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Polyenes and Polyvinylenes

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Acetylene and Its Polymers

Part of the book series: SpringerBriefs in Molecular Science ((BRIESFHISTCHEM))

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Abstract

Although not produced via the direct polymerization of acetylene, the following chapter will introduce the history of two earlier materials structurally related to the later formal polyacetylene . These two classes of materials were known as polyenes and polyvinylenes, two terms that at times have been used synonymously with polyacetylene.

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Notes

  1. 1.

    It was renamed the Max Plank Institut in 1950.

  2. 2.

    Some sources state that his doctoral research was under Hans Brockmann (1903–1988), Director of the Institute for Organic Chemistry at Göttingen. However, Bohlmann’s thesis topic is very much in line with the research focus of Dimroth and the work appears to have been under his direction.

  3. 3.

    This is now known as the Wittig reaction or Wittig olefination, for which Wittig was awarded the Nobel Prize in Chemistry in 1979.

  4. 4.

    See Chap. 5.

References

  1. Rasmussen SC (2014) The path to conducting polyacetylene. Bull Hist Chem 39:64–72

    CAS  Google Scholar 

  2. Rasmussen SC (2017) Cuprene: a historical curiosity along the path to polyacetylene. Bull Hist Chem 42:63–78

    CAS  Google Scholar 

  3. Shirakawa H (2001) The discovery of polyacetylene film: the dawning of an era of conducting polymers. In: Frängsmyr T (ed) Les Prix Nobel. The Nobel Prizes 2000, Nobel Foundation, Stockholm, pp 217–226

    Google Scholar 

  4. Shirakawa H (2001) The discovery of polyacetylene film: the dawning of an era of conducting polymers (Nobel lecture). Angew Chem Int Ed 40:2574–2580

    Article  Google Scholar 

  5. Shirakawa H (2001) Nobel lecture: the discovery of polyacetylene film—the dawning of an era of conducting polymers. Rev Mod Phys 73:713–718

    Article  CAS  Google Scholar 

  6. Shirakawa H (2002) The discovery of polyacetylene film. The dawning of an era of conducting polymers. Synth Met 125:3–10

    Article  CAS  Google Scholar 

  7. Kuhn R, Winterstein A (1928) Über konjugierte Doppelbindungen I. Synthese von Diphenyl-poly-enen. Helv Chim Acta 11:87–116

    Article  CAS  Google Scholar 

  8. Kuhn R, Winterstein A (1928) Über konjugierte Doppelbindungen II. Synthese von Biphenylen-poly-enen. Helv Chim Acta 11:116–122

    Article  CAS  Google Scholar 

  9. Kuhn R, Winterstein A (1928) Über konjugierte Doppelbindungen III. Wasserstoff- und Brom-anlagerung an Poly-ene. Helv Chim Acta 11:123–144

    Article  CAS  Google Scholar 

  10. Kuhn R, Winterstein A (1928) Über konjugierte Doppelbindungen IV. Molekelverblndungen und Farbreaktionen der Poly-ene. Helv Chim Acta 11:144–151

    Article  CAS  Google Scholar 

  11. Baer HH (1969) Richard Kuhn 1900–1967. Adv Carbohydr Chem 24:1–11

    CAS  Google Scholar 

  12. Baer HH (1993) Richard Kuhn (1900–1967): Werk und Persönlichkeit. Liebigs Ann Chem 1993(11):I–XXX1

    Google Scholar 

  13. Kuhn R (1937) Über die Synthese höherer Polyene. Angew Chem 50:703–708

    Article  CAS  Google Scholar 

  14. Hengstenberg J, Kuhn R (1930) Die Kristallstruktur der Diphenylpolyene. Z Kristallogr Kristallgeom Kristallphys Kristallchem 75:301–310

    CAS  Google Scholar 

  15. Hausser KW, Kuhn R, Smakula A (1935) Lichtabsorption und Doppelbindung. IV. Diphenylpolyene. Z Phys Chem Abt B 29:384–389

    Google Scholar 

  16. Hausser KW, Kuhn R, Seitz G (1935) Lichtabsorption und Doppelbindung. V. Über die Absorption von Verbindungen mit konjugierten Kohlenstoffdoppelbindungen bei tiefer Temperatur. Z Phys Chem Abt B 29:391–416

    Google Scholar 

  17. Hausser KW, Kuhn R, Kuhn E (1935) Lichtabsorption und Doppelbindung. VI. Über die Fluorescenz der Diphenylpolyene. Z Phys Chem Abt B 29:417–454

    Google Scholar 

  18. Kuhn R, Grundmann C (1938) Uber die Synthese von 1.6-Dimethyl-hexatrien, 1.8-Dimethyl-octatetraen und 1.12-Dimethyl-dodecahexaen. Ber Dtsch Chem Ges 71B:442–447

    Article  CAS  Google Scholar 

  19. Blout ER, Fields M (1948) Absorption spectra. V. The ultraviolet and visible spectra of certain polyene aldehydes and polyene azines. J Am Chem Soc 70:189–193

    Article  CAS  Google Scholar 

  20. Blout ER, Fields M, Karplus R (1948) Absorption spectra. VI. The infrared spectra of certain compounds containing conjugated double bonds. J Am Chem Soc 70:194–198

    Article  CAS  Google Scholar 

  21. Blout ER (2002) Oral History Interview conducted by Bohning JJ, Thackray A (Transcript #0263) at Harvard Medical School, Harvard School of Public Health, and Cambridge, Massachusetts. Chemical Heritage Foundation, Philadelphia, 30 May 1991, 13 September and 22 November 2002

    Google Scholar 

  22. Pearce J (2007) Elkan R. Blout, Scientist at Harvard, Dies at 86. The New York Times, January 9

    Google Scholar 

  23. Bohlmann F (1952) Reaktionen mit Lithiumaluminiunhydrid: Reduktion von Polyen-1.2-diketonen, zugleich eine Methode zur Darstellung von Polyenen. Chem Ber 85:386–389

    Article  CAS  Google Scholar 

  24. Winterfeldt E (1994) Ferdinand Bohlmann (1921–1991) und sein wissenschaftliches Werk. Liebigs Ann Chem 1994(5):I–XXXIV

    Article  Google Scholar 

  25. Bohlmann F (1946) Solvatochromie in der Pyridinreihe. Ph.D. Dissertation, University of Göttingen

    Google Scholar 

  26. Karrer P, Coehand C (1945) Di-[ω-phenyl-polyen]-diketone. Helv Chim Acta 28:1181–1184

    Article  CAS  Google Scholar 

  27. Bohlmann F, Mannhardt HJ (1956) Konstitution und Lichtabsorption, VIII. Mitteil. 1): Darstellung und Lichtabsorption von Dimethyl-polyenen. Chem Ber 89:1307–1315

    Article  CAS  Google Scholar 

  28. Wittig G, Schöllkopf U (1954) Über Triphenyl-phosphin-methylene als olefinbildende Reagenzien (I. Mitteil.). Chem Ber 87:1318–1330

    Article  Google Scholar 

  29. Woods GF, Schwartzman LH (1948) 1,3,5-Hexatriene. J Am Chem Soc 70:3394–3396

    Article  CAS  PubMed  Google Scholar 

  30. Woods GF, Schwartzman LH (1949) 1,3,5,7-Octatetraene. J Am Chem Soc 71:1396–1399

    Article  CAS  Google Scholar 

  31. Mebane AD (1952) 1,3,5,7,9-Decapentaene and 1,3,5,7,9,11,13-tetradecaheptaene. J Am Chem Soc 74:5527–5529

    Article  Google Scholar 

  32. Sondheimer F, Ben-Efraim DA, Wolovsky R (1961) Unsaturated macrocyclic compounds. XVII. The prototropic rearrangement of linear 1,5-enynes to conjugated polyenes. The synthesis of a series of vinylogs of butadiene. J Am Chem Soc 83:1675–1681

    Article  CAS  Google Scholar 

  33. Boyer RF (1947) A statistical theory of discoloration for halogen-containing polymers and copolymers. J Phys Colloid Chem 51:80–160

    Article  CAS  PubMed  Google Scholar 

  34. Fuoss RM (1938) Preparation of polyvinyl chloride plastics for electrical measurements. Trans Electrochem Soc 74:91–112

    Article  Google Scholar 

  35. Marvel CS, Sample JH, Roy MF (1939) The structure of vinyl polymers. VI. Polyvinyl halides. J Am Chem Soc 61:3241–3244

    Article  CAS  Google Scholar 

  36. Winkler DE (1959) Mechanism of poly(vinyl chloride) degradation and stabilization. J Polym Sci 35:3–16

    Article  CAS  Google Scholar 

  37. Sadron C, Parrod J, Roth JP (1960) On the dehydrochlorination of polyvinyl chloride. Compt Rend 250:2206–2208

    CAS  Google Scholar 

  38. Bengough WI, Sharpe HM (1963) The thermal degradation of polyvinylchoride in solution. I. The kinetics of the dehydrochlorination reactin. Makromol Chem 66:31–44

    Article  CAS  Google Scholar 

  39. Tsuchida E, Shih CN, Shinohara I, Kambara S (1964) Synthesis of a polymer chain having conjugated unsaturated bonds by dehydrohalogenation of polyhalogen-containing polymers. J Polym Sci A 2:3347–3354

    CAS  Google Scholar 

  40. Kaesche-Krischer B, Heinrich HJ (1960) Pyrolyse und Entzündung von Polyvinylalkohol (PVA). Z Phys Chem 23:292–296

    Article  CAS  Google Scholar 

  41. Mainthia SB, Kronick PL, Labes MM (1962) Electrical measurements on polyvinylene and polyphenylene. J Chem Phys 37:2509–2510

    Article  CAS  Google Scholar 

  42. Tsuchiya Y, Sumi K (1969) Thermal decomposition products of poly(vinyl alcohol). J Polym Sci A: Polym Chem 7:3151–3158

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, North Dakota State University, Fargo, ND, USA

    Seth C. Rasmussen

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Correspondence to Seth C. Rasmussen .

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Rasmussen, S.C. (2018). Polyenes and Polyvinylenes. In: Acetylene and Its Polymers. SpringerBriefs in Molecular Science(). Springer, Cham. https://doi.org/10.1007/978-3-319-95489-9_4

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