Mixed halogen polymerization

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C528S377000

Reexamination Certificate

active

07838624

ABSTRACT:
Synthesis of regioregular thiophene-based polymers (PTs) and their functionalized counterparts via metal assisted cross-coupling polymerizations utilizing mixed halogen substituted aryl halide monomer precursors. The described method provides a means to control structural homogeneity and regioregularity and the electronic/spectroscopic properties of functionalized PTs, and leads to improved performance of organic semiconductor devices such as OPVs and/or OFETs. Asymmetrical monomers can be used.

REFERENCES:
patent: 2005/0080219 (2005-04-01), Koller et al.
patent: 2006/0155105 (2006-07-01), Werner et al.
patent: 2007/0045614 (2007-03-01), Sugawara et al.
patent: 1 028 136 (2000-08-01), None
patent: 1582523 (2005-10-01), None
patent: WO2005/014691 (2005-02-01), None
patent: WO2006/084545 (2006-08-01), None
patent: WO2008/028166 (2008-03-01), None
U.S. Appl. No. 11/350,271, filed Feb. 9, 2006, Williams et al.
U.S. Appl. No. 11/376,550, filed Mar. 16, 2006, Williams et al.
U.S. Appl. No. 11/394,202, filed Mar. 31, 2006, McCullough et al.
U.S. Appl. No. 11/743,587, filed May 2, 2007, Laird et al.
U.S. Appl. No. 11/849,229, filed Aug. 31, 2007, McCullough et al.
U.S. Appl. No. 60/612,640, filed Sep. 24, 2004, Williams et al.
U.S. Appl. No. 60/612,641, filed Sep. 24, 2004, Williams et al.
U.S. Appl. No. 60/651,211, filed Feb. 10, 2005, Williams et al.
U.S. Appl. No. 60/661,934, filed Mar. 16, 2005, Williams et al.
U.S. Appl. No. 60/812,916, filed Jun. 13, 2006.
U.S. Appl. No. 60/841,548, filed Sep. 1, 2006, McCullough et al.
U.S. Appl. No. 60/915,632, filed May 2, 2007.
U.S. Appl. No. 60/938,166, filed May 15, 2007, Sheina et al.
Boymond et al., Angew. Chem. Int. Ed., vol. 37, No. 12, pp. 1701-1703 (1998).
Chen et al., “ ”, J. Am. Chem. Soc., vol. 117, pp. 233 (1995).
Greene and Greene, “Protective Groups in Organ Synthesis,” John Wiley & Sons, New York (1981).
Iovu et al., Macromolecules, vol. 38, pp. 8649 (2005).
Lowe et al., Adv. Mater., vol. 11, pp. 250 (1999).
March, Adv. Orgn. Chem., Reactions, Mechanisms, and Science, 6thEd., (2007).
McCullough et al., J. Org. Chem., vol. 58, pp. 904-912 (1993).
McCulough et al., Synth. Mt., vol. 67, pp. 279 (1995).
Sheina et al., Macromolecules, vol. 37, pp. 3526 (2004).
Weinshenker et al., J. Org. Chem., vol. 40, pp. 1966 (1975).
Anderson et al., “Regioselective Polymerization of 3-(4-Octylphenyl)thiophene with FeC13”, Macromolecules, vol. 27, No. 22, pp. 6503-6506 (1994).
Andersson et al., “Electroluminescence from substituted poly(thiophenes): from blue to near-infrared”, Macromolecules, vol. 28, pp. 7525-7529 (1995).
Andersson et al., “Synthesis of regioregular phenyl substituted polythiophenes with FeC13”, Synthetic Metals, vol. 101, pp. 11-12 (1999).
Corina et al., “Experimental Evidence for the Quasi-‘Living’ Nature of the Grignard Metathesis Method for the Synthesis of Regioregular Poly(3-alkylthiophenes)”, Macromolecules, vol. 38, pp. 8649-8656 (2005).
Goto et al., “Solvent-induced chiroptical changes in supramolecular assemblies of an optically active, regioregular polythiophene”, Macromolecules, vol. 35, pp. 4590-4601 (2002).
Jeffries-El et al., “Facile Synthesis of End-Functionalized Regioregular Poly(3-alkylthiophene)s via Modified Grignard Metathesis Reaction”, Macromolecules, vol. 38, pp. 10346-10352 (2005).
Johansson et al., “Light-emitting electrochemical cells from oligo(thylene oxide)-substituted polythiophenes: evidence for in situ doping”, Chem. Mater., vol. 11, pp. 3133-3139 (1999).
Loewe et al., “Regioregular, head-to-tail coupled poly(3-alkylthiphenes) made easily by the GRIM method: investigation of the reaction and the origin of the regioselectivity”, Macromolecules, vol. 34, pp. 4324-4333 (2001).
Mellah et al., “Electroreductive polymerization of 3-substituted 2,5-dihalothiophenes: direct electrosynthesis versus stepwise procedure involving thienylzinc intermediates”, New. J. Chem., vol. 26, pp. 207-212 (2002).
Tyo et al., “Synthesis of unsymmetrical 2, 3-diaryl-and 2,4-diarylthiophenes starting from 2,5-dichlorothiophene”, Bulletin of the Chem. Soc. of Japan, vol. 67, No. 8, pp. 2187-2194 (1994).
Yokoyama et al., “Chain-growth polymerization for poly(3-hexylthiophene) with a defined molecular weight and a low polydispersity”, Macromolecules, vol. 37, pp. 1169-1171 (2004).
Zhai et al., “A simple method to generate side-chain derivatives of regioregular polythiophene via the GRIM metathesis and post-polymerization functionalization”, Macromolecules, vol. 36, pp. 61-64 (2003).
PCT/US2008/006117 filed May 14, 2008, Intl. Search Report & Written Opinion mailed Jan. 13, 2009 (21 pages).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Mixed halogen polymerization does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Mixed halogen polymerization, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Mixed halogen polymerization will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-4195483

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.