Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation
Abstract
The incorporation of large π-conjugated ligands into metal–organic frameworks (MOFs) can present interesting photophysical and electrochemical properties into the framework. However, these effects are often hindered by the strong π–π interaction and the low solubility of the arylated ligands. Herein, we report the synthesis of a porous zirconium-based MOF, Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(HCHC) (PCN-136, HCHC = hexakis(4-carboxyphenyl)hexabenzocoronene), which is composed of a hexacarboxylate linker with a π-conjugated hexabenzocoronene moiety. Direct assembly of the Zr4+ metal centers and the HCHC ligands was unsuccessful due to the low solubility and the unfavorable conformation of the arylated HCHC ligand. Hence, PCN-136 was obtained from aromatization-driven postsynthetic annulation of the hexaphenylbenzene fragment in a preformed framework (pbz-MOF-1) to avoid π–π stacking. This postsynthetic modification was done through a single-crystal-to-single-crystal transformation and was clearly observable utilizing single -crystal X-ray crystallography. The formation of large π-conjugated systems on the organic linker dramatically enhanced the photoresponsive properties of PCN-136. With isolated hexabenzocoronene moieties as photosensitizers and Zr–oxo clusters as catalytic sites, PCN-136 was employed as an inherent photocatalytic system for CO2 reduction under visible-light irradiation, which showed increased activity compared with pbz-MOF-1.
- Authors:
-
- Texas A & M Univ., College Station, TX (United States); Jilin Univ., Changchun (China)
- Texas A & M Univ., College Station, TX (United States); Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
- Nanjing Univ. (China)
- Texas A & M Univ., College Station, TX (United States)
- Northeast Normal Univ., Changchun (China)
- King Saud Univ., Riyadh (Saudi Arabia)
- Texas A & M Univ., College Station, TX (United States); King Saud Univ., Riyadh (Saudi Arabia)
- Publication Date:
- Research Org.:
- Univ. of California, Berkeley, CA (United States). Energy Frontier Research Center (EFRC) Center for Gas Separations Relevant to Clean Energy Technologies (CGS); Texas A & M Univ., College Station, TX (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Fossil Energy (FE)
- OSTI Identifier:
- 1566593
- Grant/Contract Number:
- FE0026472; SC0001015
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 141; Journal Issue: 5; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Qin, Jun-Sheng, Yuan, Shuai, Zhang, Lei, Li, Bao, Du, Dong-Ying, Huang, Ning, Guan, Wei, Drake, Hannah F., Pang, Jiandong, Lan, Ya-Qian, Alsalme, Ali, and Zhou, Hong-Cai. Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation. United States: N. p., 2019.
Web. doi:10.1021/jacs.8b11042.
Qin, Jun-Sheng, Yuan, Shuai, Zhang, Lei, Li, Bao, Du, Dong-Ying, Huang, Ning, Guan, Wei, Drake, Hannah F., Pang, Jiandong, Lan, Ya-Qian, Alsalme, Ali, & Zhou, Hong-Cai. Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation. United States. https://doi.org/10.1021/jacs.8b11042
Qin, Jun-Sheng, Yuan, Shuai, Zhang, Lei, Li, Bao, Du, Dong-Ying, Huang, Ning, Guan, Wei, Drake, Hannah F., Pang, Jiandong, Lan, Ya-Qian, Alsalme, Ali, and Zhou, Hong-Cai. Wed .
"Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation". United States. https://doi.org/10.1021/jacs.8b11042. https://www.osti.gov/servlets/purl/1566593.
@article{osti_1566593,
title = {Creating Well-Defined Hexabenzocoronene in Zirconium Metal–Organic Framework by Postsynthetic Annulation},
author = {Qin, Jun-Sheng and Yuan, Shuai and Zhang, Lei and Li, Bao and Du, Dong-Ying and Huang, Ning and Guan, Wei and Drake, Hannah F. and Pang, Jiandong and Lan, Ya-Qian and Alsalme, Ali and Zhou, Hong-Cai},
abstractNote = {The incorporation of large π-conjugated ligands into metal–organic frameworks (MOFs) can present interesting photophysical and electrochemical properties into the framework. However, these effects are often hindered by the strong π–π interaction and the low solubility of the arylated ligands. Herein, we report the synthesis of a porous zirconium-based MOF, Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(HCHC) (PCN-136, HCHC = hexakis(4-carboxyphenyl)hexabenzocoronene), which is composed of a hexacarboxylate linker with a π-conjugated hexabenzocoronene moiety. Direct assembly of the Zr4+ metal centers and the HCHC ligands was unsuccessful due to the low solubility and the unfavorable conformation of the arylated HCHC ligand. Hence, PCN-136 was obtained from aromatization-driven postsynthetic annulation of the hexaphenylbenzene fragment in a preformed framework (pbz-MOF-1) to avoid π–π stacking. This postsynthetic modification was done through a single-crystal-to-single-crystal transformation and was clearly observable utilizing single -crystal X-ray crystallography. The formation of large π-conjugated systems on the organic linker dramatically enhanced the photoresponsive properties of PCN-136. With isolated hexabenzocoronene moieties as photosensitizers and Zr–oxo clusters as catalytic sites, PCN-136 was employed as an inherent photocatalytic system for CO2 reduction under visible-light irradiation, which showed increased activity compared with pbz-MOF-1.},
doi = {10.1021/jacs.8b11042},
journal = {Journal of the American Chemical Society},
number = 5,
volume = 141,
place = {United States},
year = {2019},
month = {1}
}
Web of Science
Works referenced in this record:
Artificial Photosynthesis: Solar Splitting of Water to Hydrogen and Oxygen
journal, March 1995
- Bard, Allen J.; Fox, Marye Anne
- Accounts of Chemical Research, Vol. 28, Issue 3
Direct splitting of water under visible light irradiation with an oxide semiconductor photocatalyst
journal, December 2001
- Zou, Zhigang; Ye, Jinhua; Sayama, Kazuhiro
- Nature, Vol. 414, Issue 6864
Advanced Nanoarchitectures for Solar Photocatalytic Applications
journal, November 2011
- Kubacka, Anna; Fernández-García, Marcos; Colón, Gerardo
- Chemical Reviews, Vol. 112, Issue 3
Engineering coordination polymers for photocatalysis
journal, April 2016
- Zhang, Huabin; Liu, Guigao; Shi, Li
- Nano Energy, Vol. 22
Photoelectrocatalytic reduction of carbon dioxide in aqueous suspensions of semiconductor powders
journal, February 1979
- Inoue, Tooru; Fujishima, Akira; Konishi, Satoshi
- Nature, Vol. 277, Issue 5698
Effect of Surface Structures on Photocatalytic CO 2 Reduction Using Quantized CdS Nanocrystallites 1
journal, October 1997
- Fujiwara, Hiroaki; Hosokawa, Hiroji; Murakoshi, Kei
- The Journal of Physical Chemistry B, Vol. 101, Issue 41
Photoreduction of carbon dioxide using chalcogenide semiconductor microcrystals
journal, February 1995
- Inoue, Hiroshi; Moriwaki, Hiroshi; Maeda, Kataro
- Journal of Photochemistry and Photobiology A: Chemistry, Vol. 86, Issue 1-3
Introduction to Metal–Organic Frameworks
journal, September 2011
- Zhou, Hong-Cai; Long, Jeffrey R.; Yaghi, Omar M.
- Chemical Reviews, Vol. 112, Issue 2, p. 673-674
Metal–Organic Frameworks (MOFs)
journal, January 2014
- Zhou, Hong-Cai “Joe”; Kitagawa, Susumu
- Chem. Soc. Rev., Vol. 43, Issue 16
Metal–organic frameworks for artificial photosynthesis and photocatalysis
journal, January 2014
- Zhang, Teng; Lin, Wenbin
- Chem. Soc. Rev., Vol. 43, Issue 16
Stable metal–organic frameworks as a host platform for catalysis and biomimetics
journal, January 2018
- Qin, Jun-Sheng; Yuan, Shuai; Lollar, Christina
- Chemical Communications, Vol. 54, Issue 34
MOFs-Based Heterogeneous Catalysts: New Opportunities for Energy-Related CO 2 Conversion
journal, October 2018
- Lei, Zhendong; Xue, Yuancheng; Chen, Wenqian
- Advanced Energy Materials, Vol. 8, Issue 32
Carbon Dioxide Capture in Metal–Organic Frameworks
journal, September 2011
- Sumida, Kenji; Rogow, David L.; Mason, Jarad A.
- Chemical Reviews, Vol. 112, Issue 2, p. 724-781
Self-Accelerating CO Sorption in a Soft Nanoporous Crystal
journal, December 2013
- Sato, H.; Kosaka, W.; Matsuda, R.
- Science, Vol. 343, Issue 6167
Methane storage in metal–organic frameworks
journal, January 2014
- He, Yabing; Zhou, Wei; Qian, Guodong
- Chem. Soc. Rev., Vol. 43, Issue 16
Recent advances in porous polyoxometalate-based metal–organic framework materials
journal, January 2014
- Du, Dong-Ying; Qin, Jun-Sheng; Li, Shun-Li
- Chem. Soc. Rev., Vol. 43, Issue 13
Luminescent metal–organic frameworks for chemical sensing and explosive detection
journal, January 2014
- Hu, Zhichao; Deibert, Benjamin J.; Li, Jing
- Chem. Soc. Rev., Vol. 43, Issue 16
Ultrastable Polymolybdate-Based Metal–Organic Frameworks as Highly Active Electrocatalysts for Hydrogen Generation from Water
journal, May 2015
- Qin, Jun-Sheng; Du, Dong-Ying; Guan, Wei
- Journal of the American Chemical Society, Vol. 137, Issue 22
Postsynthetic Tuning of Metal–Organic Frameworks for Targeted Applications
journal, February 2017
- Islamoglu, Timur; Goswami, Subhadip; Li, Zhanyong
- Accounts of Chemical Research, Vol. 50, Issue 4
Metal–organic and covalent organic frameworks as single-site catalysts
journal, January 2017
- Rogge, S. M. J.; Bavykina, A.; Hajek, J.
- Chemical Society Reviews, Vol. 46, Issue 11
Derivation and Decoration of Nets with Trigonal-Prismatic Nodes: A Unique Route to Reticular Synthesis of Metal–Organic Frameworks
journal, January 2016
- Qin, Jun-Sheng; Du, Dong-Ying; Li, Mian
- Journal of the American Chemical Society, Vol. 138, Issue 16
Design and synthesis of multifunctional metal–organic zeolites
journal, January 2018
- Tan, Yan-Xi; Wang, Fei; Zhang, Jian
- Chemical Society Reviews, Vol. 47, Issue 6
Doping Metal–Organic Frameworks for Water Oxidation, Carbon Dioxide Reduction, and Organic Photocatalysis
journal, August 2011
- Wang, Cheng; Xie, Zhigang; deKrafft, Kathryn E.
- Journal of the American Chemical Society, Vol. 133, Issue 34, p. 13445-13454
Studies on Photocatalytic CO 2 Reduction over NH 2 -Uio-66(Zr) and Its Derivatives: Towards a Better Understanding of Photocatalysis on Metal-Organic Frameworks
journal, September 2013
- Sun, Dengrong; Fu, Yanghe; Liu, Wenjun
- Chemistry - A European Journal, Vol. 19, Issue 42
Visible-Light Photoreduction of CO 2 in a Metal–Organic Framework: Boosting Electron–Hole Separation via Electron Trap States
journal, October 2015
- Xu, Hai-Qun; Hu, Jiahua; Wang, Dengke
- Journal of the American Chemical Society, Vol. 137, Issue 42
Photocatalytic CO 2 reduction by a mixed metal (Zr/Ti), mixed ligand metal–organic framework under visible light irradiation
journal, January 2015
- Lee, Yeob; Kim, Sangjun; Kang, Jeung Ku
- Chemical Communications, Vol. 51, Issue 26
Highly efficient visible-light-driven CO 2 reduction to formate by a new anthracene-based zirconium MOF via dual catalytic routes
journal, January 2016
- Chen, Dashu; Xing, Hongzhu; Wang, Chungang
- Journal of Materials Chemistry A, Vol. 4, Issue 7
Postsynthetic modification of metal–organic frameworks—a progress report
journal, January 2011
- Tanabe, Kristine K.; Cohen, Seth M.
- Chem. Soc. Rev., Vol. 40, Issue 2
Beyond post-synthesis modification: evolution of metal–organic frameworks via building block replacement
journal, January 2014
- Deria, Pravas; Mondloch, Joseph E.; Karagiaridi, Olga
- Chem. Soc. Rev., Vol. 43, Issue 16
Stable Metal–Organic Frameworks with Group 4 Metals: Current Status and Trends
journal, February 2018
- Yuan, Shuai; Qin, Jun-Sheng; Lollar, Christina T.
- ACS Central Science, Vol. 4, Issue 4
Graphenes as Potential Material for Electronics
journal, March 2007
- Wu, Jishan; Pisula, Wojciech; Müllen, Klaus
- Chemical Reviews, Vol. 107, Issue 3
Graphitic Carbon Nitride (g-C 3 N 4 )-Based Photocatalysts for Artificial Photosynthesis and Environmental Remediation: Are We a Step Closer To Achieving Sustainability?
journal, May 2016
- Ong, Wee-Jun; Tan, Lling-Lling; Ng, Yun Hau
- Chemical Reviews, Vol. 116, Issue 12
New advances in nanographene chemistry
journal, January 2015
- Narita, Akimitsu; Wang, Xiao-Ye; Feng, Xinliang
- Chemical Society Reviews, Vol. 44, Issue 18
Donor–acceptor conjugated ladder polymer via aromatization-driven thermodynamic annulation
journal, January 2018
- Lee, Jongbok; Kalin, Alexander J.; Wang, Chenxu
- Polymer Chemistry, Vol. 9, Issue 13
Aromatizing Olefin Metathesis by Ligand Isolation inside a Metal– Organic Framework
journal, September 2013
- Vermeulen, Nicolaas A.; Karagiaridi, Olga; Sarjeant, Amy A.
- Journal of the American Chemical Society, Vol. 135, Issue 40
Reticular Chemistry at Its Best: Directed Assembly of Hexagonal Building Units into the Awaited Metal-Organic Framework with the Intricate Polybenzene Topology, pbz-MOF
journal, September 2016
- Alezi, Dalal; Spanopoulos, Ioannis; Tsangarakis, Constantinos
- Journal of the American Chemical Society, Vol. 138, Issue 39
Abspaltung aromatisch gebundenen Wasserstoffs und Verknüpfung aromatischer Kerne durch Aluminiumchlorid
journal, January 1912
- Scholl, Roland; Seer, Christian
- Justus Liebig's Annalen der Chemie, Vol. 394, Issue 2
The Versatile Synthesis and Self-Assembly of Star-Type Hexabenzocoronenes
journal, November 2003
- Wu, Jishan; Watson, Mark D.; Müllen, Klaus
- Angewandte Chemie International Edition, Vol. 42, Issue 43
Single-crystal structure validation with the program PLATON
journal, January 2003
- Spek, A. L.
- Journal of Applied Crystallography, Vol. 36, Issue 1, p. 7-13
Synthesis and sorption properties of hexa-(peri)-hexabenzocoronene-based porous organic polymers
journal, January 2014
- Thompson, Christina M.; Li, Fei; Smaldone, Ronald A.
- Chem. Commun., Vol. 50, Issue 46
Hexaphenylbenzene and hexabenzocoronene-based porous polymers for the adsorption of volatile organic compounds
journal, January 2016
- Karunathilake, Arosha A. K.; Chang, James; Thompson, Christina M.
- RSC Advances, Vol. 6, Issue 70
Methane Adsorption in Metal–Organic Frameworks Containing Nanographene Linkers: A Computational Study
journal, July 2014
- Bichoutskaia, Elena; Suyetin, Mikhail; Bound, Michelle
- The Journal of Physical Chemistry C, Vol. 118, Issue 29
A polymeric-semiconductor–metal-complex hybrid photocatalyst for visible-light CO2 reduction
journal, January 2013
- Maeda, Kazuhiko; Sekizawa, Keita; Ishitani, Osamu
- Chemical Communications, Vol. 49, Issue 86
Introduction of a mediator for enhancing photocatalytic performance via post-synthetic metal exchange in metal–organic frameworks (MOFs)
journal, January 2015
- Sun, Dengrong; Liu, Wenjun; Qiu, Mei
- Chemical Communications, Vol. 51, Issue 11
Works referencing / citing this record:
Recent Innovation of Metal-Organic Frameworks for Carbon Dioxide Photocatalytic Reduction
journal, December 2019
- Kidanemariam, Alemayehu; Lee, Jiwon; Park, Juhyun
- Polymers, Vol. 11, Issue 12
Development of a new Lindqvist-like Fe6 cluster secondary building unit for MOFs
journal, January 2019
- Lin, Li-Dan; Li, Zhong; Zhao, Dan
- Chemical Communications, Vol. 55, Issue 72
A Tale of Two Trimers from Two Different Worlds: A COF‐Inspired Synthetic Strategy for Pore‐Space Partitioning of MOFs
journal, February 2019
- Wang, Yanxiang; Zhao, Xiang; Yang, Huajun
- Angewandte Chemie, Vol. 131, Issue 19
Highly open chalcogenide frameworks built from unusual defective supertetrahedral clusters
journal, January 2019
- Xue, Chaozhuang; Zhang, Li; Wang, Xiaoli
- Dalton Transactions, Vol. 48, Issue 29
Recent Advances in Photocatalysis over Metal–Organic Frameworks‐Based Materials
journal, December 2019
- Zhang, Yijun; Mao, Fangxin; Wang, Lijie
- Solar RRL, Vol. 4, Issue 5
Recent Progress on Exploring Stable Metal–Organic Frameworks for Photocatalytic Solar Fuel Production
journal, February 2020
- Wang, Xu‐Sheng; Li, Lan; Li, Dan
- Solar RRL, Vol. 4, Issue 8
A Tale of Two Trimers from Two Different Worlds: A COF-Inspired Synthetic Strategy for Pore-Space Partitioning of MOFs
journal, April 2019
- Wang, Yanxiang; Zhao, Xiang; Yang, Huajun
- Angewandte Chemie International Edition, Vol. 58, Issue 19
A Rigid Trigonal-Prismatic Hexagold Metallocage That Behaves as a Coronene Trap
journal, April 2019
- Ibáñez, Susana; Peris, Eduardo
- Angewandte Chemie International Edition, Vol. 58, Issue 20
Adjustment of the performance and stability of isostructural zeolitic tetrazolate-imidazolate frameworks
journal, January 2020
- Li, Hai-Zhen; Du, Dong-Ying; Sun, Yayong
- Dalton Transactions, Vol. 49, Issue 15
A Rigid Trigonal‐Prismatic Hexagold Metallocage That Behaves as a Coronene Trap
journal, April 2019
- Ibáñez, Susana; Peris, Eduardo
- Angewandte Chemie, Vol. 131, Issue 20
Recent Progress on Exploring Stable Metal–Organic Frameworks for Photocatalytic Solar Fuel Production
journal, August 2020
- Wang, Xu‐Sheng; Li, Lan; Li, Dan
- Solar RRL, Vol. 4, Issue 8