Process for preparing pentacene derivatives

Details Process for preparing pentacene derivatives Process for preparing pentacene derivatives

2005-12-13

2005-12-13

Qazi, S. (Department: 1616)

Organic compounds -- part of the class 532-570 series

Organic compounds

Polycyclo ring system containing anthracene configured ring...

C540S145000, C568S633000, C568S300000, C568S068000, C570S183000, C257S040000

Reexamination Certificate

active

06974877

ABSTRACT:
A process for preparing substituted pentacene compounds comprises the step of cyclizing substituted bis(benzyl)phthalic acids using an acid composition comprising trifluoromethanesulfonic acid, the substituted bis(benzyl)phthalic acids being represented by the following general formulas:wherein each R (that is, each of the groups R1through R8) is independently an electron-donating group, a halogen atom, a hydrogen atom, or a combination thereof.

REFERENCES:
patent: 3627655 (1971-12-01), Perez-Albuerne
patent: 5707779 (1998-01-01), Naito
patent: 6165383 (2000-12-01), Chou
patent: 6465116 (2002-10-01), Ishikawa et al.
patent: 6489046 (2002-12-01), Ikeda et al.
patent: 0 726 304 (1996-08-01), None
patent: 0 786 820 (1997-07-01), None
patent: 63-199759 (1988-08-01), None
patent: 11-354277 (1999-12-01), None
patent: WO 00/03565 (2000-01-01), None
patent: WO 00/56933 (2000-09-01), None
patent: 01/45469 (2001-06-01), None
patent: WO 01/45469 (2001-06-01), None
patent: WO 03/016599 (2003-02-01), None
Machek, Guido, AN 24:46489, CA, Monatsh. (1930), 56, 116-34 (Full reference is also enclosed along with English abstract.
Philippi, Ernst et al, AN 17:11407 CA, Monatsh. (1923), 43, 615-9, 621-31. (Full reference is also enclosed along with English abstract).
B. Hulin et al.,“A Convenient, Mild Method for the Cyclization of 3- and 4-Arylalkanoic Acids via Their Trifluoromethanesulfonic Anhydride Derivatives”,J. Org. Chem., vol. 49, (1984), pp. 207-209.
T. Yamato et al.,“Organic Reactions Catalyzed by Solid Superacids. 5.1Perfluorinated Sulfonic Acid Resin(Nafion-H)Catalyzed Intramolecular Friedel-Crafts Acylation”,J. Org. Chem., vol. 56, No. 12, (1991), pp. 3955-3957.
V. Premasagar et al.,“Methanesulfonic Acid Catalyzed Cyclization of 3-Arylpropanoic and 4-Arylbutanoic Acids to 1-Indanones and 1-Tetralones”,J. Org. Chem., vol. 46, No. 14, (1981), pp. 2974-2976.
Mills and Mills: The Synthetical Production of Derivatives of Dinaphthanthracene“CCXXX.—The Synthetical Production of Derivatives of Dinaphthanthracene”,J. Chem. Soc., vol. 101, (1912), pp. 2194-2208.
J. M. Shaw et al.,“Organic Electronics: Introduction”,IBM J. Res. & Dev., vol. 45, No. 1, (Jan. 2001), pp. 3-9.
C. D. Dimitrakopoulos et al.,“Organic Thin-Film Transistors: A Review of Recent Advances”,IBM J. Res. & Dev., vol. 45, No. 1, (Jan. 2001), pp. 11-27.
C. D. Dimitrakopoulos et al.,“Molecular Beam Deposited Thin Films of Pentacene for Organic Field Effect Transistor Applications”,J. Appl. Phys., vol. 80, No. 4, (Aug. 15, 1996), pp. 2501-2508.
D. J. Gundlach et al.,“Solvent-Induced Phase Transition in Thermally Evaporated Pentacene Films”,Appl. Phys. Lett., vol. 74, No. 22, (May 31, 1999), pp. 3302-3304.
Y.-Y. Lin et al.,“Stacked Pentacene Layer Organic Thin-Film Transistors with Improved Characteristics”IEEE Electron Device Letters, vol. 18, No. 12, (Dec. 1997), pp. 606-608.
A. Orita et al.,“Integrated Chemical Process: One-Pot Aromatization of Cyclic Enones by the Double Elimination Methodology”Angew. Chem. Int. Ed., vol. 38, No. 15, (1999) pp. 2267-2270.
A. R. Wartini et al.,“Intramolecular Electron Transfer Between Terminal 1,4-Dimethoxybenzene Units in Radical Cations with a [2.2](1,4)Naphthalenophane, [2.2](1,4)Anthracenophane, and Pentacene Skeleton”,Eur. J. Org. Chem., (1998), pp. 1161-1170.
Kirk-Othmer Enc. Of Chemical Technology,“Friedel-Crafts Reactions”, vol. 11, 4thed.,John Wiley & Sons, Inc., NY, (1994), pp. 1043-1075.
E. Philippi et al.,“Dinaphthanthracene Series V, VI”,Monatshefte Fur Chemie, vol. 43, (1923), pp. 615-619.
E. Philippi,“Synthesis of Linear Diphthaloyl Benzene”,Monatshefte Fur Chemie, vol. 32, (1911), pp. 631-635.
E. Philippi,“Condensation of Pyromellitic Anhydride with Benzene and Toluene”,Monatshefte Fur Chemie, vol. 34, (1913), pp. 705-715.
E. Philippi et al.,“Dinaphthanthracene Series IV Bromo Derivatives”,Monatshefte Fur Chemie, vol. 42, (1921), pp. 1-4.
G. Machek,“Linear Pentacene Serie XIX Constitution of the Bi-derivatives of 5,7,12,14-Pentacenediquinone”,Monatshefte Fur Chemie, vol. 56, (1930), pp. 116-134.
H. E. Katz et al.,“Synthetic Chemistry for Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors”,American Chemical Society, Accounts of Chemical Research, vol. 34, No. 5, (2001), pp. 359-369.
S. M. Sze,Physics of Semiconductor Devices,MOSFET Structures, 8.5.6 Thin-Film Transistor, 2nded., John Wiley & Sons, (1981), pp. 492-493.
S. M. Sze,Physics of Semiconductor Devices,MOSFET Basic Device Characteristics, 8.2.2 Linear and Saturation Regions, 2nded., John Wiley & Sons, (1981), pp. 438-442.
J. M. Allen et al.,“Friedel-Crafts Cyclisation-VI1Polyphosphoric Acid-Catalysed Reactions of Crotonophenones and Chalcones”,Tetrahedon, vol. 33, (1977), pp. 2083-2087.
H. de Diesbach et al.“Derivatives of Dinaphthanthracene Diquinone and the Synthesis of Dinaphthaleneanthracene Diquinone”,Helvetica Chim. Acta, vol. 7, (1924), pp. 644-653.
E. Clar et al.,“Information on Polycyclic Aromatic Hydrocarbons and Their Derivatives, V. Naphthoanthracene, Their Oxidation Products and a New Class of Deep-Colored Hydrocarbons”,Chem Berichte, (1929), 3027-3032.
E. Clar et al.,“Information on Polycyclic Aromatic Hydrocarbons and Their Derivatives, II. [Naphtho-2′,3′:1,2-anthracene]1).Its Homologues and its Oxidation Products”,Chem Berichte, (1929). p. 940-947.
E. Clar et al.,“Information on Polycyclic Aromatic Hydrocarbons and Their Derivatives, VIII. [Naphtho-2′,3′:1,2-anthracene],[2,3:6,7-dibenzoanthracenes-9,10-diyls] and Their Oxidation Products”,Chem Berichte, (1929), p. 981-986.
F. Effenberger et al.,“Catalytic Friedel-Crafts Acylation of Aromatic Compounds”,Angew. Chem. Internat. Edit., vol. 11, No. 4 (1972), pp. 300-301.
G. A. Olah et al.,“Nafion-H Catalysed Intramolecular Friedel-Crafts Acylation : Formation of Cyclic Ketones and Related Heterocycles”,Synlett, No. 7, (1999), pp. 1067-1068.
S. Miki et al.,“Synthesis of 1,2,3,-Tri-t-butyl-6,13- and 8,9,10-Tri-t-butyl-5,14-pentacenequinones and Their Photochromic Behaviors: New Photochromic Molecules”,Tetrahedron, vol. 52, No. 12, (1996), pp. 4269-4276.
T. Takahashi, et al.,“Straightforward Method for Synthesis of Highly Alkyl-Substituted Naphthacene and Pentacene Derivatives by Homologation”,J. Am. Chem. Soc., (2000), pp. 12876-12877, vol. 122.

Affiliated with

Also associated with

Rating

Process for preparing pentacene derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for preparing pentacene derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for preparing pentacene derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3482006