Chromogenic Tubular Polydiacetylenes from Topochemical Polymerization of Self-Assembled Macrocyclic Diacetylenes

Jung Moo Heo, Youngmee Kim, Seulki Han, Joonyoung F. Joung, Sang hwa Lee, Sejin Han, Jaegeun Noh, Jaeyong Kim, Sungnam Park, Haiwon Lee, Yoon Mi Choi, Young Sik Jung, Jong Man Kim

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Abstract

Tubular materials formed by self-assembly of small organic molecules find great utility in chemical and material science. Conventional tubular structures often lack stability because noncovalent molecular interactions are responsible for their conformational integrities. Herein we report the development of covalently linked chromogenic organic nanotubes which are prepared by using topochemical polymerization of self-assembled macrocyclic diacetylenes (MCDAs). Crystal structures of five MCDAs having different diameters were elucidated, and four of these substances were transformed to tubular polydiacetylenes (PDA) by UV-induced polymerization. Surprisingly, MCDA-1 was found to self-assemble in stacks with a tilt angle of 62.1°, which significantly deviates from the optimal value for polymerization of 45°. This observation suggests that geometric parameters derived using linear diacetylene (DA) models might not be strictly applicable to polymerization of MCDA systems. Blue-phase PDAs obtained by polymerization of MCDA-1 and MCDA-3 have different thermochromic and solvatochromic properties, which enable them to be utilized for colorimetric differentiation of aromatic solvents including isomeric xylenes. The observations made and information obtained in this study should enhance the understanding and design of stimulus-responsive rigid organic nanotubes.

Original languageEnglish
Pages (from-to)900-913
Number of pages14
JournalMacromolecules
Volume50
Issue number3
DOIs
Publication statusPublished - 2017 Feb 14

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ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

Heo, J. M., Kim, Y., Han, S., Joung, J. F., Lee, S. H., Han, S., Noh, J., Kim, J., Park, S., Lee, H., Choi, Y. M., Jung, Y. S., & Kim, J. M. (2017). Chromogenic Tubular Polydiacetylenes from Topochemical Polymerization of Self-Assembled Macrocyclic Diacetylenes. Macromolecules, 50(3), 900-913. https://doi.org/10.1021/acs.macromol.6b02493