Abstract
Two series of monomers possessing two diphenylbutadiyne moieties connected by a methylene chain via amido groups, i.e., alkanedi{3-[4-(3-nitrophenyl)butadynyl]anilide} (N-n) and alkanedi{3-[4-(3-alkanoylaminophenyl)butadiynyl]anilide} (m A-n), were synthesized, and their solid-state polymerization behaviors and the polymer structures were investigated by various spectroscopic measurements and powder X-Ray diffractions. Although polymerization of N-n only proceeds in one of two diphenylbutadiyne moieties in a monomer to give single-chain polydiacetylenes, m A-n polymerized at both diphenylbutadiyne moieties to give double-chain polydiacetylenes. All the results suggest that two arrays of intermolecular hydrogen bonding formed between two diphenylbutadiyne moieties for N-n are not sufficient to fix the structure, and atomic movements during polymerization influence the polymerizable stack of the other remaining diphenylbutadiyne to disorder into non-polymerizable one. Meanwhile, m A-n can form four arrays of intermolecular hydrogen bonding on both sides of each diphenylbutadiyne moiety to fix it, and polydiactylene-based ladder polymers were successfully prepared from m A-n.
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Matsuo, H., Okada, S., Nakanishi, H. et al. Solid-State Polymerization of Monomers Possessing Two Diphenylbutadiyne Moieties with Amido Groups to Form Ladder Polymers. Polym J 34, 825–834 (2002). https://doi.org/10.1295/polymj.34.825
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DOI: https://doi.org/10.1295/polymj.34.825
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