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Dual Trapping of a Metastable Planarized Triarylborane π-System Based on Folding and Lewis Acid–Base Complexation for Seeded Polymerization
- Source :
- Journal of the American Chemical Society; February 2021, Vol. 143 Issue: 7 p2953-2961, 9p
- Publication Year :
- 2021
-
Abstract
- We report the kinetically controlled supramolecular polymerization of boron-containing π-conjugated molecules, which was enabled by a seeding method based on dual trapping of a metastable state by synergistic intramolecular hydrogen bonding and Lewis acid-based complexation. Planarized triarylborane-based 1, which bears a diamide chain with chiral alkyl groups, was synthesized. Upon cooling, the solution of monomer 1afforded a supramolecular polymerization in a cooperative manner to form helical supramolecular nanostructures with intense J-type aggregate emission. In the presence of pyridine, the triarylborane moiety formed a Lewis acid–base complex, which enhances the stabilization of the metastable monomeric state. An assembly incompetent structure with a folded diamide chain conformation and a pyridine moiety axially coordinated to the boron atom is responsible for slowing the spontaneous aggregation. The seeding method was successfully applied to the solution to produce homogeneous nanofibers even at a high (millimolar-level) concentration. This unprecedented kinetic control via dual trapping provides an effective method to achieve seed-initiated polymerization under concentrated conditions.
Details
- Language :
- English
- ISSN :
- 00027863 and 15205126
- Volume :
- 143
- Issue :
- 7
- Database :
- Supplemental Index
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Periodical
- Accession number :
- ejs55636205
- Full Text :
- https://doi.org/10.1021/jacs.0c13353