Triggering dynamics of acetylene topochemical polymerization

Tang Xingyu; Dong Xiao; Zhang Chunfang; Li Kuo; Zheng Haiyan; Mao Ho-kwang

doi:10.1063/5.0151609

Volume 8 Issue 5

Sep. 2023

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Tang Xingyu, Dong Xiao, Zhang Chunfang, Li Kuo, Zheng Haiyan, Mao Ho-kwang. Triggering dynamics of acetylene topochemical polymerization[J]. Matter and Radiation at Extremes, 2023, 8(5): 058402. doi: 10.1063/5.0151609

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Tang Xingyu, Dong Xiao, Zhang Chunfang, Li Kuo, Zheng Haiyan, Mao Ho-kwang. Triggering dynamics of acetylene topochemical polymerization[J]. Matter and Radiation at Extremes, 2023, 8(5): 058402. doi: 10.1063/5.0151609

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Triggering dynamics of acetylene topochemical polymerization

doi: 10.1063/5.0151609

Tang Xingyu^1
,,
Dong Xiao^{2
,
,
,},
Zhang Chunfang^3
,,
Li Kuo^{1
,
,
,},
Zheng Haiyan^1
,,
Mao Ho-kwang^1
,

1.
Center for High Pressure Science and Technology Advanced Research, Beijing 100193, People’s Republic of China
2.
Key Laboratory of Weak-Light Nonlinear Photonics, School of Physics, Nankai University, Tianjin 300071, People’s Republic of China
3.
College of Chemistry and Materials Science, Hebei University, Baoding 071002, People’s Republic of China

More Information

Corresponding author: a)Authors to whom correspondence should be addressed: likuo@hpstar.ac.cn and xiao.dong@nankai.edu.cn
Received Date: 2023-03-23
Accepted Date: 2023-07-02

Available Online: 2023-09-01

Publish Date: 2023-09-01

Abstract

Abstract

Topochemical reactions are a promising method to obtain crystalline polymeric materials with distance-determined regio- or stereoselectivity. It has been concluded on an empirical basis that the closest intermolecular C⋯C distance in crystals of alkynes, d_(C⋯C)min, should reach a threshold of ∼3 Å for bonding to occur at room temperature. To understand this empirical threshold, we study here the polymerization of acetylene in the crystalline state under high pressure by calculating the structural geometry, vibrational modes, and reaction profile. We find d_(C⋯C)min to be the sum of an intrinsic threshold of 2.3 Å and a thermal displacement of 0.8 Å (at room temperature). Molecules at the empirical threshold move via several phonon modes to reach the intrinsic threshold, at which the intermolecular electronic interaction is sharply enhanced and bonding commences. A distance–vibration-based reaction picture is thus demonstrated, which provides a basis for the prediction and design of topochemical reactions, as well as an enhanced understanding of the bonding process in solids.

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References(26)

References

[1]	K. Hema, A. Ravi, C. Raju, J. R. Pathan, R. Rai, and K. M. Sureshan, “Topochemical polymerizations for the solid-state synthesis of organic polymers,” Chem. Soc. Rev. 50, 4062 (2021).10.1039/d0cs00840k
[2]	K. Biradha and R. Santra, “Crystal engineering of topochemical solid state reactions,” Chem. Soc. Rev. 42, 950 (2013).10.1039/c2cs35343a
[3]	C. Sauteret, J. P. Hermann, R. Frey, F. Pradère, J. Ducuing, R. H. Baughman, and R. R. Chance, “Optical nonlinearities in one-dimensional-conjugated polymer,” Phys. Rev. Lett. 36, 956 (1976).10.1103/physrevlett.36.956
[4]	T. Kato, M. Yasumatsu, C. Origuchi, K. Tsutsui, Y. Ueda, and C. Adachi, “High carrier mobility of 3.8 cm2 V−1 s−1 in polydiacetylene thin films polymerized by electron beam irradiation,” Appl. Phys. Express 4, 091601 (2011).10.1143/apex.4.091601
[5]	X. Wang, X. Tang, P. Zhang, Y. Wang, D. Gao, J. Liu, K. Hui, Y. Wang, X. Dong, T. Hattori, A. Sano-Furukawa, K. Ikeda, P. Miao, X. Lin, M. Tang, Z. Zuo, H. Zheng, K. Li, and H.-k. Mao, “Crystalline fully carboxylated polyacetylene obtained under high pressure as a Li-ion battery anode material,” J. Phys. Chem.Lett. 12, 12055 (2021).10.1021/acs.jpclett.1c03734
[6]	L. Dou, Y. Zheng, X. Shen, G. Wu, K. Fields, W. C. Hsu, H. Zhou, Y. Yang, and F. Wudl, “Single-crystal linear polymers through visible light-triggered topochemical quantitative polymerization,” Science 343, 272 (2014).10.1126/science.1245875
[7]	J. W. Lauher, F. W. Fowler, and N. S. Goroff, “Single-crystal-to-single-crystal topochemical polymerizations by design,” Acc. Chem. Res. 41, 1215 (2008).10.1021/ar8001427
[8]	G. M. J. Schmidt, “Topochemistry. Part III. The crystal chemistry of some trans-cinnamic acids,” J. Chem. Soc. 1964, 2014.10.1039/JR9640002014
[9]	K. Hema and K. M. Sureshan, “Topochemical azide–alkyne cycloaddition reaction,” Acc. Chem. Res. 52, 3149 (2019).10.1021/acs.accounts.9b00398
[10]	M. J. Kory, M. Wörle, T. Weber, P. Payamyar, S. W. van de Poll, J. Dshemuchadse, N. Trapp, and A. D. Schlüter, “Gram-scale synthesis of two-dimensional polymer crystals and their structure analysis by X-ray diffraction,” Nat. Chem. 6, 779 (2014).10.1038/nchem.2007
[11]	J. Xiao, M. Yang, J. W. Lauher, and F. W. Fowler, “A supramolecular solution to a long-standing problem: The 1,6-polymerization of a triacetylene,” Angew. Chem., Int. Ed. 39, 2132 (2000).10.1002/1521-3773(20000616)39:12<2132::aid-anie2132>3.0.co;2-8
[12]	P. Kissel, R. Erni, W. B. Schweizer, M. D. Rossell, B. T. King, T. Bauer, S. Götzinger, A. D. Schlüter, and J. Sakamoto, “A two-dimensional polymer prepared by organic synthesis,” Nat. Chem. 4, 287 (2012).10.1038/nchem.1265
[13]	W. L. Dilling, “Organic photochemistry. XVII. Polymerization of unsaturated compounds by photocycloaddition reactions,” Chem. Rev. 83, 1 (1983).10.1021/cr00053a001
[14]	M. Hasegawa, “Photopolymerization of diolefin crystals,” Chem. Rev. 83, 507 (1983).10.1021/cr00057a001
[15]	C.-S. Yoo, “Chemistry under extreme conditions: Pressure evolution of chemical bonding and structure in dense solids,” Matter Radiat. Extremes 5, 018202 (2020).10.1063/1.5127897
[16]	F. Li, J. Xu, Y. Wang, H. Zheng, and K. Li, “Pressure-induced polymerization: Addition and condensation reactions,” Molecules 26, 7581 (2021).10.3390/molecules26247581
[17]	J. Sun, X. Dong, Y. Wang, K. Li, H. Zheng, L. Wang, G. D. Cody, C. A. Tulk, J. J. Molaison, X. Lin, Y. Meng, C. Jin, and H.-k. Mao, “Pressure-induced polymerization of acetylene: Structure-directed stereoselectivity and a possible route to graphene,” Angew. Chem., Int. Ed. 56, 6553 (2017).10.1002/anie.201702685
[18]	J. Han, X. Tang, Y. Wang, Y. Wang, Y. Han, X. Lin, X. Dong, H. H. Lee, H. Zheng, K. Li, and H.-k. Mao, “Pressure-induced polymerization of monosodium acetylide: A radical reaction initiated topochemically,” J. Phys. Chem. C 123, 30746 (2019).10.1021/acs.jpcc.9b09698
[19]	G. Qi, S. Song, Z. Deng, D. Huang, F. Chen, B. Yan, H. Gou, Q. Zhang, and Y. Wang, “Pressure-induced topochemical polymerization toward advanced energetic materials,” CCS Chem (published online) (2022).10.31635/ccschem.022.202202249
[20]	L. Ciabini, M. Santoro, F. A. Gorelli, R. Bini, V. Schettino, and S. Raugei, “Triggering dynamics of the high-pressure benzene amorphization,” Nat. Mater. 6, 39 (2007).10.1038/nmat1803
[21]	Y. Wang, X. Dong, X. Tang, H. Zheng, K. Li, X. Lin, L. Fang, G. Sun, X. Chen, L. Xie, C. L. Bull, N. P. Funnell, T. Hattori, A. Sano-Furukawa, J. Chen, D. K. Hensley, G. D. Cody, Y. Ren, H. H. Lee, and H.-k. Mao, “Pressure-induced Diels–Alder reactions in C6H6-C6F6 cocrystal towards graphane structure,” Angew. Chem., Int. Ed. 58, 1468 (2000).10.1002/anie.201813120
[22]	P. Zhang, X. Tang, Y. Wang, X. Wang, D. Gao, Y. Li, H. Zheng, Y. Wang, X. Wang, R. Fu, M. Tang, K. Ikeda, P. Miao, T. Hattori, A. Sano-Furukawa, C. A. Tulk, J. J. Molaison, X. Dong, K. Li, J. Ju, and H.-k. Mao, “Distance-selected topochemical dehydro-Diels–Alder reaction of 1,4-diphenylbutadiyne toward crystalline graphitic nanoribbons,” J. Am. Chem. Soc. 142, 17662 (2020).10.1021/jacs.0c08274
[23]	Y. Li, X. Tang, P. Zhang, Y. Wang, X. Yang, X. Wang, K. Li, Y. Wang, N. Wu, M. Tang, J. Xiang, X. Lin, H. H. Lee, X. Dong, H. Zheng, and H.-k. Mao, “Scalable high-pressure synthesis of sp2–sp3 carbon nanoribbon via [4 + 2] polymerization of 1,3,5-triethynylbenzene,” J. Phys. Chem. Lett. 12, 7140 (2021).10.1021/acs.jpclett.1c01945
[24]	H. Shirakawa, E. J. Louis, A. G. MacDiarmid, C. K. Chiang, and A. J. Heeger, “Synthesis of electrically conducting organic polymers: Halogen derivatives of polyacetylene, (CH)x,” J. Chem. Soc. Chem. Commun. 1977, 578.10.1039/c39770000578
[25]	M. Sakashita, H. Yamawaki, and K. Aoki, “FT-IR study of the solid state polymerization of acetylene under pressure,” J. Phys. Chem. 100, 9943 (1996).10.1021/jp960306l
[26]	C. C. Trout and J. V. Badding, “Solid state polymerization of acetylene at high pressure and low temperature,” J. Phys. Chem. A 104, 8142 (2000).10.1021/jp000198+