Procedure for the Rapid Synthesis of the Monomer 1,4-Bis(chloromethyl)-2-(2-ethylhexyloxy)-5-methoxybenzene

REFERENCES

• Burroughes , J. H. ; Bradley , D. D. C. ; Brown , A. R. ; Marks , R. N. ; Mackay , K. ; Friend , R. H. ; Burns , P. L. ; Holmes , A. B. Light-emitting diodes based on conjugated polymers . Nature 1990 , 347 , 539 – 541 .
   Web of Science ®Google Scholar
• Braun , D. ; Heeger , A. J. Visible light emission from semiconducting polymer diodes . Appl. Phys. Lett. 1991 , 58 , 1982 – 1984 .
   Web of Science ®Google Scholar
• Halls , J. J. M. ; Walsh , C. A. ; Greenham , N. C. ; Marseglia , E. A. ; Friend , R. H. ; Moratti , S. C. ; Holmes , A. B. Efficient photodiodes from interpenetrating polymer networks . Nature 1995 , 376 , 498 – 501 .
   Web of Science ®Google Scholar
• Yu , G. ; Gao , J. ; Hummelen , J. C. ; Wudl , F. ; Heeger , A. J. Polymer photovoltaic cells: Enhanced efficiencies via a network of internal donor–acceptor heterojunctions . Science 1995 , 270 , 1789 – 1791 .
   Web of Science ®Google Scholar
• Wudl , F. ; Srdanov , G. Conducting polymer formed of poly[2-methoxy-5-(2-ethylhexyloxy)-p-phenylene vinylene . U.S. Patent 5,189,136, February 23, 1993 .
   Google Scholar
• Heeger , A. J. ; Braun , D. Visible-light-emitting diodes fabricated from soluble semiconducting polymers and their fabrication . U.S. Patent 5,408,109, April 18, 1995 .
   Google Scholar
• Lin , K.-F. ; Fan , Y.-L. ; Chow , H.-L. Origin of the methylene bonds in poly[2-methoxy-5-(2′-ethyl-hexyloxy)-1,4-phenylenevinylene] prepared according to Gilch's method: Novel applications . Polym. Int. 2006 , 55 , 938 – 944 .
   Web of Science ®Google Scholar
• Burn , P. L. ; Kraft , A. ; Baigent , D. R. ; Bradley , D. D. C. ; Brown , A. R. ; Friend , R. H. ; Gymer , R. W. ; Holmes , A. B. ; Jackson , R. W. Chemical tuning of the electronic properties of poly(p-phenylenevinylene)-based copolymers. J. Am. Chem. Soc. 1993, 115, 10117–10124.
   Web of Science ®Google Scholar
• Ahn , T. ; Jang , M. S. ; Shim , H.-K. ; Hwang , D.-H. ; Zyung , T. Blue electroluminescent polymers: Control of conjugation length by kink linkages and substituents in the poly(p-phenylenevinylene)-related copolymers . Macromolecules 1999 , 32 , 3279 – 3285 .
   Web of Science ®Google Scholar
• Amrutha , S. R. ; Jayakannan , M. Control of π-stacking for highly emissive poly(p-phenylenevinylene)s: Synthesis and photoluminescence of new tricyclodecane substituted bulky poly(p-phenylenevinylene)s and its copolymers . J. Phys. Chem. B 2006 , 110 , 4083 – 4091 .
   PubMed Web of Science ®Google Scholar
• Wood , J. H. ; Gibson , R. E. Di-(α- and β-substituted aminoethyl)-benzenes, I: 2,5-Bis-(2-aminoethyl)-hydroquinones . J. Am. Chem. Soc. 1949 , 71 , 393 – 395 .
   Web of Science ®Google Scholar
• Bis(chloromethyl) ether and technical-grade chloromethyl methyl ether CAS nos. 542-88-1 and 107-30-2 (substance 39) . In Report on Carcinogens , , 11th ed. ; U.S. Department of Health and Human Services, Public Health Service, National Toxicology Program, Washington, DC, 2005 .
   Google Scholar
• St. Clair , J. D. ; Valentine , J. R. Observation of bromomethyl ethers during the bromomethylation of aromatic compounds . Org. Proc. Res. Dev. 2005 , 9 , 1013 – 1014 .
   Web of Science ®Google Scholar
• Szmant , H. H. ; Dudek , J. Relative chloromethylation rates of some aromatic compounds . J. Am. Chem. Soc. 1949 , 71 , 3763 – 3765 .
   Web of Science ®Google Scholar