Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons

Peijie Zhang; Xingyu Tang; Yida Wang; Xuan Wang; Dexiang Gao; Yapei Li; Haiyan Zheng; Yajie Wang; Xinxin Wang; Riqiang Fu; Mingxue Tang; Kazutaka Ikeda; Ping Miao; Takanori Hattori; Asami Sano-Furukawa; Christopher A. Tulk; Jamie J. Molaison; Xiao Dong; Kuo Li; Jing Ju; Ho Kwang Mao

doi:10.1021/jacs.0c08274

Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons

Peijie Zhang, Xingyu Tang, Yida Wang, Xuan Wang, Dexiang Gao, Yapei Li, Haiyan Zheng, Yajie Wang, Xinxin Wang, Riqiang Fu, Mingxue Tang, Kazutaka Ikeda, Ping Miao, Takanori Hattori, Asami Sano-Furukawa, Christopher A. Tulk, Jamie J. Molaison, Xiao Dong, Kuo Li, Jing JuHo Kwang Mao

SNS Science Support 1

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29 Scopus citations

Abstract

Solid-state topochemical polymerization (SSTP) is a promising method to construct functional crystalline polymeric materials, but in contrast to various reactions that happen in solution, only very limited types of SSTP reactions are reported. Diels-Alder (DA) and dehydro-DA (DDA) reactions are textbook reactions for preparing six-membered rings in solution but are scarcely seen in solid-state synthesis. Here, using multiple cutting-edge techniques, we demonstrate that the solid 1,4-diphenylbutadiyne (DPB) undergoes a DDA reaction under 10-20 GPa with the phenyl as the dienophile. The crystal structure at the critical pressure shows that this reaction is "distance-selected". The distance of 3.2 Å between the phenyl and the phenylethynyl facilitates the DDA reaction, while the distances for other DDA and 1,4-addition reactions are too large to allow the bonding. The obtained products are crystalline armchair graphitic nanoribbons, and hence our studies open a new route to construct the crystalline carbon materials with atomic-scale control.

Original language	English
Pages (from-to)	17662-17669
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	142
Issue number	41
DOIs	https://doi.org/10.1021/jacs.0c08274
State	Published - Oct 14 2020

Funding

The authors acknowledge the support of the National Natural Science Foundation of China (NSFC) (Grant nos. 21771011 and 21875006). The authors also acknowledge the support of the National Key Research and Development Program of China (2019YFA0708502). This research used resources of the Advanced Light Source, which is a U.S. Department of Energy (DOE) Office of Science User Facility under Contract no. DE-AC02-05CH11231. This research used resources at the Spallation Neutron Source, a DOE Office of Science User Facility operated by the Oak Ridge National Laboratory. Neutron diffraction experiments at J-PARC were performed through the J-PARC user programs (nos. 2018B0249 and 2018BF2106). High-resolution solid-state C NMR were measured at National High Magnetic Field Laboratory supported by the U.S. NSF Cooperative Agreement DMR-1644779 and the State of Florida. The calculations were performed on the TianheII supercomputer at the Chinese National Supercomputer Center in Guangzhou. The authors thank Dr. Haijun Yang for his help in the synthesis of deuterated DPB, Dr. Xiaohuan Lin for her help in the analysis of XRD data, Dr. Xiaoge Wang and Ms. Yunling Jia for their help in the HRTEM experiments, and Dr. Hyun Hwi Lee for his help in the in situ XRD measurements performed in the 5A XRS-MS beamline at the Pohang Accelerator Laboratory (PAL). Dr. K. Li thanks Dr. T. A. Strobel for helpful discussion. 13

Funders	Funder number
State of Florida
National Science Foundation	DMR-1644779
National Science Foundation
U.S. Department of Energy
Office of Science	DE-AC02-05CH11231
Office of Science
National Natural Science Foundation of China	21875006, 21771011
National Natural Science Foundation of China
National Key Research and Development Program of China	2019YFA0708502
National Key Research and Development Program of China

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Zhang, P., Tang, X., Wang, Y., Wang, X., Gao, D., Li, Y., Zheng, H., Wang, Y., Wang, X., Fu, R., Tang, M., Ikeda, K., Miao, P., Hattori, T., Sano-Furukawa, A., Tulk, C. A., Molaison, J. J., Dong, X., Li, K., ... Mao, H. K. (2020). Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons. Journal of the American Chemical Society, 142(41), 17662-17669. https://doi.org/10.1021/jacs.0c08274

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title = "Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons",

abstract = "Solid-state topochemical polymerization (SSTP) is a promising method to construct functional crystalline polymeric materials, but in contrast to various reactions that happen in solution, only very limited types of SSTP reactions are reported. Diels-Alder (DA) and dehydro-DA (DDA) reactions are textbook reactions for preparing six-membered rings in solution but are scarcely seen in solid-state synthesis. Here, using multiple cutting-edge techniques, we demonstrate that the solid 1,4-diphenylbutadiyne (DPB) undergoes a DDA reaction under 10-20 GPa with the phenyl as the dienophile. The crystal structure at the critical pressure shows that this reaction is {"}distance-selected{"}. The distance of 3.2 {\AA} between the phenyl and the phenylethynyl facilitates the DDA reaction, while the distances for other DDA and 1,4-addition reactions are too large to allow the bonding. The obtained products are crystalline armchair graphitic nanoribbons, and hence our studies open a new route to construct the crystalline carbon materials with atomic-scale control.",

author = "Peijie Zhang and Xingyu Tang and Yida Wang and Xuan Wang and Dexiang Gao and Yapei Li and Haiyan Zheng and Yajie Wang and Xinxin Wang and Riqiang Fu and Mingxue Tang and Kazutaka Ikeda and Ping Miao and Takanori Hattori and Asami Sano-Furukawa and Tulk, {Christopher A.} and Molaison, {Jamie J.} and Xiao Dong and Kuo Li and Jing Ju and Mao, {Ho Kwang}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = oct,

day = "14",

doi = "10.1021/jacs.0c08274",

language = "English",

volume = "142",

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Zhang, P, Tang, X, Wang, Y, Wang, X, Gao, D, Li, Y, Zheng, H, Wang, Y, Wang, X, Fu, R, Tang, M, Ikeda, K, Miao, P, Hattori, T, Sano-Furukawa, A, Tulk, CA, Molaison, JJ, Dong, X, Li, K, Ju, J & Mao, HK 2020, 'Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons', Journal of the American Chemical Society, vol. 142, no. 41, pp. 17662-17669. https://doi.org/10.1021/jacs.0c08274

TY - JOUR

T1 - Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons

AU - Zhang, Peijie

AU - Tang, Xingyu

AU - Wang, Yida

AU - Wang, Xuan

AU - Gao, Dexiang

AU - Li, Yapei

AU - Zheng, Haiyan

AU - Wang, Yajie

AU - Wang, Xinxin

AU - Fu, Riqiang

AU - Tang, Mingxue

AU - Ikeda, Kazutaka

AU - Miao, Ping

AU - Hattori, Takanori

AU - Sano-Furukawa, Asami

AU - Tulk, Christopher A.

AU - Molaison, Jamie J.

AU - Dong, Xiao

AU - Li, Kuo

AU - Ju, Jing

AU - Mao, Ho Kwang

PY - 2020/10/14

Y1 - 2020/10/14

N2 - Solid-state topochemical polymerization (SSTP) is a promising method to construct functional crystalline polymeric materials, but in contrast to various reactions that happen in solution, only very limited types of SSTP reactions are reported. Diels-Alder (DA) and dehydro-DA (DDA) reactions are textbook reactions for preparing six-membered rings in solution but are scarcely seen in solid-state synthesis. Here, using multiple cutting-edge techniques, we demonstrate that the solid 1,4-diphenylbutadiyne (DPB) undergoes a DDA reaction under 10-20 GPa with the phenyl as the dienophile. The crystal structure at the critical pressure shows that this reaction is "distance-selected". The distance of 3.2 Å between the phenyl and the phenylethynyl facilitates the DDA reaction, while the distances for other DDA and 1,4-addition reactions are too large to allow the bonding. The obtained products are crystalline armchair graphitic nanoribbons, and hence our studies open a new route to construct the crystalline carbon materials with atomic-scale control.

AB - Solid-state topochemical polymerization (SSTP) is a promising method to construct functional crystalline polymeric materials, but in contrast to various reactions that happen in solution, only very limited types of SSTP reactions are reported. Diels-Alder (DA) and dehydro-DA (DDA) reactions are textbook reactions for preparing six-membered rings in solution but are scarcely seen in solid-state synthesis. Here, using multiple cutting-edge techniques, we demonstrate that the solid 1,4-diphenylbutadiyne (DPB) undergoes a DDA reaction under 10-20 GPa with the phenyl as the dienophile. The crystal structure at the critical pressure shows that this reaction is "distance-selected". The distance of 3.2 Å between the phenyl and the phenylethynyl facilitates the DDA reaction, while the distances for other DDA and 1,4-addition reactions are too large to allow the bonding. The obtained products are crystalline armchair graphitic nanoribbons, and hence our studies open a new route to construct the crystalline carbon materials with atomic-scale control.

UR - http://www.scopus.com/inward/record.url?scp=85092945175&partnerID=8YFLogxK

U2 - 10.1021/jacs.0c08274

DO - 10.1021/jacs.0c08274

M3 - Article

C2 - 32900188

AN - SCOPUS:85092945175

SN - 0002-7863

VL - 142

SP - 17662

EP - 17669

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 41

ER -

Distance-Selected Topochemical Dehydro-Diels-Alder Reaction of 1,4-Diphenylbutadiyne toward Crystalline Graphitic Nanoribbons

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