol-2-yl)-9,9-diethyl-fluoren-2-amine 
• 1370605-06-3 N,N-Di[4-(4-aminophenoxy)phenyl]-7-(benzothiazol-2-yl)-9,9-diethyl-fluoren-2-amine 
• 1372550-62-3 9,9-diethyl-N₂,N₇-diphenyl-N₂,N₇-di(pyren-1-yl)-9H-fluorene-2,7-diamine 

Relevant academic research and scientific papers

Electroluminescent properties of novel fluorene derivatives with aromatic amine moieties

2,7-Bis[(4-diphenylamino)phenylvinylene]-9,9-diethylfluorene(BDPDF, 1) and 2,7-bis[(9-ethyl-3-carbazolylvinylene)-9,9-diethylfluorene(BECDF, 2) have been synthesized and characterized. To evaluate electroluminescent performance, compound 1 and 2 were used

Synthesis, characterization and photo physical-theoretical analysis of D-π-A compounds. 2. Chain length effect through even-odd effect on the photophysical properties

In the continuous search for new compounds for solar devices, the family of dipolar D-π-A molecules, which have a donor (D) and an acceptor (A) charge joined by a conjugate bridge, have been the focus of attention in the recent years due their different properties. As we have shown before, there is a connection between the geometry of molecules based on tertiary asymmetric amines and their quantum yield. In the current work, four new compounds based on the same backbone molecule ((E)-2-cyano-3-(5-((E)-2-(9,9-diethyl-7-(phenylamino)-9H-fluoren-2-yl)vinyl)thiophen-2-yl)acrylic acid), but with different substituent, were synthesized. It is shown that the chain-size of the substituent group modifies the quantum yield. The news substituents introduced are a propyl (M8-3), butyl (M8-4), pentyl (M8-5) or hexyl (M8-6) group. In general, it was possible to see that the new substituents were able to increase their performances. Furthermore, an odd-even substituent effect, between propyl/pentyl and butyl/hexyl, was found and the theoretical geometrical data was able to follow the trend. However, theoretically, this substituent effect was inverted in the case of M8-3 and M8-4, which may be due to the disappearance in the emission patterns of an excited state close to 450 nm (at λ2), as it was shown in the experimental data. The most suitable behaviour belongs to [(E)-2-cyano-3-(5-((E)-2-(9,9-diethyl-7-(phenyl(propyl)amino)-9H-fluoren-2-yl)vinyl)thiophen-2-yl)acrylic acid] (M8-3). M8-3 has the highest quantum yields on average in all studied solvents; even higher than the last reported compounds with methyl (M8-1) and ethyl (M8-2) groups. Theoretically, the most likely explanation is that the dihedral angle formed between the carbonyl acceptor and nitrogen electron donor (Aryl-CO), should be as small as the molecule M8-3. This isolated compound has an average quantum yield including all solvents of 58.1% (average value), showing that a long group is not necessary to improve the performance.

Fluorenes substituted with fluorophenyl, difluorophenyl or trifluorophenyl fragments as materials for organic light emitting diodes

9,9-Diethylfluorenes substituted with two fluorophenyl, difluorophenyl or trifluorophenyl fragments were synthesized by the multi-step synthetic rout. The materials were characterized by 1H NMR spectroscopy, mass spectrometry, differential scanning calorimetry and thermogravimetric analyses. Some of the electro-active derivatives could form thin amorphous films and were tested as solution processed hole transporting layers in organic light- emitting diodes with Alq3 as the emitter and electron transporting material. Some of the electroluminescent devices demonstrated turn voltage of 5.5?V, a maximal photometric efficiency of about 1.0 cd/A and maximum brightness exceeding 960 cd/m2 .

Synthesis and Photophysical Properties of Laterally Asymmetric Digold(I) Alkynyls and Triazolyl: Ancillary Ligand and Organic Functionality Dictate Excited-State Dynamics

Four new laterally asymmetric dinuclear gold(I) complexes made from a new chromophoric ligand (Au-DiBTF0-3) have been characterized. Changing the organic ancillary ligand from a phosphine ((Au-DiBTF0 (PMe3) and Au-DiBTF1 (PCy3)) to an N-heterocyclic carbene (Au-DiBTF2) with an alkynyl linking moiety or modifying the alkynyl linkage to a triazolyl moiety with the ancillary ligand being an N-heterocyclic carbene (Au-DiBTF3) impacts the ground- and excited-state properties of these systems. All four complexes exhibit structured absorption and emission spectra with weak phosphorescence. A bathochromic shift is observed in both the ground-state absorption and luminescence spectra as the series varies from Au-DiBTF0 to Au-DiBTF3. The dinuclear alkynyl complexes (Au-DiBTF0-2) display decreased fluorescence lifetimes and fluorescence quantum yields along with more efficient intersystem crossing when the capping ligand is changed from a trialkylphosphine to an N-heterocyclic carbene. This change results in comparable rates of radiative decay and intersystem crossing and negligible rates of nonradiative decay. Changing the π-bridging moiety (Au-DiBTF3) results in a diminished fluorescence quantum yield, shorter fluorescence lifetime, and increased intersystem quantum yield, resulting in faster intersystem crossing accompanied by slower radiative decay and more efficient nonradiative decay relative to the alkynyl-bridged complexes. Density functional theory calculations are in accord with the observed photophysics, with nearly identical S1-to-T2 energy gaps for the dinuclear alkynyl complexes (Au-DiBTF0 and -2) and a smaller energy gap for Au-DiBTF3. Experimentally, Au-DiBTF3 has the highest rate constant and quantum yield of intersystem crossing of the new gold(I) organometallics.

Synthesis, characterization and photophysical-theoretical analysis of compounds A-π-D. 1. Effect of alkyl-phenyl substituted amines in photophysical properties

The study of new dipolar A-π-D molecules, which have an acceptor (A) and donor (D) charge joined by a conjugate bridge, have been an attention focus in the recent years due their different properties. In the current work, a molecular system has been modified in order to compare the effect on properties, such as quantum yield. Thus, two series were generated (alkyl- and alkoxy-substituted) to determine if molecules with tertiary asymmetric amines change their optical properties and whether quantum yield is affected. The different products have been characterized by several techniques such as UV–Vis spectrophotometry, elemental analysis, NMR, FT-IR, mass spectroscopy and fluorescence spectroscopy. Furthermore, their behavior in eight organic solvents, dichloromethane, tetrahydrofuran, ethyl acetate, 1,4-dioxane, acetone, acetonitrile, dimethylformamide and dimethylsulfoxide were experimentally and theoretically studied. The quantum yields were higher for the alkyl-substituted series. Theoretically, the dihedral angles formed between the tertiary amine and carbonyl group moieties have a correlation with quantum yield values, helping to explain why they are higher in non-polar solvents. Consequently, the maximum quantum yield was obtained with (E)-2-cyano-3-(5-((E)-2-(9,9-diethyl-7-(methyl(phenyl)amino)-9H-fluoren-2-yl) vinyl)thiophen-2-yl)acrylic acid (M8-1) in 1,4-dioxane, reaching 98.8%.

Fluorescent sensor of fluorene derivatives having phosphonic acid as a fluorogenic ionophore: Synthesis and static quenched properties for Fe(III)

A series of novel fluorene derivatives containing -PO(OH)2 (1, 2), -HS (3), and -N+ (CH3)3 (4) were synthesized and only phosphonic-functionalized fluorene derivatives can detect Fe3+ with high selectivity over other metal ions. The fluorescence quenching of 1 and 2 with titration Fe3+ in water-DMF solution fits the Perrin model of static quenching. Spectral analysis showed that Fe3+ bound with fluorene-based chemosensor through the O-atoms at the phosphonic group to form nonfluorescent complexes. The binding ratio was estimated by the Job plot and the trace levels of iron in samples were successfully monitored.

[4]Cyclofluorene: Unexpected Influence of Alkyl Chain Length

Presented here is the study of a new example of [4]cyclofluorene, with ethyl chains on the bridgeheads. Its molecular structure was established by solution NMR spectroscopy and single-crystal X-ray diffraction. Three successive oxidation processes and one reversible reduction were observed through cyclic voltammetry. The optical properties were characterized both in solution and thin film by UV/visible spectroscopy as well as stationary and time-resolved fluorescence. It was found that this [4]cyclofluorene displays different characteristics compared with the other [4]cyclofluorenes substituted by methyl or propyl chains: a simple modification of the chain length induces a non-negligible effect on the emission properties, which must be linked to the specific arrangement of the fluorene units. Furthermore, single-crystal X-ray diffraction reveals the formation of a pseudo-tubular solid-state arrangement of fully symmetrical ring structures, which was not observed for the other members of the [4]cyclofluorenes family. This finding could open the way to modulation of properties of cyclofluorenes through alkyl chain engineering.

Electron Transfer around a Molecular Corner

The distance dependence of electron transfer (ET) is commonly investigated in linear rigid rod-like compounds, but studies of molecular wires with integrated corners imposing 90° angles are very rare. By using spirobifluorene as a key bridging element and by substituting it at different positions, two isomeric series of donor-bridge-acceptor compounds with either nearly linear or angled geometries were obtained. Photoinduced ET in both series is dominated by rapid through-bond hole hopping across oligofluorene bridges over distances of up to 70 ?. Despite considerable conformational flexibility, direct through-space and through-solvent ET is negligible even in the angled series. The independence of the ET rate constant on the total number of fluorene units in the angled series is attributed to a rate-limiting tunneling step through the spirobifluorene corner. This finding is relevant for multidimensional ET systems and grids in which individual molecular wires are interlinked at 90° angles.

Fluorene bridged cyclic N-heterocyclic carbene silver complex as well as preparation method and application thereof

The invention discloses a cyclic N-heterocyclic carbene silver complex as well as a preparation method and application thereof. The preparation method comprises the steps of enabling fluorine, used asa raw material, to react with liquid bromine, and enabling the obtained product (W) to react with bromoethane so as to obtain a product (X); enabling the product (X) to react with imidazole so as toobtain a compound (Y), enabling the compound (Y) to further react with benzyl bromide so as to obtain a product (Z), and enabling the product (Z) to react with silver oxide so as to obtain the cyclicN-heterocyclic carbene silver complex (1). The cyclic N-heterocyclic carbene silver complex (1) is used as the main body, different types of nitrates are taken as the objects, and the main body and objects are separately dissolved in an organic solvent at the temperature of 25 DEG C or below; the main body solution is separately mixed with the different object solutions under a certain concentration, and the fluorescence spectrums of the mixed solutions are measured, so that the objects which can be identified by the main body can be found; titration is carried out on the main body by using the objects which can be identified by the main body and have the different concentrations, so that the fluorescence spectrum is determined. The cyclic N-heterocyclic carbene silver complex prepared bythe method has the advantages of being simple to prepare and obvious in fluorescent and light-sensitive effects, and can be used for making a fluorescent molecular recognition system, thus being expected to be applied to the field of fluorescent chemistry.

Two-photon absorbing compounds and methods of making same

A two-photon absorbing (TPA) compound is provided, along with a method of making same. The TPA compound has a general structural formula: where A is an acceptor moiety that is connected to m number of diarylaminofluorene arms (m=1-3); in each diarylaminofluorene arms, R is selected from linear or branched alkyl chains having a general formula CnH2n+1, where n is in a range from 2 to 25; where R1, R2, and R3 are independently selected from H or C1-C4 alkyls; where R4 is selected from C1-C5 alkyls; and wherein R5 through R10 are independently selected from H, alkoxyls, alkyls, or aryls. A may be benzothiazol-2-yl, benzo[1,2-d:4,5-d′]bisthiazole-2,6-diyl, thiazolo[5,4-d]thiazole-2,5-diyl-, 1,3,5-triazine-2,4,6-triyl, 1,3,5-triazine-2,4,6-triyl, benzo[1,2-d:3,4-d′:5,6-d″]tristhiazole-2,5,8-triyl-, or dithieno[3,2-b:2′,3′-d]thiophene-2,6-diyl-.