Solid-State Pathway Control via Reaction-Directing Heteroatoms: Ordered Pyridazine Nanothreads through Selective Cycloaddition

Samuel G. Dunning, Li Zhu, Bo Chen, Stella Chariton, Vitali B. Prakapenka, Maddury Somayazulu, Timothy A. Strobel

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Nanothreads are one-dimensional nanomaterials composed of a primarily sp3 hydrocarbon backbone, typically formed through the compression of small molecules to high pressures. Although nanothreads have been synthesized from a range of precursors, controlling reaction pathways to produce atomically precise materials remains a difficult challenge. Here, we show how heteroatoms within precursors can serve as "thread-directing"groups by selecting for specific cycloaddition reaction pathways. By using a less-reactive diazine group within a six-membered aromatic ring, we successfully predict and synthesize the first carbon nanothread material derived from pyridazine (1,2-diazine, C4H4N2). Compared with previous nanothreads, the synthesized polypyridazine, shows a predominantly uniform chemical structure with exceptional long-range order, allowing for structural characterization using vibrational spectroscopy and X-ray diffraction. The results demonstrate how thread-directing groups can be used for reaction pathway control and the formation of chemically precise nanothreads with a high degree of structural order.

Original languageEnglish (US)
Pages (from-to)2073-2078
Number of pages6
JournalJournal of the American Chemical Society
Volume144
Issue number5
DOIs
StatePublished - Feb 9 2022
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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