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Nano Research 2022, 15(2): 1691-1697 https://doi.org/10.1007/s12274-021-3871-4
Research Article | Issue | Published: 11 October 2021

The effect of multiple pairs of meta-dicarboxyl groups on molecular self-assembly and the selective adsorption of coronene by hydrogen bonding and van der Waals forces

Show Author's Information Jianqiao Li1,2,3,  Wendi Luo1,  Siqi Zhang1,2,  Chunyu Ma1,2,  Xunwen Xiao3( ),  Wubiao Duan2( ),  Qingdao Zeng1( )
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China
Department of Chemistry, School of Science, Beijing Jiaotong University, Beijing 100044, China
School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo 315211, China
Keywords:
self-assembly, selective adsorption, steric hindrance, meta-dicarboxyl groups, hexagonal cavity
Topics:
Surface structure
Cite this article:
Li J, Luo W, Zhang S, et al. The effect of multiple pairs of meta-dicarboxyl groups on molecular self-assembly and the selective adsorption of coronene by hydrogen bonding and van der Waals forces. Nano Research, 2022, 15(2): 1691-1697. https://doi.org/10.1007/s12274-021-3871-4
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Abstract Full text Electronic supplementary material About this article

The prediction of two-dimensional molecular self-assembly structures has always been a problem to be solved. The molecules with meta-dicarboxyl groups can self-assemble into a specific hexagonal cavity, which has an important influence on the prediction of molecular self-assembly structures and the application of functional molecules with meta-dicarboxyl groups. Two kinds of molecules with four pairs of meta-dicarboxyl groups, 1,3,6,8-tetrakis(3,5-isophthalic acid)pyrene (H8TIAPy) and 4',4''',4''''',4'''''''-(ethene-1,1,2,2-tetrayl)tetrakis(([1,1’-biphenyl]-3,5-dicarboxylic acid)) (H8ETTB) molecules were chosen to observe the self-assembly behavior at the heptanoic acid/highly oriented pyrolytic graphite (HA/HOPG) interface. H8TIAPy molecules self-assembled into well-ordered quadrilateral structures and could be regulated into kagomé networks with hexagonal pores by coronene (COR) molecules. H8ETTB molecules self-assembled into lamellar structures and transformed into acid-COR-acid-COR co-assembled structures at low concentration of COR solution and acid-COR dimer-acid-COR dimer co-assembled structures at high concentration of COR solution. The reason that H8ETTB molecules could not be regulated into hexagonal porous architecture was attributed to the steric hindrance by the similar length and width of H8ETTB molecules. The H8ETTB templates had stronger adsorption for COR than that of hexaphenylbenzene (HPB), regardless of the order of molecular introduction.


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Electronic supplementary material
About this article

The effect of multiple pairs of meta-dicarboxyl groups on molecular self-assembly and the selective adsorption of coronene by hydrogen bonding and van der Waals forces

Show Author's information Jianqiao Li1,2,3, Wendi Luo1, Siqi Zhang1,2, Chunyu Ma1,2, Xunwen Xiao3( ), Wubiao Duan2( ), Qingdao Zeng1( )
CAS Key Laboratory of Standardization and Measurement for Nanotechnology, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology (NCNST), Beijing 100190, China
Department of Chemistry, School of Science, Beijing Jiaotong University, Beijing 100044, China
School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo 315211, China

Abstract

The prediction of two-dimensional molecular self-assembly structures has always been a problem to be solved. The molecules with meta-dicarboxyl groups can self-assemble into a specific hexagonal cavity, which has an important influence on the prediction of molecular self-assembly structures and the application of functional molecules with meta-dicarboxyl groups. Two kinds of molecules with four pairs of meta-dicarboxyl groups, 1,3,6,8-tetrakis(3,5-isophthalic acid)pyrene (H8TIAPy) and 4',4''',4''''',4'''''''-(ethene-1,1,2,2-tetrayl)tetrakis(([1,1’-biphenyl]-3,5-dicarboxylic acid)) (H8ETTB) molecules were chosen to observe the self-assembly behavior at the heptanoic acid/highly oriented pyrolytic graphite (HA/HOPG) interface. H8TIAPy molecules self-assembled into well-ordered quadrilateral structures and could be regulated into kagomé networks with hexagonal pores by coronene (COR) molecules. H8ETTB molecules self-assembled into lamellar structures and transformed into acid-COR-acid-COR co-assembled structures at low concentration of COR solution and acid-COR dimer-acid-COR dimer co-assembled structures at high concentration of COR solution. The reason that H8ETTB molecules could not be regulated into hexagonal porous architecture was attributed to the steric hindrance by the similar length and width of H8ETTB molecules. The H8ETTB templates had stronger adsorption for COR than that of hexaphenylbenzene (HPB), regardless of the order of molecular introduction.

Keywords: self-assembly, selective adsorption, steric hindrance, meta-dicarboxyl groups, hexagonal cavity

References(36)

1

Feng, Z. J.; Kladnik, G.; Comelli, G.; Dri, C.; Cossaro, A. growth of regular nanometric molecular arrays on a functional 2D template based on a chemical guest–host approach. Nanoscale 2018, 10, 2067–2072.
DOI Google Scholar
2

Silly, F. Concentration-dependent two-dimensional halogen-bonded self-assembly of 1,3,5-tris(4-iodophenyl)benzene molecules at the solid–liquid interface. J. Phys. Chem. C 2017, 121, 10413–10418.
DOI Google Scholar
3

Silly, F. Elucidating the intramolecular contrast in the STM images of 2,4,6-tris(4’,4’’,4’’’-trimethylphenyl)-1,3,5-triazine molecules recorded at room-temperature and at the liquid–solid interface. RSC Adv. 2020, 10, 5742–5746.
DOI Google Scholar
4

He, J.; Fang, C.; Shelp, R. A.; Zimmt, M. B. Tracking invisible transformations of physisorbed monolayers: LDI-TOF and MALDI-TOF mass spectrometry as complements to STM imaging. Langmuir 2017, 33, 459–467.
DOI Google Scholar
5

Wang, Y.; Tan, X. P.; Pang, P.; Li, B.; Miao, X. R.; Cheng, X. H.; Deng, W. L. Template-assisted 2D self-assembled chiral kagome network for selective adsorption of coronene. Chem. Commun. 2020, 56, 13991–13994.
DOI Google Scholar
6

Dai, H. L.; Yi, W. J.; Deng, K.; Wang, H.; Zeng, Q. D. Formation of coronene clusters in concentration and temperature controlled two-dimensional porous network. ACS Appl. Mater. Interfaces 2016, 8, 21095–21100.
DOI Google Scholar
7

Xiao, Y. C.; Tao, J. Y.; Peng, X.; Song, Y. T.; Lei, P.; Xu, H. J.; Xiao, X. W.; Tu, B.; Zeng, Q. D. Two-dimensional molecular network built from hierarchy self-assembly of perylene bisimide derivatives. ACS Appl. Mater. Interfaces 2021, 13, 17129–17138.
DOI Google Scholar
8

Guo, C.; Xue, J. D.; Cheng, L. X.; Liu, R. C.; Kang, S. Z.; Zeng, Q. D.; Li, M. Two-dimensional self-assembly of diacetylenic acid derivatives and their light-induced polymerization on HOPG surfaces. Phys. Chem. Chem. Phys. 2017, 19, 16213–16218.
DOI Google Scholar
9

Kikkawa, Y.; Tsuzuki, S.; Kashiwada, A.; Hiratani, K. Self-assembled 2D patterns of structural isomers in isobutenyl compounds revealed by STM at solid/liquid interface. Colloids Surf A: Physicochem. Eng. Aspects 2018, 537, 580–590.
DOI Google Scholar
10

Kim, S.; Castillo, H. D.; Lee, M.; Mortensen, R. D.; Tait, S. L.; Lee, D. From foldable open chains to shape-persistent macrocycles: Synthesis, impact on 2D ordering, and stimulated self-assembly. J. Am. Chem. Soc. 2018, 140, 4726–4735.
DOI Google Scholar
11

Reynaerts, R.; Minoia, A.; Gali, S. M.; Daukiya, L.; Van Velthoven, N.; De Vos, D.; Lazzaroni, R.; Mali, K. S.; De Feyter, S. Coplanar versus noncoplanar carboxyl groups: The influence of sterically enforced noncoplanarity on the 2D mixing behavior of benzene tricarboxylic acids. J. Phys. Chem. C 2020, 124, 24874–24882.
DOI Google Scholar
12

Martsinovich, N.; Troisi, A. Modeling the self-assembly of benzenedicarboxylic acids using Monte Carlo and molecular dynamics simulations. J. Phys. Chem. C 2010, 114, 4376–4388.
DOI Google Scholar
13

Peng, X.; Xiao, Y. C.; Mu, M.; Deng, K.; Tian, W.; Xiao, X. W.; Li, X. K.; Zeng, Q. D. Programmable binary crystallization behaviors assisted by hydrogen bond on HOPG surface. Appl. Surf. Sci. 2021, 565, 150529.
DOI Google Scholar
14

Li, J. Q.; Liu, B.; Duan, W. B.; Tu, B.; Zeng, Q. D. The Self-Assembly of a low symmetric aromatic carboxylic acid with meta-carboxyl groups regulated by pyridine derivatives. Surf. Sci. 2020, 700, 121654.
DOI Google Scholar
15

Mazur, U.; Hipps, K. W. Kinetic and thermodynamic processes of organic species at the solution-solid interface: The view through an STM. Chem. Commun. 2015, 51, 4737–4749.
DOI Google Scholar
16

Mairena, A.; Parschau, M.; Seibel, J.; Wienke, M.; Rentsch, D.; Terfort, A.; Ernst, K. H. Diastereoselective self-assembly of bisheptahelicene on Cu(111). Chem. Commun. 2018, 54, 8757–8760.
DOI Google Scholar
17

Hu, Y.; Miao, K.; Zha, B.; Xu, L.; Miao, X. R.; Deng, W. L. STM investigation of structural isomers: Alkyl chain position induced self-assembly at the liquid/solid interface. Phys. Chem. Chem. Phys. 2016, 18, 624–634.
DOI Google Scholar
18

Ciesielski, A.; Szabelski, P. J.; Rżysko, W.; Cadeddu, A.; Cook, T. R.; Stang, P. J.; Samorì, P. Concentration-dependent supramolecular engineering of hydrogen-bonded nanostructures at surfaces: Predicting self-assembly in 2D. J. Am. Chem. Soc. 2013, 135, 6942–6950.
DOI Google Scholar
19

Garah, M. E.; Dianat, A.; Cadeddu, A.; Gutierrez, R.; Cecchini, M.; Cook, T. R.; Ciesielski, A.; Stang, P. J.; Cuniberti, G.; Samori P. Atomically precise prediction of 2D self-assembly of weakly bonded nanostructures: STM insight into concentration-dependent architectures. Small 2016, 12, 343–350.
DOI Google Scholar
20

He, Y. B.; Zhou, W.; Krishna, R.; Chen, B. L. Microporous metal–organic frameworks for storage and separation of small hydrocarbons. Chem. Commun. 2012, 48, 11813–11831.
DOI Google Scholar
21

Li, B. Y.; Zhang, Z. J.; Li, Y.; Yao, K. X.; Zhu, Y. H.; Deng, Z. Y.; Yang, F.; Zhou, X. J.; Li, G. H.; Wu, H. H. et al. Enhanced binding affinity, remarkable selectivity, and high capacity of CO2 by dual functionalization of a rht-type metal–organic framework. Angew. Chem., Int. Ed. 2012, 51, 1412–1415.
DOI Google Scholar
22

Lin, R. B.; Xiang, S. C.; Li, B.; Cui, Y. J.; Zhou, W.; Qian, G. D.; Chen, B. L. Reticular chemistry of multifunctional metal–organic framework materials. Isr. J. Chem. 2018, 58, 949–961.
DOI Google Scholar
23

MacLeod, J. M.; Chaouch, Z. B.; Perepichka, D. F.; Rosei, F. Two-dimensional self-assembly of a symmetry-reduced tricarboxylic acid. Langmuir 2013, 29, 7318–7324.
DOI Google Scholar
24

Steeno, R.; Minoia, A.; Gimenez-Lopez, M. C.; Blunt, M. O.; Champness, N. R.; Lazzaroni, R.; Mali, K. S.; De Feyter, S. Molecular dopant determines the structure of a physisorbed self-assembled molecular network. Chem. Commun. 2021, 57, 1454–1457.
DOI Google Scholar
25

Li, M.; Deng, K.; Lei, S. B.; Yang, Y. L.; Wang, T. S.; Shen, Y. T.; Wang, C. R.; Zeng, Q. D.; Wang, C. Site-selective fabrication of two-dimensional fullerene arrays by using a supramolecular template at the liquid–solid interface. Angew. Chem., Int. Ed. 2008, 47, 6717–6721.
DOI Google Scholar
26

Shen, Y. T.; Li, M.; Guo, Y. Y.; Deng, K.; Zeng, Q. D.; Wang, C. The site-selective molecular recognition of ternary architectures by using supramolecular nanoporous networks at a liquid–solid interface. Chem. Asian J. 2010, 5, 787–790.
DOI Google Scholar
27

Blunt, M.; Lin, X.; Gimenez-Lopez, M. D. C.; Schröder, M.; Champness, N. R.; Beton, P. H. Directing two-dimensional molecular crystallization using guest templates. Chem. Commun. 2008, 2304–2306.
DOI Google Scholar
28

Wang, J.; Wang, L. M.; Lu, C.; Yan, H. J.; Wang, S. X.; Wang, D. Formation of multicomponent 2D assemblies of C2v-symmetric terphenyl tetracarboxylic acid at the solid/liquid interface: Recognition, selection, and transformation. RSC Adv. 2019, 9, 11659–11663.
DOI Google Scholar
29

Lackinger, M.; Griessl, S.; Heckl, W. M.; Hietschold, M.; Flynn, G. W. Self-assembly of trimesic acid at the liquid–solid interface—A study of solvent-induced polymorphism. Langmuir 2005, 21, 4984–4988.
DOI Google Scholar
30

Li, J. Q.; Tu, B.; Li, X. K.; Ma, C. Y.; Chen, C.; Duan, W. B.; Xiao, X. W.; Zeng, Q. D. Self-assembled flower structures formed by C3-symmetric aromatic carboxylic acids with meta-carboxyl groups. Chem. Commun. 2019, 55, 11599–11602.
DOI Google Scholar
31

Zhao, N.; Sun, F. X.; Zhang, S. X.; He, H. M.; Liu, J.; Li, Q.; Zhu, G. S. Deprotonation-triggered stokes shift fluorescence of an unexpected basic-stable metal–organic framework. Inorg. Chem. 2015, 54, 65–68.
DOI Google Scholar
32

Guo, X. L.; Zhu, N. S.; Wang, S. P.; Li, G. H.; Bai, F. Q.; Li, Y.; Han, Y. H.; Zou, B.; Chen, X. B.; Shi, Z. et al. Stimuli-responsive luminescent properties of tetraphenylethene-based strontium and cobalt metal–organic frameworks. Angew. Chem., Int. Ed. 2020, 59, 19716–19721.
DOI Google Scholar
33

Peng, X.; Geng, Y. F.; Zhang, M.; Cheng, F. L.; Cheng, L. X.; Deng, K.; Zeng, Q. D. Guest selectivity in the supramolecular host networks fabricated by van der Waals force and hydrogen bond. Nano Res. 2019, 12, 537–542.
DOI Google Scholar
34

Delley, B. From molecules to solids with the DMol3 approach. J. Chem. Phys. 2000, 113, 7756–7764.
DOI Google Scholar
35

Perdew, J. P.; Wang, Y. Accurate and simple analytic representation of the electron-gas correlation energy. Phys. Rev. B 1992, 45, 13244–13249.
DOI Google Scholar
36

Chang, S. Q.; Liu, R. C.; Wang, L. C.; Li, M.; Deng, K.; Zheng, Q. Y.; Zeng, Q. D. Formation of ordered coronene clusters in template utilizing the structural transformation of hexaphenylbenzene derivative networks on graphite surface. ACS Nano 2016, 10, 342–348.
DOI Google Scholar
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Publication history
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Acknowledgements

Publication history

Received: 28 July 2021
Revised: 01 September 2021
Accepted: 03 September 2021
Published: 11 October 2021
Issue date: February 2022

Copyright

© Tsinghua University Press and Springer-Verlag GmbH Germany, part of Springer Nature 2021

Acknowledgements

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21773041, and 21972031), the Strategic Priority Research Program of Chinese Academy of Sciences (No. XDB36000000), the Natural Science Foundation of Zhejiang Province (No. Y20B020032) and China Scholarship Council (No. 202007090155).

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