Abstract
The photo-initiated solid-state topochemical polymerization of 1,1,4,4-bis(pentamethylene)-1,2,3-butatriene (1) was attempted unsuccessfully. Since 1 readily polymerizes in the liquid state, a structural study was undertaken to better understand its inertness in the solid-state. 1 crystallizes in the monoclinic space group P21/n with a = 6.4597(6), b = 10.8914 (10), c = 8.4396(8) Å, β = 100.168(2)°, V = 584.44(9) Å3, and Z = 2. The crystal structure reveals that while the alignment of the π-systems in the solid-state is acceptable for supporting the targeted polymerization reaction, the reaction centers are located too far apart to allow the reaction to take place. Additionally, comparison of the molecular structure of 1 with the limited number of other structurally characterized butatrienes has provided insight into the steric and electronic influences played by the substituents attached to the cumulene moiety.
Similar content being viewed by others
References
Current address: Department of Chemistry, University of Florida, Gainseville, FL 32611.
Pollack, S.K.; Fiseha, A. Macromol. 1997, 30, 5265.
Pollack, S.K.; Fiseha, A. Macromol. 1998, 31, 2002
Polydiacetyelenes, Cantow, H.-J. Ed., Advances in Polymer Sciences 63, Springer-Verlag: Berlin, 1984.
Bachman, R.E.; Andretta, D.F Inorg. Chem. 1998, 37, 5657.
SHELXTL-PC (Version 5.03) Siemens Analytical X-ray Instruments: Madison, WI.
Schmidt, G.M.J. Pure. Appl. Chem. 1971, 27, 647, and references therein. (b) Frank, J.K.; Paul, I.C. J. Am. Chem. Soc. 1973, 95, 2324.
Berkovitch-Yellin, Z.; Leiserowitz, L. Acta Crystalogr. 1977, B33, 3657.
Irngartinger, H.; Jäger, H.-U. Angew. Chem. Int. Ed. Engl. 1976, 15, 562.
Morimoto, Y.; Higuchi, Y.; Wakamatsu, K.; Oshima, K.; Utimoto, K.; Yasuoka, N. Bull. Chem. Soc. Jpn. 1989, 62, 639.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Bachman, R.E., Fiseha, A. & Pollack, S.K. The structure and attempted topochemical polymerization of single crystalline 1,1,4,4-bis(pentamethylene)-1,2,3-butatriene. Journal of Chemical Crystallography 29, 457–462 (1999). https://doi.org/10.1023/A:1009571228776
Issue Date:
DOI: https://doi.org/10.1023/A:1009571228776