Crossref journal-article
Wiley
Macromolecular Rapid Communications (311)
Abstract

AbstractIt is the general consensus that in Gilch polymerizations the 1,4‐bis(chloromethylene)benzene starting material first changes into p‐quinodimethane intermediates which then act as the real monomers. However, direct observation of these intermediates has not been possible so far. This is because usually the p‐quinodimethane auto‐initiates its rapid radical polymerization instantaneously, keeping its concentration extremely low throughout the whole process. Here it is shown that, when the reaction is carried out at very low temperatures, the formation of p‐quinodimethane still proceeds but chain growth is suppressed. Hence, the concentration of the active monomer reaches a level sufficient for NMR analysis.magnified image

Bibliography

Wiesecke, J., & Rehahn, M. (2007). Direct Observation of α‐Chloro‐p‐quinodimethane as the Real Monomer in the Gilch Polymerization Leading to Poly(p‐phenylene vinylene)s. Macromolecular Rapid Communications, 28(2), 188–193. Portico.

Authors 2
  1. Jens Wiesecke (first)
  2. Matthias Rehahn (additional)
References 80 Referenced 22
  1. 10.1038/347539a0
  2. 10.1002/(SICI)1521-3757(19980216)110:4<416::AID-ANGE416>3.0.CO;2-N
  3. 10.1002/polc.5070720109
  4. 10.1016/j.polymer.2005.05.001
  5. 10.1016/j.polymer.2004.12.029
  6. 10.1021/ma049545u
  7. 10.1021/ma030025t
  8. 10.1016/0379-6779(94)02548-D
  9. 10.1021/ma00108a079
  10. 10.1016/0379-6779(92)90025-E
  11. 10.1021/ja021295e
  12. 10.1016/S0032-3861(02)00414-7
  13. 10.1021/ma020694r
  14. 10.1039/b106115c
  15. 10.1126/science.269.5222.376
  16. 10.1016/j.polymer.2005.11.007
  17. 10.1021/ma021221n
  18. 10.1002/adma.19950070105
  19. {'key': 'e_1_2_7_23_2', 'first-page': '505', 'volume': '31', 'author': 'Swatos W. J.', 'year': '1990', 'journal-title': 'Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.)'} / Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) by Swatos W. J. (1990)
  20. 10.1002/pol.1966.150040602
  21. 10.1002/pol.1966.150040602
  22. 10.1002/macp.1997.021980516
  23. 10.1021/ma00072a002
  24. 10.1002/macp.1991.021920419
  25. 10.1002/macp.1990.021910511
  26. 10.1002/macp.1988.021890112
  27. 10.1002/macp.1997.021980517
  28. 10.1002/marc.1990.030110806
  29. 10.1021/ja00099a085
  30. 10.1021/ja00050a088
  31. 10.1002/(SICI)1521-3927(19980401)19:4<223::AID-MARC223>3.0.CO;2-7
  32. 10.1002/marc.1995.030160209
  33. 10.1002/(SICI)1521-3935(19990801)200:8<1870::AID-MACP1870>3.0.CO;2-T
  34. 10.1021/ma00122a023
  35. 10.1021/ja01502a054
  36. 10.1038/365628a0
  37. 10.1021/ma0004108
  38. 10.1002/(SICI)1521-4095(199907)11:10<814::AID-ADMA814>3.0.CO;2-Z
  39. 10.1002/adma.19970090608
  40. 10.1016/0379-6779(94)90013-2
  41. 10.1246/cl.1991.1071
  42. 10.1002/pol.1966.150041209
  43. 10.1021/ma0118116
  44. 10.1039/b314418f
  45. 10.1021/cm0209113
  46. 10.1021/ma025505j
  47. 10.1021/ja003135d
  48. 10.1021/jp993190c
  49. 10.1021/ma990217h
  50. 10.1016/0009-2614(93)E1421-C
  51. 10.1016/0379-6779(94)90004-3
  52. 10.1016/0032-3861(89)90077-3
  53. 10.1002/(SICI)1521-4095(200001)12:1<42::AID-ADMA42>3.0.CO;2-F
  54. 10.1021/ma030025t
  55. 10.1021/ma990347q
  56. 10.1002/ange.200390131
  57. 10.1021/ma020992o
  58. 10.1002/app.1847
  59. 10.1016/S0032-3861(01)00076-3
  60. 10.1021/ma991521d
  61. 10.1016/S0040-6090(99)01026-3
  62. {'key': 'e_1_2_7_74_2', 'first-page': '541', 'volume': '18', 'author': 'Pan J.‐Q.', 'year': '2000', 'journal-title': 'Chin. J. Polym. Sci.'} / Chin. J. Polym. Sci. by Pan J.‐Q. (2000)
  63. 10.1016/S0032-3861(99)00486-3
  64. 10.1016/S0032-3861(99)00242-6
  65. 10.1021/ma9713771
  66. 10.1016/S0032-3861(96)00468-5
  67. B. R.Hsieh U. S. Patent 5 817 430.
  68. 10.1021/ja00708a073
Dates
Type When
Created 18 years, 7 months ago (Jan. 22, 2007, 5:17 a.m.)
Deposited 1 year, 10 months ago (Oct. 10, 2023, 7:47 a.m.)
Indexed 1 year, 10 months ago (Oct. 18, 2023, 2:50 a.m.)
Issued 18 years, 7 months ago (Jan. 22, 2007)
Published 18 years, 7 months ago (Jan. 22, 2007)
Published Online 18 years, 7 months ago (Jan. 22, 2007)
Published Print 18 years, 7 months ago (Jan. 23, 2007)
Funders 0

None

@article{Wiesecke_2007, title={Direct Observation of α‐Chloro‐p‐quinodimethane as the Real Monomer in the Gilch Polymerization Leading to Poly(p‐phenylene vinylene)s}, volume={28}, ISSN={1521-3927}, url={http://dx.doi.org/10.1002/marc.200600649}, DOI={10.1002/marc.200600649}, number={2}, journal={Macromolecular Rapid Communications}, publisher={Wiley}, author={Wiesecke, Jens and Rehahn, Matthias}, year={2007}, month=jan, pages={188–193} }