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Matthias Tacke - One of the best experts on this subject based on the ideXlab platform.
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bioorganometallic Fulvene derived titanocene anti cancer drugs
Chemical Society Reviews, 2008Co-Authors: Katja Strohfeldt, Matthias TackeAbstract:6-Substituted Fulvenes are interesting and easily accessible starting materials for the synthesis of novel substituted titanocenes via reductive dimerisation, carbolithiation or hydridolithiation reactions, which are followed by a transmetallation reaction with titanium tetrachloride in the latter two cases. Depending on the substitution pattern, these titanocenes prove to be bioorganometallic anti-cancer drugs, which have significant potential against advanced or metastatic renal-cell cancer. Patients bearing these stages of kidney cancer have a poor prognosis so far and therefore real progress in the area of metal-based anti-cancer drugs may come from this simple and effective synthetic approach. This tutorial review provides an insight into the synthesis of Fulvene-derived titanocenes and their activity in preclinical experiments.
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Synthesis and cytotoxicity studies of methoxy benzyl substituted titanocenes
Journal of Organometallic Chemistry, 2008Co-Authors: James Claffey, Clara Pampillón, Megan Hogan, Helge Müller-bunz, Matthias TackeAbstract:Abstract From the reaction of 6(2-methoxy-phenyl)Fulvene ( 1a ), 6(3-methoxy-phenyl)Fulvene ( 1b ), 6(3,4-dimethoxy-phenyl)Fulvene ( 1c ) and 6(3,4,5-trimethoxy-phenyl)Fulvene ( 1d ) with LiBEt 3 H, lithiated cyclopentadienide intermediates 2a – d were synthesised. These intermediates were then transmetallated to titanium with TiCl 4 to give benzyl substituted titanocenes bis-[(2-methoxy-benzyl)cyclopentadienyl]titanium(IV) dichloride ( 3a ), bis-[(3-methoxy-benzyl)cyclopentadienyl]titanium(IV) dichloride ( 3b ), bis-[(3,4-dimethoxy-benzyl)cyclopentadienyl]titanium(IV) dichloride ( 3c ) and bis-[(3,4,5-trimethoxy-benzyl)cyclopentadienyl]titanium(IV) dichloride ( 3d ). The three titanocenes 3a – c were characterised by single crystal X-ray diffraction, while the structure of the fourth titanocene 3d was elucidated through a DFT calculation. All four titanocenes had their cytotoxicity investigated through preliminary in vitro testing on the LLC-PK (pig kidney epithelial) cell line in order to determine their IC 50 values. Titanocenes 3a – d were found to have IC 50 values of 97, 159, 88 and 253 μM, respectively. All four titanocene derivatives show significant cytotoxicity improvement when compared to unsubstituted titanocene dichloride.
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Proliferative and antiproliferative effects in substituted titanocene anticancer drugs
Transition Metal Chemistry, 2007Co-Authors: Katja Strohfeldt, Clara Pampillón, Helge Müller-bunz, Matthias TackeAbstract:Substituted titanocenes like ansa-titanocenes, diarylmethyl-substituted and benzyl-substituted titanocenes, are known for their cytotoxic potential and they can be synthesised using 6-arylFulvenes. Nevertheless, in the case of using 6-(4-morpholin-4yl-phenyl) Fulvene (5a) or 6-{[ bis -(2-methoxyethyl)amino]phenyl} Fulvene (5b) the synthetic possibilities seem to be limited, but the morpholino and the bis -(2-methoxyethyl)amino substituent are in terms of an improved water solubility and drug availability in the cell very interesting groups. The corresponding benzaldehydes, which are the starting material for the synthesis of these Fulvenes, were not commercially available and therefore, a modified synthetic approach had to be introduced. Nevertheless, the reactivity of the obtained Fulvenes was unexpected and only the ansa-titanocene bis -[{[ bis -(2-methoxyethyl)amino]phenyl}cyclopentadienyl] titanium(IV) dichloride (6b) and the benzyl-substituted titanocene [1,2-di(cyclopentadienyl)-1,2-di(4-morpholin-4yl-phenyl)-ethanediyl] titanium dichloride (8a) could be obtained and characterised. When the benzyl-substituted titanocene (8a) was tested against pig kidney cells (LLC-PK) an anti-proliferative effect, resulting in an IC_50 value of 25 µM, was observed. This IC_50 value is in the lower range of the cytotoxicities evaluated for titanocenes up to now. The ansa-titanocene (6b) showed surprisingly, when tested on the same cell line, a proliferative effect.
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Proliferative and antiproliferative effects in substituted titanocene anticancer drugs
Transition Metal Chemistry, 2007Co-Authors: Katja Strohfeldt, Clara Pampillón, Helge Müller-bunz, Matthias TackeAbstract:Substituted titanocenes like ansa-titanocenes, diarylmethyl-substituted and benzyl-substituted titanocenes, are known for their cytotoxic potential and they can be synthesised using 6-arylFulvenes. Nevertheless, in the case of using 6-(4-morpholin-4yl-phenyl) Fulvene (5a) or 6-{[bis-(2-methoxyethyl)amino]phenyl} Fulvene (5b) the synthetic possibilities seem to be limited, but the morpholino and the bis-(2-methoxyethyl)amino substituent are in terms of an improved water solubility and drug availability in the cell very interesting groups. The corresponding benzaldehydes, which are the starting material for the synthesis of these Fulvenes, were not commercially available and therefore, a modified synthetic approach had to be introduced. Nevertheless, the reactivity of the obtained Fulvenes was unexpected and only the ansa-titanocene bis-[{[bis-(2-methoxyethyl)amino]phenyl}cyclopentadienyl] titanium(IV) dichloride (6b) and the benzyl-substituted titanocene [1,2-di(cyclopentadienyl)-1,2-di(4-morpholin-4yl-phenyl)-ethanediyl] titanium dichloride (8a) could be obtained and characterised.
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Structures of 6-(substituted-phenyl)Fulvenes
Zeitschrift für Kristallographie, 2007Co-Authors: Helge Müller-bunz, Katja Strohfeldt, Clara Pampillón, Nigel J. Sweeney, James Claffey, Ina Dix, Ying Lou, Matthias TackeAbstract:The syntheses and crystal structures of a series of 6-(substituted-phenyl) Fulvenes are reported. In three instances the molecular structures determined by X-Ray crystallography were compared to the results of DFT calculations. In these cases only minor differences were found between the optimised DFT calculation and the molecule found in the crystal structure. This is of particular interest in the case of 6-(p-[N-acetyl]aminophenyl)Fulvene which shows intermolecular hydrogen bonding.
Katja Strohfeldt - One of the best experts on this subject based on the ideXlab platform.
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bioorganometallic Fulvene derived titanocene anti cancer drugs
Chemical Society Reviews, 2008Co-Authors: Katja Strohfeldt, Matthias TackeAbstract:6-Substituted Fulvenes are interesting and easily accessible starting materials for the synthesis of novel substituted titanocenes via reductive dimerisation, carbolithiation or hydridolithiation reactions, which are followed by a transmetallation reaction with titanium tetrachloride in the latter two cases. Depending on the substitution pattern, these titanocenes prove to be bioorganometallic anti-cancer drugs, which have significant potential against advanced or metastatic renal-cell cancer. Patients bearing these stages of kidney cancer have a poor prognosis so far and therefore real progress in the area of metal-based anti-cancer drugs may come from this simple and effective synthetic approach. This tutorial review provides an insight into the synthesis of Fulvene-derived titanocenes and their activity in preclinical experiments.
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Proliferative and antiproliferative effects in substituted titanocene anticancer drugs
Transition Metal Chemistry, 2007Co-Authors: Katja Strohfeldt, Clara Pampillón, Helge Müller-bunz, Matthias TackeAbstract:Substituted titanocenes like ansa-titanocenes, diarylmethyl-substituted and benzyl-substituted titanocenes, are known for their cytotoxic potential and they can be synthesised using 6-arylFulvenes. Nevertheless, in the case of using 6-(4-morpholin-4yl-phenyl) Fulvene (5a) or 6-{[ bis -(2-methoxyethyl)amino]phenyl} Fulvene (5b) the synthetic possibilities seem to be limited, but the morpholino and the bis -(2-methoxyethyl)amino substituent are in terms of an improved water solubility and drug availability in the cell very interesting groups. The corresponding benzaldehydes, which are the starting material for the synthesis of these Fulvenes, were not commercially available and therefore, a modified synthetic approach had to be introduced. Nevertheless, the reactivity of the obtained Fulvenes was unexpected and only the ansa-titanocene bis -[{[ bis -(2-methoxyethyl)amino]phenyl}cyclopentadienyl] titanium(IV) dichloride (6b) and the benzyl-substituted titanocene [1,2-di(cyclopentadienyl)-1,2-di(4-morpholin-4yl-phenyl)-ethanediyl] titanium dichloride (8a) could be obtained and characterised. When the benzyl-substituted titanocene (8a) was tested against pig kidney cells (LLC-PK) an anti-proliferative effect, resulting in an IC_50 value of 25 µM, was observed. This IC_50 value is in the lower range of the cytotoxicities evaluated for titanocenes up to now. The ansa-titanocene (6b) showed surprisingly, when tested on the same cell line, a proliferative effect.
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Proliferative and antiproliferative effects in substituted titanocene anticancer drugs
Transition Metal Chemistry, 2007Co-Authors: Katja Strohfeldt, Clara Pampillón, Helge Müller-bunz, Matthias TackeAbstract:Substituted titanocenes like ansa-titanocenes, diarylmethyl-substituted and benzyl-substituted titanocenes, are known for their cytotoxic potential and they can be synthesised using 6-arylFulvenes. Nevertheless, in the case of using 6-(4-morpholin-4yl-phenyl) Fulvene (5a) or 6-{[bis-(2-methoxyethyl)amino]phenyl} Fulvene (5b) the synthetic possibilities seem to be limited, but the morpholino and the bis-(2-methoxyethyl)amino substituent are in terms of an improved water solubility and drug availability in the cell very interesting groups. The corresponding benzaldehydes, which are the starting material for the synthesis of these Fulvenes, were not commercially available and therefore, a modified synthetic approach had to be introduced. Nevertheless, the reactivity of the obtained Fulvenes was unexpected and only the ansa-titanocene bis-[{[bis-(2-methoxyethyl)amino]phenyl}cyclopentadienyl] titanium(IV) dichloride (6b) and the benzyl-substituted titanocene [1,2-di(cyclopentadienyl)-1,2-di(4-morpholin-4yl-phenyl)-ethanediyl] titanium dichloride (8a) could be obtained and characterised.
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Structures of 6-(substituted-phenyl)Fulvenes
Zeitschrift für Kristallographie, 2007Co-Authors: Helge Müller-bunz, Katja Strohfeldt, Clara Pampillón, Nigel J. Sweeney, James Claffey, Ina Dix, Ying Lou, Matthias TackeAbstract:The syntheses and crystal structures of a series of 6-(substituted-phenyl) Fulvenes are reported. In three instances the molecular structures determined by X-Ray crystallography were compared to the results of DFT calculations. In these cases only minor differences were found between the optimised DFT calculation and the molecule found in the crystal structure. This is of particular interest in the case of 6-(p-[N-acetyl]aminophenyl)Fulvene which shows intermolecular hydrogen bonding.
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Glycol Methyl Ether and Glycol Amine Substituted Titanocenes as Antitumor Agents
European Journal of Inorganic Chemistry, 2006Co-Authors: Katja Strohfeldt, Clara Pampillón, Nigel J. Sweeney, Helge Müller-bunz, Matthias TackeAbstract:6-[4-(2-Methoxyethoxy)phenyl]Fulvene (3a) and 6-{4-[2-(dimethylamino)ethoxy]phenyl}Fulvene (3b) were prepared as the starting materials for the synthesis of three different classes of titanocenes, which are ansa-titanocenes, diarylmethyl-substituted titanocenes and benzyl-substituted titanocenes. Because the synthetic possibilities seem to be limited, only ansa-titanocene {1,2-bis(cyclopentadienyl)-1,2-bis[4-(2-methoxyethoxy)phenyl]ethanediyl}titanium dichloride (4a) and benzyl-substituted titanocene bis-{[4-(2-methoxyethoxy)benzyl]cyclopentadienyl}titanium(IV) dichloride (6a) were obtained and characterised. The change in the substitution pattern of the phenyl moiety from an oxygen atom to a nitrogen atom had such a big influence on the reaction that not one compound of the three titanocene classes could be synthesised, and it was also not possible to obtain diarylmethyl-substituted titanocenes with the use of either of the Fulvenes. When benzyl-substituted titanocene 6a was tested against pig kidney cells (LLC-PK), an antiproliferative effect that results in an IC50 value of 43 μM, was observed. This IC50 value is in the lower range of the cytotoxicities evaluated for titanocenes up to now. ansa-Titanocene 4a surprisingly showed, when tested on the same cell line, a proliferative effect together with a fast rate of hydrolysis. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Gary J. Balaich - One of the best experts on this subject based on the ideXlab platform.
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correlation of structure with crystalline to amorphous phase transitions of 1 3 6 substituted Fulvene derived molecular glasses
Journal of Organic Chemistry, 2020Co-Authors: Loren C Brown, Gary J. Balaich, Andrew J. Peloquin, Nicholas P Godman, Scott T. IaconoAbstract:An investigation into the crystalline to amorphous phase transitions of prepared 1,3,6-substituted pentaFulvenes showed the expected reversible heated melt and cooling recrystallization in only a few examples. Systematic incorporation of bulky substituents at the 6-position of the Fulvene ring led to the nonreversible thermal behavior, rendering phases that were locked into glassy, vitrified states. These molecular glasses produced physically translucent and amorphous features with glass transition temperatures in the range of 61-77 °C, comparable with high-strength plastics such as polyethylene terephthalate. Additionally, the melting point transitions and the resulting heat of fusion values were found to be directly influenced by the nature of the 6-position substituent. Single crystal X-ray crystallography showed that in some cases, Fulvenes possessing fused aromatics exhibited a high degree of intermolecular π-π stacking. These results point to a class of molecular glass formers as host materials possessing tunable bulk properties for potentially new optical applications.
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Crystal structures of a series of 6-aryl-1,3-diphenyl-Fulvenes.
Acta Crystallographica Section E Crystallographic Communications, 2019Co-Authors: Andrew J. Peloquin, Scott T. Iacono, Sonya K. Adas, Gary J. BalaichAbstract:The synthesis and crystal structures of a series of 6-arylfuvlenes (Fulvene is 5-methylidenecyclopenta-1,3-diene) with varying methylation patterns on the 6-phenyl substituent are reported, namely 6-(3-methylphenyl)-1,3-diphenylFulvene (C25H20), 6-(4-methylphenyl)-1,3-diphenylFulvene (C25H20), 6-mesityl-3-diphenylFulvene (C27H24) and 6-(2,3,4,5,6-pentamethylphenyl)-1,3-diphenylFulvene (C29H28). The bond lengths are typical of those observed in related Fulvenes. A network of C—H⋯π ring interactions consolidates the packing in each structure.
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Coordination complexes of chromium(0) with a series of 1,3-diphenyl-6-aryl-Fulvenes.
Acta crystallographica. Section E Crystallographic communications, 2018Co-Authors: Andrew J. Peloquin, Gary J. Balaich, Madelyn B Smith, Bryce J O'connell, Kamran B Ghiassi, Scott T. IaconoAbstract:The synthesis and structural properties of a series of chromium tricarbonyl 'piano-stool' complexes bearing substituted penta-Fulvene ligands were studied. The complexes, tricarbon-yl(1,3,6-tri-phenyl-Fulvene)chromium(0) benz-ene hemisolvate, [Cr(C24H18)(CO)3]·0.5C6H6 (I), tricarbon-yl[1,3-di-phen-yl-6-(3-vinyl-phen-yl)Fulvene]chromium(0), [Cr(C26H20)(CO)3] (II), and tricarbon-yl[1,3-diphenyl-6-(pyren-1-yl)Fulvene]chromium(0), [Cr(C34H22)(CO)3] (III), each have a distorted octa-hedral geometry, with the Fulvene coordinated in a π-η2:π-η2:π-η2 fashion. Significant deviation of the exocyclic Fulvene double bond from the cyclo-penta-diene plane accompanies coordination. Evidence of non-covalent π-π inter-actions was observed in both (I) and (III), with centroid-to-centroid distances ranging from 3.330 (8) to 3.494 (8) Å.
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Synthesis of reactive 1,3-diphenyl-6-aryl-substituted Fulvene chromophores.
Data in brief, 2018Co-Authors: Stephen M. Budy, David Y. Son, Gary J. Balaich, Scott T. IaconoAbstract:Abstract This data article describes a detailed synthetic strategy and experimental data for the synthesis of brominated Fulvene chromophores as reactive precursors/monomers for conjugated organic materials. Metal-mediated coupling reactions of brominated Fulvenes would result in conjugated small molecules or polymers that would find application as organic light emitting diodes (OLEDs) and photovoltaic (PV) applications.
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Coordination complexes of chromium(0) with a series of 1,3-diphenyl-6-arylFulvenes
International Union of Crystallography, 2018Co-Authors: Andrew J. Peloquin, Gary J. Balaich, Madelyn B Smith, Bryce J O'connell, Kamran B Ghiassi, Scott T. IaconoAbstract:The synthesis and structural properties of a series of chromium tricarbonyl `piano-stool' complexes bearing substituted pentaFulvene ligands were studied. The complexes, tricarbonyl(1,3,6-triphenylFulvene)chromium(0) benzene hemisolvate, [Cr(C24H18)(CO)3]·0.5C6H6 (I), tricarbonyl[1,3-diphenyl-6-(3-vinylphenyl)Fulvene]chromium(0), [Cr(C26H20)(CO)3] (II), and tricarbonyl[1,3-diphenyl-6-(pyren-1-yl)Fulvene]chromium(0), [Cr(C34H22)(CO)3] (III), each have a distorted octahedral geometry, with the Fulvene coordinated in a π–η2:π–η2:π–η2 fashion. Significant deviation of the exocyclic Fulvene double bond from the cyclopentadiene plane accompanies coordination. Evidence of non-covalent π–π interactions was observed in both (I) and (III), with centroid-to-centroid distances ranging from 3.330 (8) to 3.494 (8) Å
Scott T. Iacono - One of the best experts on this subject based on the ideXlab platform.
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Density Functional Theory Investigation of Fulvene-Derivatized Fullerenes as Candidates for Organic Solar Cells.
The journal of physical chemistry. A, 2020Co-Authors: Tim Fuhrer, Jordan Snelgrove, Cynthia A. Corley, Scott T. IaconoAbstract:Interest within the scientific community in organic solar cells has been on the rise over the last two decades as researchers respond to increasing demands for alternative renewable energy sources. Fulvene, fullerene, and endohedral metallofullerene derivatives have individually shown great promise as efficient charge transfer agents. Despite the heavy demand for research in this area, there have been no studies reported to date that explore the electronic behavior of molecules containing both fullerene and Fulvene groups. The lack of interest may be attributed to inherent limitations and inaccuracy in most density functional theory (DFT) band gap calculations for large molecules. Herein we present a systematic computational investigation of the band gaps and dipole moments of several test fullerene-Fulvene molecules using a novel DFT method that has been modified to allow accurate computation of the band gaps of this class of molecules. Calculated results showed promising low band gap energies and attractive conductive properties for all fullerene-Fulvene derivatives. This new DFT method can conceivably be an invaluable tool that can provide predictive insight into the suitability of similar high molecular weight materials for application in organic solar cell devices.
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correlation of structure with crystalline to amorphous phase transitions of 1 3 6 substituted Fulvene derived molecular glasses
Journal of Organic Chemistry, 2020Co-Authors: Loren C Brown, Gary J. Balaich, Andrew J. Peloquin, Nicholas P Godman, Scott T. IaconoAbstract:An investigation into the crystalline to amorphous phase transitions of prepared 1,3,6-substituted pentaFulvenes showed the expected reversible heated melt and cooling recrystallization in only a few examples. Systematic incorporation of bulky substituents at the 6-position of the Fulvene ring led to the nonreversible thermal behavior, rendering phases that were locked into glassy, vitrified states. These molecular glasses produced physically translucent and amorphous features with glass transition temperatures in the range of 61-77 °C, comparable with high-strength plastics such as polyethylene terephthalate. Additionally, the melting point transitions and the resulting heat of fusion values were found to be directly influenced by the nature of the 6-position substituent. Single crystal X-ray crystallography showed that in some cases, Fulvenes possessing fused aromatics exhibited a high degree of intermolecular π-π stacking. These results point to a class of molecular glass formers as host materials possessing tunable bulk properties for potentially new optical applications.
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Crystal structures of a series of 6-aryl-1,3-diphenyl-Fulvenes.
Acta Crystallographica Section E Crystallographic Communications, 2019Co-Authors: Andrew J. Peloquin, Scott T. Iacono, Sonya K. Adas, Gary J. BalaichAbstract:The synthesis and crystal structures of a series of 6-arylfuvlenes (Fulvene is 5-methylidenecyclopenta-1,3-diene) with varying methylation patterns on the 6-phenyl substituent are reported, namely 6-(3-methylphenyl)-1,3-diphenylFulvene (C25H20), 6-(4-methylphenyl)-1,3-diphenylFulvene (C25H20), 6-mesityl-3-diphenylFulvene (C27H24) and 6-(2,3,4,5,6-pentamethylphenyl)-1,3-diphenylFulvene (C29H28). The bond lengths are typical of those observed in related Fulvenes. A network of C—H⋯π ring interactions consolidates the packing in each structure.
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Coordination complexes of chromium(0) with a series of 1,3-diphenyl-6-aryl-Fulvenes.
Acta crystallographica. Section E Crystallographic communications, 2018Co-Authors: Andrew J. Peloquin, Gary J. Balaich, Madelyn B Smith, Bryce J O'connell, Kamran B Ghiassi, Scott T. IaconoAbstract:The synthesis and structural properties of a series of chromium tricarbonyl 'piano-stool' complexes bearing substituted penta-Fulvene ligands were studied. The complexes, tricarbon-yl(1,3,6-tri-phenyl-Fulvene)chromium(0) benz-ene hemisolvate, [Cr(C24H18)(CO)3]·0.5C6H6 (I), tricarbon-yl[1,3-di-phen-yl-6-(3-vinyl-phen-yl)Fulvene]chromium(0), [Cr(C26H20)(CO)3] (II), and tricarbon-yl[1,3-diphenyl-6-(pyren-1-yl)Fulvene]chromium(0), [Cr(C34H22)(CO)3] (III), each have a distorted octa-hedral geometry, with the Fulvene coordinated in a π-η2:π-η2:π-η2 fashion. Significant deviation of the exocyclic Fulvene double bond from the cyclo-penta-diene plane accompanies coordination. Evidence of non-covalent π-π inter-actions was observed in both (I) and (III), with centroid-to-centroid distances ranging from 3.330 (8) to 3.494 (8) Å.
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Synthesis of reactive 1,3-diphenyl-6-aryl-substituted Fulvene chromophores.
Data in brief, 2018Co-Authors: Stephen M. Budy, David Y. Son, Gary J. Balaich, Scott T. IaconoAbstract:Abstract This data article describes a detailed synthetic strategy and experimental data for the synthesis of brominated Fulvene chromophores as reactive precursors/monomers for conjugated organic materials. Metal-mediated coupling reactions of brominated Fulvenes would result in conjugated small molecules or polymers that would find application as organic light emitting diodes (OLEDs) and photovoltaic (PV) applications.
Ru-qi Huang - One of the best experts on this subject based on the ideXlab platform.
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organometallic silver i coordination polymers and supramolecular complexes based on novel multidentate thiophene and benzenenitrile containing symmetric and unsymmetric Fulvene ligands
Organometallics, 2006Co-Authors: Yu-bin Dong, Yan Geng, Ru-qi HuangAbstract:Seven new conjugated symmetric and unsymmetric Fulvene ligands L1−L7 were synthesized. Thirteen new organometallic coordination polymers and supramolecular complexes were obtained through self-assembly based on these new Fulvene ligands in the benzene/toluene mixed solvent system. Compounds 1−13 have been fully characterized by infrared spectroscopy, elemental analysis, and single-crystal X-ray diffraction. The results indicate that the coordination chemistry of new Fulvene ligands is versatile. They can adopt either a cis or a trans conformation to bind Ag(I) ion through not only the terminal −CN and thiophene functional groups but also the Fulvene carbon atoms into organometallic coordination polymers or discrete complexes. In addition, the luminescent properties of L1, L3, L5, and L7 and some of their Ag(I) complexes were investigated preliminarily in EtOH and the solid state.
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New Ag(I) Organometallic Coordination Polymer and Co(II) Supramolecular Complex Generated from a New Type of Fulvene Ligand
Crystal Growth & Design, 2005Co-Authors: Peng Wang, Yu-bin Dong, Ru-qi Huang, Mark D. SmithAbstract:One novel Fulvene ligand HL was synthesized successfully by an aroylation reaction of substituted cyclopentadienyl anion. The coordination chemistry of Fulvene ligand HL is investigated. The study demonstrated that the Fulvene-type ligand HL could be used as multidentate or chelating ligand to coordinate transition metal ions into a coordination polymer or a supramolecular complex. One novel one-dimensional Ag(I)−Fulvene organometallic coordination polymer, namely, [Ag(HL)(H2O)]SbF6 (1) and one Co(II) complex, namely, Co(L)2·2C2H5OH (2), with an unusual seven-membered metallo-ring unit were synthesized successfully based on HL and L, respectively. In the solid state, complex 2 adopts a novel hydrogen bonded one-dimensional chain motif.
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syntheses and structures of ag i containing coordination polymers and co ii containing supramolecular complex based on novel Fulvene ligands
Inorganic Chemistry, 2004Co-Authors: Yu-bin Dong, Peng Wang, Ru-qi Huang, Mark D. SmithAbstract:Three new rigid conjugated Fulvene ligands L1−L3 were synthesized. L1 and L3 have been prepared by an aroylation reaction of cyclohexyl-substituted cyclopentadienyl anions. L2 was prepared by the reaction of L1 with PhNHNH2 in hot enthanol. Six new coordination polymers, namely [Ag(C25H20N2O2)(ClO4)]·3.5C6H6 (1), [Ag2(μ-C31H24N4)(η2-C6H6)(H2O)](ClO4)2·(C6H6)·(H2O)0.5 (3), [Ag(C31H24N4)]SbF6·solvate (4), [Ag(C31H24N4)](SbF6)2·2C6H6·CH2Cl2 (5), [Ag(C25H20N2O2)2]SbF6 (6), and [Ag(C25H20N2O2)2]SbF6 (7), and one seven-membered cobaltacycle-containing complex, namely Co(C25H20N2O2)2(C2H5OH)2 (2), were obtained through self-assembly based on these three new Fulvene lignads. L2−L3 and compounds 1−7 have been fully characterized by infrared spectroscopy, elemental analysis, and single-crystal X-ray diffraction. The results indicate that the coordination chemistry of new Fulvene ligands is versatile. They can bind metal ions not only through the terminal N-donors and Fulvene carbon atoms into organometallic coordin...
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new ag i inorganic organic coordination polymers and m ii m co ii and mn ii molecular complexes generated from a new type of Fulvene ligand
Dalton Transactions, 2003Co-Authors: Yu-bin Dong, Ru-qi Huang, Guoxia Jin, Mark D. SmithAbstract:One new Fulvene-type ligand 1 was synthesized successfully by aroylation reaction of substituted cyclopentadienyl anions. The coordination chemistry of Fulvene ligands 1 and 2 were investigated. The study demonstrated that these Fulvene-type ligands could be used as bidentate or chelating ligands to coordinate transition metal ions into coordination polymers or supramolecular complexes. Two novel one-dimensional Ag(I)–Fulvene coordination polymers, namely [Ag(1)2(PF6)]·C6H6 and [Ag(1)2(SbF6)]·2C7H8, consisting of an Ag2(ligand)2 unit and two M(II) (M = Co(II) and Mn(II)) complexes, namely Co(1)2·2C2H5OH and Mn(2)2·2C2H5OH, with unusual seven-membered metallo-ring units were synthesized successfully. In the solid state, complexes 5 and 6 adopt a novel hydrogen-bonded one-dimensional chain motif.
