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Barbara Zajc - One of the best experts on this subject based on the ideXlab platform.
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Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia–Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...
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regiospecifically fluorinated polycyclic aromatic hydrocarbons via julia kocienski olefination and oxidative photocyclization effect of fluorine atom substitution on molecular shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...
Shaibal Banerjee - One of the best experts on this subject based on the ideXlab platform.
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Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia–Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...
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regiospecifically fluorinated polycyclic aromatic hydrocarbons via julia kocienski olefination and oxidative photocyclization effect of fluorine atom substitution on molecular shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...
Kazutaka Itoh - One of the best experts on this subject based on the ideXlab platform.
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Determination of Chrysene degradation under saline conditions by Fusarium sp. F092, a fungus screened from nature.
Fungal biology, 2012Co-Authors: Asep Hidayat, Sanro Tachibana, Kazutaka ItohAbstract:Abstract Sixty-two rotted wood and soil samples were used to screen for Chrysene-degrading fungi. A strain of Fusarium , named F092, was identified as most capable of degrading Chrysene. F092 was active under saline and nonsaline conditions, breaking down 48 % of the Chrysene in 30 d. The percentage of Chrysene degraded did not change at 35 ‰ salinity with pH 8.2 in solid and liquid cultures. The degradation under saline conditions increased about 0.6- and 2.1-fold in cultures with polypeptone and Tween80, and 0.03-fold in agitated cultures. F092 secreted nonligninolytic enzymes named 1,2-dioxygenase and 2,3-dioxygenase. The level of 1,2-dioxygenase activity reached 203.5 U L −1 at 30 d and that of 2,3-dioxygenase activity, 29.7 U L −1 at 40 d. The degradation pathway was clarified from the intermediates produced; Chrysene 1,2-oxide, Chrysene trans -1,2-dihydrodiol, 1-hydroxy 2-naphtoic acid, and catechol. F092 is a potential degrader of Chrysene for bioremediation.
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biodegradation of Chrysene an aromatic hydrocarbon by polyporus sp s133 in liquid medium
Journal of Hazardous Materials, 2009Co-Authors: Tony Hadibarata, Sanro Tachibana, Kazutaka ItohAbstract:Abstract Polyporus sp. S133, a fungus collected from contaminated-soil was used to degrade Chrysene, a polycyclic aromatic hydrocarbon (PAH) in a mineral salt broth (MSB) liquid culture. Maximal degradation rate of Chrysene (65%) was obtained when Polyporus sp. S133 was incubated in the cultures supplemented with polypeptone (10%) for 30 days under agitation of 120 rpm, as compared to just 24% degradation rate in non-agitated culture. Furthermore, the degradation of Chrysene was affected by the addition of carbon and nitrogen sources as well as kind of surfactants. The degradation rate was increased with increase in added amount of carbon and nitrogen sources, respectively. The degradation rate in agitated cultures was enhanced about 2 times higher than that in non-agitated cultures. The degradation mechanism of Chrysene by Polyporus sp. S133 was determined through identification of several metabolites; Chrysenequinone, 1-hydroxy-2-naphthoic acid, phthalic acid, salicylic acid, protocatechuic acid, gentisic acid, and catechol. Several enzymes (manganese peroxidase, lignin peroxidase, laccase, 1,2-dioxygenase and 2,3-dioxygenase) produced by Polyporus sp. S133 were detected during the incubation. The highest enzyme activity was shown by 1,2-dioxygenase (237.5 U l−1) after 20 days of incubation.
Jong-wook Park - One of the best experts on this subject based on the ideXlab platform.
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New ultra deep blue emitters based on Chrysene chromophores
Organic Light Emitting Materials and Devices XX, 2016Co-Authors: Hwangyu Shin, Hyocheol Jung, Beomjin Kim, Jaehyun Lee, Seokwoo Kang, Hayoon Lee, Jong-wook ParkAbstract:Chrysene, which has a wide band gap, was selected as an emission core to develop and study new materials that emit ultra-deep-blue light with high efficiency. Six compounds introducing various side groups were designed and synthesized: 6, 12-bis(30,50-diphenylphenyl)Chrysene (TP-C-TP), 6-(30,50-diphenylphenyl)-12-(3,5-diphenylbiphenyl-400-yl)Chrysene (TP-C-TPB) and 6,12-bis(300,500-diphenylbiphenyl-40-yl)Chrysene (TPB-C-TPB), which contained bulky aromatic si de groups; and N,N,N0 ,N0-tetraphenyl-Chrysene-6,12-diamine (DPA-C-DPA), [12-(4-diphenylamino-phenyl)-Chrysene-6-yl]-diphenylamine(DPA-C-TPA) and 6,12-bis[4-(diphenylamino)phenyl]Chrysene (TPA-C-TPA), which contained aromatic amine groups, were designed to afford improved hole injection properties. The synthesized materials showed maxi mum absorption wavelengths at 342–402 nm in the film state and exhibited deep-blue photoluminescence (PL) emission s at 417–464 nm. The use of TP-C-TPB in a non-doped organic light emitting diode (OLED) device resulted in ultra-deep-blue emission with an external quantum efficiency (EQE) of 4.02% and Commission Internationale de L’Eclairage coo rdinates (CIE x, y) of (0.154, 0.042) through effective control of the internal conjugation length and suppression of the p –p* stacking. The use of TPA-C-TPA, which includes an aromatic amine side group, afforded an excellent EQE of 4.83 % and excellent color coordinates CIE x, y of (0.147, 0.077).
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Highly efficient emitters of ultra-deep-blue light made from Chrysene chromophores
Journal of Materials Chemistry C, 2016Co-Authors: Hwangyu Shin, Hyocheol Jung, Beomjin Kim, Jaehyun Lee, Jiwon Moon, Joonghan Kim, Jong-wook ParkAbstract:Chrysene, which has a wide band gap, was selected as an emission core to develop and study new materials that emit ultra-deep-blue light with high efficiency. Six compounds introducing various side groups were designed and synthesized: 6,12-bis(3′,5′-diphenylphenyl)Chrysene (TP-C-TP), 6-(3′,5′-diphenylphenyl)-12-(3\,5\-diphenylbiphenyl-4′′-yl)Chrysene (TP-C-TPB) and 6,12-bis(3′′,5′′-diphenylbiphenyl-4′-yl)Chrysene (TPB-C-TPB), which contained bulky aromatic side groups; and N,N,N′,N′-tetraphenyl-Chrysene-6,12-diamine (DPA-C-DPA), [12-(4-diphenylamino-phenyl)-chrysen-6-yl]-diphenylamine (DPA-C-TPA) and 6,12-bis[4-(diphenylamino)phenyl]Chrysene (TPA-C-TPA), which contained aromatic amine groups, were designed to afford improved hole injection properties. The synthesized materials showed maximum absorption wavelengths at 342–402 nm in the film state and exhibited deep-blue photoluminescence (PL) emissions at 417–464 nm. The use of TP-C-TPB in a non-doped organic light-emitting diode (OLED) device resulted in ultra-deep-blue emission with an external quantum efficiency (EQE) of 4.02% and Commission Internationale de L'Eclairage coordinates (CIE x, y) of (0.154, 0.042) through effective control of the internal conjugation length and suppression of the π–π* stacking. The use of TPA-C-TPA, which includes an aromatic amine side group, afforded an excellent EQE of 4.83% and excellent color coordinates CIE x, y of (0.147, 0.077).
Saikat Sinha - One of the best experts on this subject based on the ideXlab platform.
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Regiospecifically Fluorinated Polycyclic Aromatic Hydrocarbons via Julia–Kocienski Olefination and Oxidative Photocyclization. Effect of Fluorine Atom Substitution on Molecular Shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...
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regiospecifically fluorinated polycyclic aromatic hydrocarbons via julia kocienski olefination and oxidative photocyclization effect of fluorine atom substitution on molecular shape
Journal of Organic Chemistry, 2016Co-Authors: Shaibal Banerjee, Saikat Sinha, Alessio Caruso, Daniel Liebowitz, Miriam Rossi, Damon A Parrish, Padmanava Pradhan, Barbara ZajcAbstract:A modular synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons (PAHs) is described. 1,2-Diarylfluoroalkenes, synthesized via Julia–Kocienski olefination (70–99% yields), were converted to isomeric 5- and 6-fluorobenzo[c]phenanthrene, 5-and 6-fluoroChrysene, and 9- and 10-benzo[g]Chrysene (66–83% yields) by oxidative photocyclization. Photocyclization to 6-fluoroChrysene proceeded more slowly than conversion of 1-styrylnaphthalene to Chrysene. Higher fluoroalkene dilution led to a more rapid cyclization. Therefore, photocyclizations were performed at higher dilutions. To evaluate the effect of fluorine atom on molecular shapes, X-ray data for 5- and 6-fluorobenzo[c]phenanthrene, 6-fluoroChrysene, 9- and 10-fluorobenzo[g]Chrysene, and unfluorinated Chrysene as well as benzo[g]Chrysene were obtained and compared. The fluorine atom caused a small deviation from planarity in the Chrysene series and decreased nonplanarity in the benzo[c]phenanthrene derivatives, but its influence was most...