Skip to main content
Journal cover image

Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes.

Publication ,  Journal Article
Strauss, MJ; Asheghali, D; Evans, AM; Li, RL; Chavez, AD; Sun, C; Becker, ML; Dichtel, WR
Published in: Angewandte Chemie (International ed. in English)
October 2019

Nanotubes assembled from macrocyclic precursors offer a unique combination of low dimensionality, structural rigidity, and distinct interior and exterior microenvironments. Usually the weak stacking energies of macrocycles limit the length and mechanical strength of the resultant nanotubes. Imine-linked macrocycles were recently found to assemble into high-aspect ratio (>103 ), lyotropic nanotubes in the presence of excess acid. Yet these harsh conditions are incompatible with many functional groups and processing methods, and lower acid loadings instead catalyze macrocycle degradation. Here we report pyridine-2,6-diimine-linked macrocycles that assemble into high-aspect ratio nanotubes in the presence of less than 1 equiv of CF3 CO2 H per macrocycle. Analysis by gel permeation chromatography and fluorescence spectroscopy revealed a cooperative self-assembly mechanism. The low acid concentrations needed to induce assembly enabled nanofibers to be obtained by touch-spinning, which exhibit higher Young's moduli (1.33 GPa) than many synthetic polymers and biological filaments. These findings represent a breakthrough in the design of inverse chromonic liquid crystals, as assembly under such mild conditions will enable the design of structurally diverse and mechanically robust nanotubes from synthetically accessible macrocycles.

Duke Scholars

Altmetric Attention Stats
Dimensions Citation Stats

Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

October 2019

Volume

58

Issue

41

Start / End Page

14708 / 14714

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Strauss, M. J., Asheghali, D., Evans, A. M., Li, R. L., Chavez, A. D., Sun, C., … Dichtel, W. R. (2019). Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes. Angewandte Chemie (International Ed. in English), 58(41), 14708–14714. https://doi.org/10.1002/anie.201907668
Strauss, Michael J., Darya Asheghali, Austin M. Evans, Rebecca L. Li, Anton D. Chavez, Chao Sun, Matthew L. Becker, and William R. Dichtel. “Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes.Angewandte Chemie (International Ed. in English) 58, no. 41 (October 2019): 14708–14. https://doi.org/10.1002/anie.201907668.
Strauss MJ, Asheghali D, Evans AM, Li RL, Chavez AD, Sun C, et al. Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes. Angewandte Chemie (International ed in English). 2019 Oct;58(41):14708–14.
Strauss, Michael J., et al. “Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes.Angewandte Chemie (International Ed. in English), vol. 58, no. 41, Oct. 2019, pp. 14708–14. Epmc, doi:10.1002/anie.201907668.
Strauss MJ, Asheghali D, Evans AM, Li RL, Chavez AD, Sun C, Becker ML, Dichtel WR. Cooperative Self-Assembly of Pyridine-2,6-Diimine-Linked Macrocycles into Mechanically Robust Nanotubes. Angewandte Chemie (International ed in English). 2019 Oct;58(41):14708–14714.
Journal cover image

Published In

Angewandte Chemie (International ed. in English)

DOI

EISSN

1521-3773

ISSN

1433-7851

Publication Date

October 2019

Volume

58

Issue

41

Start / End Page

14708 / 14714

Related Subject Headings

  • Organic Chemistry
  • 34 Chemical sciences
  • 03 Chemical Sciences