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

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

Journal Article · Tue Jan 25 00:00:00 EST 2022 · Journal of the American Chemical Society

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

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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.

View Accepted Manuscript (DOE)

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

References (51)

Thermal Conductivity of Amorphous Materials Zhou, Wu‐Xing; Cheng, Yuan; Chen, Ke‐Qiu Advanced Functional Materials, Vol. 30, Issue 8 https://doi.org/10.1002/adfm.201903829	journal	August 2019
Probing Weak Intermolecular Interactions by Using the Invariom Approach: A Comparative Study of s -Tetrazine Nelyubina, Yulia V.; Korlyukov, Alexander A.; Lyssenko, Konstantin A. Chemistry - A European Journal, Vol. 20, Issue 23 https://doi.org/10.1002/chem.201304551	journal	April 2014
First-principles calculation of the mechanical properties of diamond nanothreads Silveira, Julian F. R. V.; Muniz, Andre R. Carbon, Vol. 113 https://doi.org/10.1016/j.carbon.2016.11.060	journal	March 2017
Mechanical properties of diamond nanothread reinforced polymer composites Zhang, L. W.; Ji, W. M.; Liew, K. M. Carbon, Vol. 132 https://doi.org/10.1016/j.carbon.2018.02.053	journal	June 2018
Carbon nanothreads from polycyclic aromatic hydrocarbon molecules Demingos, Pedro G.; Muniz, Andre R. Carbon, Vol. 140 https://doi.org/10.1016/j.carbon.2018.09.022	journal	December 2018
Thermal degradation of azobenzene dyes Nguyen, Thao L.; Saleh, Mahmoud A. Results in Chemistry, Vol. 2 https://doi.org/10.1016/j.rechem.2020.100085	journal	January 2020
CH···N Bonds and Dynamics in Isostructural Pyrimidine Polymorphs Patyk, Ewa; Podsiadło, Marcin; Katrusiak, Andrzej Crystal Growth & Design, Vol. 15, Issue 8 https://doi.org/10.1021/acs.cgd.5b00657	journal	July 2015
Discrete CH···N Bonded Patterns Modified by Temperature and Pressure in Four Pyrazine Polymorphs Patyk, Ewa; Podsiadło, Marcin; Katrusiak, Andrzej Crystal Growth & Design, Vol. 15, Issue 12 https://doi.org/10.1021/acs.cgd.5b01475	journal	November 2015
From Linear Molecular Chains to Extended Polycyclic Networks: Polymerization of Dicyanoacetylene Gou, Huiyang; Zhu, Li; Huang, Haw-Tyng Chemistry of Materials, Vol. 29, Issue 16 https://doi.org/10.1021/acs.chemmater.7b01446	journal	August 2017
Pressure-Induced Polymerization of LiN(CN) ₂ Keefer, Derek W.; Gou, Huiyang; Purdy, Andrew P. The Journal of Physical Chemistry A, Vol. 120, Issue 47 https://doi.org/10.1021/acs.jpca.6b06780	journal	November 2016
Tetracyanomethane under Pressure: Extended CN Polymers from Precursors with Built-in sp ³ Centers Keefer, Derek W.; Gou, Huiyang; Wang, Qianqian The Journal of Physical Chemistry A, Vol. 122, Issue 11 https://doi.org/10.1021/acs.jpca.7b10729	journal	February 2018
Evidence for Functionalized Carbon Nanothreads from π-Stacked, para -Disubstituted Benzenes Tang, Wan Si; Strobel, Timothy A. The Journal of Physical Chemistry C, Vol. 124, Issue 45 https://doi.org/10.1021/acs.jpcc.0c06715	journal	November 2020
Structure–Reactivity Relationship in the High-Pressure Formation of Double-Core Carbon Nanothreads from Azobenzene Crystal Romi, Sebastiano; Fanetti, Samuele; Alabarse, Frederico The Journal of Physical Chemistry C, Vol. 125, Issue 31 https://doi.org/10.1021/acs.jpcc.1c04003	journal	July 2021
Structural and Electronic Competing Mechanisms in the Formation of Amorphous Carbon Nitride by Compressing s -Triazine Citroni, Margherita; Fanetti, Samuele; Bazzicalupi, Carla The Journal of Physical Chemistry C, Vol. 119, Issue 51 https://doi.org/10.1021/acs.jpcc.5b09538	journal	December 2015
Electronic and Mechanical Properties of Partially Saturated Carbon and Carbon Nitride Nanothreads Demingos, Pedro G.; Muniz, Andre R. The Journal of Physical Chemistry C, Vol. 123, Issue 6 https://doi.org/10.1021/acs.jpcc.8b11329	journal	January 2019
High-Pressure Behavior of C ₂ I ₂ and Polymerization to a Conductive Polymer Ward, Matthew D.; Huang, Haw-Tyng; Zhu, Li The Journal of Physical Chemistry C, Vol. 123, Issue 18 https://doi.org/10.1021/acs.jpcc.8b12161	journal	March 2019
Role of Nitrogen on the Mechanical Properties of the Novel Carbon Nitride Nanothreads Zheng, Zhuoqun; Zhan, Haifei; Nie, Yihan The Journal of Physical Chemistry C, Vol. 123, Issue 47 https://doi.org/10.1021/acs.jpcc.9b07441	journal	November 2019
Evidence for Orientational Order in Nanothreads Derived from Thiophene Biswas, Arani; Ward, Matthew D.; Wang, Tao The Journal of Physical Chemistry Letters, Vol. 10, Issue 22 https://doi.org/10.1021/acs.jpclett.9b02546	journal	October 2019
Controlled Single-Crystalline Polymerization of C ₁₀ H ₈ ·C ₁₀ F ₈ under Pressure Ward, Matthew D.; Tang, Wan Si; Zhu, Li Macromolecules, Vol. 52, Issue 20 https://doi.org/10.1021/acs.macromol.9b01416	journal	September 2019
Systematic Enumeration of sp ³ Nanothreads Xu, En-shi; Lammert, Paul E.; Crespi, Vincent H. Nano Letters, Vol. 15, Issue 8 https://doi.org/10.1021/acs.nanolett.5b01343	journal	July 2015
Phonons, Localization, and Thermal Conductivity of Diamond Nanothreads and Amorphous Graphene Zhu, Taishan; Ertekin, Elif Nano Letters, Vol. 16, Issue 8 https://doi.org/10.1021/acs.nanolett.6b00557	journal	July 2016
Modifying Carbon Nitride through Extreme Phosphorus Substitution Wang, Qianqian; Gou, Huiyang; Zhu, Li ACS Materials Letters, Vol. 1, Issue 1 https://doi.org/10.1021/acsmaterialslett.9b00010	journal	March 2019
Scalable Synthesis of Crystalline One-Dimensional Carbon Nanothreads through Modest-Pressure Polymerization of Furan Huss, Steven; Wu, Sikai; Chen, Bo ACS Nano, Vol. 15, Issue 3 https://doi.org/10.1021/acsnano.0c10400	journal	January 2021
Vibrational spectra of cis-dimethyldiazene-d0, -1,1,1-d3, and -d6 Ackermann, Martin N.; Craig, Norman C.; Isberg, Ralph R. The Journal of Physical Chemistry, Vol. 83, Issue 9 https://doi.org/10.1021/j100472a017	journal	May 1979
Photolysis of reluctant azoalkanes. Effect of structure on photochemical loss of nitrogen from 2,3-diazabicyclo[2.2.2]oct-2-ene derivatives Engel, Paul S.; Nalepa, Christopher J.; Soltero, Luis R. Journal of the American Chemical Society, Vol. 105, Issue 24 https://doi.org/10.1021/ja00362a015	journal	November 1983
cis-Dimethyldiazene Ackermann, Martin N.; Craig, Norman C.; Isberg, Ralph R. Journal of the American Chemical Society, Vol. 99, Issue 5 https://doi.org/10.1021/ja00447a072	journal	March 1977
Synthesis and thermal decomposition of cis-3,4,5,6-tetrahydropyridazine-3,4-d2. Relative rates of rotation, cleavage, and closure for tetramethylene Dervan, Peter B.; Santilli, Donald S. Journal of the American Chemical Society, Vol. 102, Issue 11 https://doi.org/10.1021/ja00531a031	journal	May 1980
Pressure-Induced Polymerization of Polycyclic Arene–Perfluoroarene Cocrystals: Single Crystal X-ray Diffraction Studies, Reaction Kinetics, and Design of Columnar Hydrofluorocarbons Friedrich, Alexandra; Collings, Ines E.; Dziubek, Kamil F. Journal of the American Chemical Society, Vol. 142, Issue 44 https://doi.org/10.1021/jacs.0c09021	journal	October 2020
Perfect and Defective ¹³ C-Furan-Derived Nanothreads from Modest-Pressure Synthesis Analyzed by ¹³ C NMR Matsuura, Bryan S.; Huss, Steven; Zheng, Zhaoxi Journal of the American Chemical Society, Vol. 143, Issue 25 https://doi.org/10.1021/jacs.1c03671	journal	June 2021
Diels–Alder Reactivities of Benzene, Pyridine, and Di-, Tri-, and Tetrazines: The Roles of Geometrical Distortions and Orbital Interactions Yang, Yun-Fang; Liang, Yong; Liu, Fang Journal of the American Chemical Society, Vol. 138, Issue 5 https://doi.org/10.1021/jacs.5b12054	journal	February 2016
Mechanochemical Synthesis of Carbon Nanothread Single Crystals Li, Xiang; Baldini, Maria; Wang, Tao Journal of the American Chemical Society, Vol. 139, Issue 45 https://doi.org/10.1021/jacs.7b09311	journal	November 2017
Carbon Nitride Nanothread Crystals Derived from Pyridine Li, Xiang; Wang, Tao; Duan, Pu Journal of the American Chemical Society, Vol. 140, Issue 15 https://doi.org/10.1021/jacs.7b13247	journal	March 2018
Mechanical Properties and Defect Sensitivity of Diamond Nanothreads Roman, Ruth E.; Kwan, Kenny; Cranford, Steven W. Nano Letters, Vol. 15, Issue 3 https://doi.org/10.1021/nl5041012	journal	February 2015
Triggering dynamics of the high-pressure benzene amorphization Ciabini, Lucia; Santoro, Mario; Gorelli, Federico A. Nature Materials, Vol. 6, Issue 1 https://doi.org/10.1038/nmat1803	journal	December 2006
Benzene-derived carbon nanothreads Fitzgibbons, Thomas C.; Guthrie, Malcolm; Xu, En-shi Nature Materials, Vol. 14, Issue 1 https://doi.org/10.1038/nmat4088	journal	September 2014
From brittle to ductile: a structure dependent ductility of diamond nanothread Zhan, Haifei; Zhang, Gang; Tan, Vincent B. C. Nanoscale, Vol. 8, Issue 21 https://doi.org/10.1039/C6NR02414A	journal	January 2016
Diamond nanothread based resonators: ultrahigh sensitivity and low dissipation Duan, Ke; Li, Yijun; Li, Li Nanoscale, Vol. 10, Issue 17 https://doi.org/10.1039/C8NR00502H	journal	January 2018
First-principles study of carbon nanothreads derived from five-membered heterocyclic rings: thiophene, furan and pyrrole Demingos, Pedro G.; Balzaretti, Naira M.; Muniz, André R. Physical Chemistry Chemical Physics, Vol. 23, Issue 3 https://doi.org/10.1039/D0CP05847E	journal	January 2021
‘Sacrificial’ supramolecular assembly and pressure-induced polymerization: toward sequence-defined functionalized nanothreads Gerthoffer, Margaret C.; Wu, Sikai; Chen, Bo Chemical Science, Vol. 11, Issue 42 https://doi.org/10.1039/D0SC03904G	journal	January 2020
Synthesis of double core chromophore-functionalized nanothreads by compressing azobenzene in a diamond anvil cell Romi, Sebastiano; Fanetti, Samuele; Alabarse, Frederico Chemical Science, Vol. 12, Issue 20 https://doi.org/10.1039/D0SC06968J	journal	January 2021
Radical pathways in the thermal decomposition of pyridine and diazines: a laser pyrolysis and semi-empirical study Hore, Nathan R.; Russell, Douglas K. Journal of the Chemical Society, Perkin Transactions 2, Issue 2 https://doi.org/10.1039/a706731c	journal	January 1998
Constraining molecules at the closest approach: chemistry at high pressure Schettino, Vincenzo; Bini, Roberto Chemical Society Reviews, Vol. 36, Issue 6 https://doi.org/10.1039/b515964b	journal	January 2007
Density, freezing and molecular aggregation in pyridazine, pyridine and benzene Podsiadło, Marcin; Jakóbek, Katarzyna; Katrusiak, Andrzej CrystEngComm, Vol. 12, Issue 9 https://doi.org/10.1039/c001153c	journal	January 2010
Raman and infrared modes of hydrogenated amorphous carbon nitride Rodil, S. E.; Ferrari, A. C.; Robertson, J. Journal of Applied Physics, Vol. 89, Issue 10 https://doi.org/10.1063/1.1365076	journal	May 2001
Infrared spectroscopy of physisorbed and chemisorbed N2 in the Pt(111)(3×3)N2 structure Gustafsson, K.; Karlberg, G. S.; Andersson, S. The Journal of Chemical Physics, Vol. 127, Issue 19 https://doi.org/10.1063/1.2804869	journal	November 2007
Transformation of benzene to a polymer after static pressurization to 30 GPa Pruzan, Ph.; Chervin, J. C.; Thiéry, M. M. The Journal of Chemical Physics, Vol. 92, Issue 11 https://doi.org/10.1063/1.458278	journal	June 1990
Pressure-induced polymerization of P(CN)3 Gou, Huiyang; Yonke, Brendan L.; Epshteyn, Albert The Journal of Chemical Physics, Vol. 142, Issue 19 https://doi.org/10.1063/1.4919640	journal	May 2015
Role of excited electronic states in the high-pressure amorphization of benzene Citroni, M.; Bini, R.; Foggi, P. Proceedings of the National Academy of Sciences, Vol. 105, Issue 22 https://doi.org/10.1073/pnas.0802269105	journal	May 2008
The crystal structure of s-triazine at 5K Prasad, S. M.; Rae, A. I. M.; Hewat, A. W. Journal of Physics C: Solid State Physics, Vol. 14, Issue 31 https://doi.org/10.1088/0022-3719/14/31/001	journal	November 1981
Interpretation of infrared and Raman spectra of amorphous carbon nitrides Ferrari, A. C.; Rodil, S. E.; Robertson, J. Physical Review B, Vol. 67, Issue 15 https://doi.org/10.1103/PhysRevB.67.155306	journal	April 2003
N=N Vibrational Frequencies and Fragmentation Patterns of Substituted 1-Aryl-3,3-Dialkyl-Triazenes: Comparison with other High-Nitrogen Compounds Zimmermann, F.; Lippert, Th.; Beyer, Ch. Applied Spectroscopy, Vol. 47, Issue 7 https://doi.org/10.1366/0003702934415165	journal	July 1993

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