[2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene
6,6'-diphenylfulvene
CAS: 2175-90-8
Molecular Formula: C18H14
[2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene - Names and Identifiers
| Name | 6,6'-diphenylfulvene |
| Synonyms | DIPHENYLFULVENE 6,6-DIPHENYLFULVENE 6,6'-diphenylfulvene 6,6'-DIPHENYLFULVENE Fulvene, 6,6-diphenyl Diphenylmethylidene cyclopentadiene 5-(DIPHENYLMETHYLENE)-1,3-CYCLOPENTADIENE Methane, 2,4-cyclopentadien-1-ylidenediphenyl- [2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene |
| CAS | 2175-90-8 |
| EINECS | 218-533-4 |
| InChI | InChI=1/C18H14/c1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16/h1-14H |
[2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene - Physico-chemical Properties
| Molecular Formula | C18H14 |
| Molar Mass | 230.3 |
| Density | 1.0829 (estimate) |
| Melting Point | 81.5-83 °C (lit.) |
| Boling Point | 307.3°C (rough estimate) |
| Flash Point | 204.1°C |
| Vapor Presure | 0.033-0.084Pa at 25℃ |
| Appearance | Solid |
| Color | Light yellow to Brown |
| Storage Condition | Refrigerator |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00001419 |
[2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene - Risk and Safety
| WGK Germany | 3 |
[2,4-Cyclopentadien-1-ylidene(phenyl)methyl]benzene - Reference Information
| LogP | 3.43 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | under mild conditions and hydrogen atmosphere, the low-valent chin catalytic system composed of Cp2TiCl2 and i-rPMgBr not only has good hydrogenation activity for 1,5 cyclooctadiene, but also can isomerize olefins. The catalyst can not only linear isomerize 1,5 monohexadiene, but also cyclization isomerization. In this paper, under mild conditions and hydrogen atmosphere, the hydrogenation reaction of the low-priced catalyst composed of Cp2TiCl2 and i-rPMg-Br to the conjugated polyene of 6,6 diphenyl fulene is studied, which can partially hydrogenate the polyolefin and also isomerize part of the hydrogenation product. The final product always retains the double bond and is not easy to further hydrogenate into substituted cyclopentane, and no linear isomerization occurs in the reaction. |
| Synthesis route | There is obviously a velocity gradient during the hydrogenation reaction. At the beginning, the hydrogen absorption rate was faster, and then the speed slowed down significantly. This is similar to the hydrogenation reaction under tP and Pd catalysis. When the hydrogen absorption rate is just beginning to slow down, water is added to quench the reaction, and the product of 1 molecule of hydrogen added to the ring double bond is separated to replace cyclopentadiene (A). This shows that the hydrogenation activity of the external double bond is higher than that of the internal double bond. Fig. 2 shows step 1 of the 6, 6-diphenylfulene synthesis route. The second molecule of hydrogen can be added to the double bond far from the substituent in the ring of (A), but the reaction speed is slow, forming substituted cyclopentene (B). (B) The inner double bond is shifted to the outer ring to form the isomer (C). Prolonging the reaction time and appropriately increasing the amount of catalyst do not lead to the formation of substituted cyclopentanes, which indicates that substituted cyclopentenes (B) and (C) are not easy to be further hydrogenated under these conditions. This is consistent with the literature results. Figure 3 shows the 6, 6-diphenylfulene synthesis route step 2. the 1H NMR spectrum of the final product shows that the relative molar ratio of (a), (B) and (c) in equilibrium is 14:64:23. under the experimental conditions in this paper, the phenyl group of 6,6 diphenylfulene does not undergo hydrogenation. |
| UV absorption effect | The study of the quantitative relationship between the structure and properties of organic compound molecules has important theoretical significance and practical value, and has received extensive attention. The electronic absorption spectra of organic conjugated systems are not only closely related to the molecular structure, but also affected by the chemical environment. As far as the ultraviolet absorption energy of dibenzo-rich compounds is concerned, it is mainly affected by two factors: one is the internal structure of the molecule, that is, the nature of the substituent; the other is the external environment of the molecule, that is, the molecule The surrounding medium, such as solvent, etc. For the solvent effect on the ultraviolet absorption of organic matter, there have been a lot of studies. The results show that in different solvents, some absorption wavelengths have a red shift, and some absorption wavelengths have a blue shift. The direction of movement is related to the ground state of the solute molecule. The dipole moment state of the excited state is related, but the size and direction of its movement cannot be accurately predicted theoretically. At the same time, there are many polar parameters that can express solvents. However, whether these parameters can be used to quantitatively study the variation of ultraviolet absorption energy of dibenzo-rich compounds in different solvents. In fact, the molecules of dibenzo-rich compounds will have solute-solvent interactions in solvents, and the size of this interaction is also different in different solvents. The experimental results show that even the UV absorption energy of the same solute molecule in different solvents will change. For example, p-DPFOMe the absorption wavelength difference between THF and chlorobenzene is more than 17 nm, the solvent effect is very obvious. Therefore, if we want to investigate the common law of UV absorption energy changes of dibenzo-rich ene molecules in various solvents, we must consider the solvent effect. |
| References | [1] Wei Baiying. Study on Influencing Factors of Spectral Properties of Dibenzofulene and Aryl Schiff Base [D]. Hunan University of Science and Technology, 2014. [2] Wang Jiaxi, He Zhengjie, Chen Shoushan, Wang Xukun, Wang Honggen. Reaction of Lithium Diphenylphosphinyl with Fulene-Synthesis and Characterization of Substituted Ferrocene Derivatives [J]. Journal of Chemistry of Colleges and Universities, 1994,(06):854-858. [3] He Zhengjie, Chen Shoushan. 6, hydrogenation of 6-diphenylfulene under Cp_2TiCl_2-i-prMgBr Catalysis [J]. Journal of Chemistry of Colleges and Universities, 1994,(05):703-704. |
Last Update：2024-04-09 21:11:58
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