Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers
The ability to engineer sophisticated two-dimensional tessellation organic nanoarchitectures based on triangular molecules and on-surface-synthesized covalent multimers is investigated using scanning tunneling microscopy. 1,3,5-Tris(3,5-dibromophenyl)benzene molecules are deposited on high-temperatu...
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MDPI AG
2023-07-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/14/11291 |
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| author | David Peyrot Fabien Silly |
| author_facet | David Peyrot Fabien Silly |
| author_sort | David Peyrot |
| collection | DOAJ |
| description | The ability to engineer sophisticated two-dimensional tessellation organic nanoarchitectures based on triangular molecules and on-surface-synthesized covalent multimers is investigated using scanning tunneling microscopy. 1,3,5-Tris(3,5-dibromophenyl)benzene molecules are deposited on high-temperature Au(111) surfaces to trigger Ullmann coupling. The self-assembly into a semi-regular rhombitrihexagonal tiling superstructure not only depends on the synthesis of the required covalent building blocks but also depends on their ratio. The organic tessellation nanoarchitecture is achieved when the molecules are deposited on a Au(111) surface at 145 <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><msup><mspace width="0.166667em"></mspace><mo>°</mo></msup><mi mathvariant="normal">C</mi></mrow></semantics></math></inline-formula>. This halogen-bonded structure is composed of triangular domains of intact molecules separated by rectangular rows of covalent dimers. The nearly hexagonal vertices are composed of covalent multimers. The experimental observations reveal that the perfect semi-regular rhombitrihexagonal tiling cannot be engineered because it requires, in addition to the dimers and intact molecules, the synthesis of covalent hexagons. This building block is only observed above 165 <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><msup><mspace width="0.166667em"></mspace><mo>°</mo></msup><mi mathvariant="normal">C</mi></mrow></semantics></math></inline-formula> and does not coexist with the other required organic buildings blocks. |
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| last_indexed | 2024-03-11T01:01:31Z |
| publishDate | 2023-07-01 |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-4859a246ff2543c29f0136a6e0b8ecbf2023-11-18T19:37:04ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-07-0124141129110.3390/ijms241411291Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent MultimersDavid Peyrot0Fabien Silly1CEA, CNRS, SPEC, TITANS, Université Paris-Saclay, F-91191 Gif sur Yvette, FranceCEA, CNRS, SPEC, TITANS, Université Paris-Saclay, F-91191 Gif sur Yvette, FranceThe ability to engineer sophisticated two-dimensional tessellation organic nanoarchitectures based on triangular molecules and on-surface-synthesized covalent multimers is investigated using scanning tunneling microscopy. 1,3,5-Tris(3,5-dibromophenyl)benzene molecules are deposited on high-temperature Au(111) surfaces to trigger Ullmann coupling. The self-assembly into a semi-regular rhombitrihexagonal tiling superstructure not only depends on the synthesis of the required covalent building blocks but also depends on their ratio. The organic tessellation nanoarchitecture is achieved when the molecules are deposited on a Au(111) surface at 145 <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><msup><mspace width="0.166667em"></mspace><mo>°</mo></msup><mi mathvariant="normal">C</mi></mrow></semantics></math></inline-formula>. This halogen-bonded structure is composed of triangular domains of intact molecules separated by rectangular rows of covalent dimers. The nearly hexagonal vertices are composed of covalent multimers. The experimental observations reveal that the perfect semi-regular rhombitrihexagonal tiling cannot be engineered because it requires, in addition to the dimers and intact molecules, the synthesis of covalent hexagons. This building block is only observed above 165 <inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><msup><mspace width="0.166667em"></mspace><mo>°</mo></msup><mi mathvariant="normal">C</mi></mrow></semantics></math></inline-formula> and does not coexist with the other required organic buildings blocks.https://www.mdpi.com/1422-0067/24/14/11291moleculeself-assemblyon-surface synthesiscovalent Ullmann couplingtessaliontilings |
| spellingShingle | David Peyrot Fabien Silly Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers International Journal of Molecular Sciences molecule self-assembly on-surface synthesis covalent Ullmann coupling tessalion tilings |
| title | Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers |
| title_full | Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers |
| title_fullStr | Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers |
| title_full_unstemmed | Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers |
| title_short | Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent Multimers |
| title_sort | toward two dimensional tessellation through halogen bonding between molecules and on surface synthesized covalent multimers |
| topic | molecule self-assembly on-surface synthesis covalent Ullmann coupling tessalion tilings |
| url | https://www.mdpi.com/1422-0067/24/14/11291 |
| work_keys_str_mv | AT davidpeyrot towardtwodimensionaltessellationthroughhalogenbondingbetweenmoleculesandonsurfacesynthesizedcovalentmultimers AT fabiensilly towardtwodimensionaltessellationthroughhalogenbondingbetweenmoleculesandonsurfacesynthesizedcovalentmultimers |