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

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

doi:10.1021/jacs.1c12143

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

Journal Article · 24 January 2022 · Journal of the American Chemical Society

DOI: https://doi.org/10.1021/jacs.1c12143 · OSTI ID:1869164

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^[3]; Prakapenka, Vitali B. ^[3];

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Carnegie Inst. of Science, Washington, DC (United States)
Donostia International Physics Center (DIPC), San Sebastian (Spain); Basque Foundation for Science, Bilbao (Spain)
Univ. of Chicago, IL (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)

Nanothreads are one-dimensional nanomaterials comprised of a primarily sp³ hydrocarbon backbone. They are typically formed through cycloaddition reactions induced by compression of small molecules to high pressures. Although nanothreads have been synthesized from a range of small molecule precursors (e.g., benzene, pyridine, aniline), the ability to control reaction pathways to produce atomically precise nanothreads with distinct chemical structures remains a difficult challenge. In this study, we show how heteroatoms incorporated within starting 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 precise reaction pathway control and the formation of chemically precise nanothreads with a high degree of structural order.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: US Army Research Office; USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division

Grant/Contract Number:: AC02-06CH11357; FG02-94ER14466

OSTI ID:: 1869164

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 5 Vol. 144; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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