Abstract
The cocrystallization and copolymerization of two pairs of diacetylenes R–C≡C–C≡C–R, (1) 1 BU [R=–CH2OCONHC4H9] and 1 EU [R=–CH2OCONHC2H5], and (2) 2A [R=–(CH2)2OH] and 3A [R=(CH2)3OH] was studied by differential scanning calorimetry and reflectance spectroscopy. Several novel features were observed. 1 BU always crystallizes into a mixture of two phases, blue (λmax=585 nm) and red (λmax=515 nm). 1 EU and 1 BU cocrystallize to form solid solutions as evidenced by singlet endotherms or by different reflectance spectra. λmax, the lowest energy optical transitions of partially polymerized cocrystallized mixtures, increases as the concentration of 1 EU increases to about 90%. Mixtures of 2A and 3A form amorphous solid solutions. The amorphous solid solutions crystallize in the solid state before melting. DSC shows an exotherm followed by an endotherm during heating. Partially polymerized 3A changes from blue→red when touched by human hands. The color change is due to melting of unreacted monomer.
Similar content being viewed by others
Log in or create a free account to read this content
Gain free access to this article, as well as selected content from this journal and more on nature.com
or
References
J. E. Herz and V. Stannett, J. Polym. Sci., Polym. Phys. Ed., 3, 1 (1969).
Y. Tabata, “Advances in Macromolecular Chemistry,” Vol. 1, W. M. Pasika, Ed., Academic Press, New York, 1968.
G. G. Miller and G. N. Patel, J. Appl. Polym. Sci., 24, 883 (1979).
V. Enkelmann, Makromol. Chem., 179, 2811 (1978).
V. Enkelmann, J. Mater. Sci., 15, 651 (1980).
G. Wegner, Z. Naturforsch, B24, 824 (1969).
G. Wegner, Makromol. Chem., 134, 219 (1970).
G. Wegner, Makromol. Chem., 145, 85 (1971).
G. Wegner, Makromol. Chem., 154, 35 (1979).
G. Wegner, “Molecular Metals,” W. E. Hatfield, Ed., Plenum Press, New York, 1979, pp 209—242.
G. N. Patel, R. R. Chance, E. A. Turi, and Y. P. Khanna, J. Am. Chem. Soc., 100, 6644 (1978).
Y. Hori and L. D. Kispert, J. Am. Chem. Soc., 101, 3173 (1979).
G. N. Patel, unpublished paper.
G. N. Patel, US Patent 4,164,458, assigned to Allied Chemical Corporation, U.S.A., February 1980.
G. N. Patel, Radiat. Phys. Chem., 14, 729 (1979).
A. S. Hay, J. Org. Chem., 27, 3320 (1962).
J. B. Armitage, C. L. Cook, N. Entwistle, E. R. H. Jones, and M. C. Whiting, J. Chem. Soc. (London), 1998 (1952).
G. N. Patel, E. N. Duesler, D. Y. Curtin, and I. C. Paul, J. Am. Chem. Soc., 102, 461 (1980).
G. N. Patel and G. G. Miller, J. Macromol. Sci., Phys., in press. The relationship between color and conformation of polydiacetylenes is explained in this reference.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Miller, G., Patel, G. Cocrystallization and Copolymerization of Diacetylenes: Some Novel Observations. Polym J 13, 1075–1083 (1981). https://doi.org/10.1295/polymj.13.1075
Issue date:
DOI: https://doi.org/10.1295/polymj.13.1075