Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism
Three shape-persistent naphthylene–phenylene–acetylene macrocycles of identical backbone structures and extraannular substitution patterns but different (empty, apolar, polar) nanopore fillings are self-assembled at the solid/liquid interface of highly oriented pyrolytic graphite and 1,2,4-trichloro...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.294 |
| _version_ | 1818621483151261696 |
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| author | Joscha Vollmeyer Friederike Eberhagen Sigurd Höger Stefan-S. Jester |
| author_facet | Joscha Vollmeyer Friederike Eberhagen Sigurd Höger Stefan-S. Jester |
| author_sort | Joscha Vollmeyer |
| collection | DOAJ |
| description | Three shape-persistent naphthylene–phenylene–acetylene macrocycles of identical backbone structures and extraannular substitution patterns but different (empty, apolar, polar) nanopore fillings are self-assembled at the solid/liquid interface of highly oriented pyrolytic graphite and 1,2,4-trichlorobenzene. Submolecularly resolved images of the resulting two-dimensional (2D) crystalline monolayer patterns are obtained by in situ scanning tunneling microscopy. A concentration-dependent conformational polymorphism is found, and open and more dense packing motifs are observed. For all three compounds alike lattice parameters are found, therefore the intermolecular macrocycle distances are mainly determined by their size and symmetry. This is an excellent example that the graphite acts as a template for the macrocycle organization independent from their specific interior. |
| first_indexed | 2024-12-16T18:09:59Z |
| format | Article |
| id | doaj.art-4007565800924e1aab3913a446274471 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T18:09:59Z |
| publishDate | 2014-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-4007565800924e1aab3913a4462744712022-12-21T22:21:49ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-11-011012774278210.3762/bjoc.10.2941860-5397-10-294Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphismJoscha Vollmeyer0Friederike Eberhagen1Sigurd Höger2Stefan-S. Jester3Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyKekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, GermanyThree shape-persistent naphthylene–phenylene–acetylene macrocycles of identical backbone structures and extraannular substitution patterns but different (empty, apolar, polar) nanopore fillings are self-assembled at the solid/liquid interface of highly oriented pyrolytic graphite and 1,2,4-trichlorobenzene. Submolecularly resolved images of the resulting two-dimensional (2D) crystalline monolayer patterns are obtained by in situ scanning tunneling microscopy. A concentration-dependent conformational polymorphism is found, and open and more dense packing motifs are observed. For all three compounds alike lattice parameters are found, therefore the intermolecular macrocycle distances are mainly determined by their size and symmetry. This is an excellent example that the graphite acts as a template for the macrocycle organization independent from their specific interior.https://doi.org/10.3762/bjoc.10.294conformational polymorphismself-assembled monolayersshape-persistent macrocyclessolid/liquid interfacesupramolecular surface patterningtemplate |
| spellingShingle | Joscha Vollmeyer Friederike Eberhagen Sigurd Höger Stefan-S. Jester Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism Beilstein Journal of Organic Chemistry conformational polymorphism self-assembled monolayers shape-persistent macrocycles solid/liquid interface supramolecular surface patterning template |
| title | Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism |
| title_full | Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism |
| title_fullStr | Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism |
| title_full_unstemmed | Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism |
| title_short | Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism |
| title_sort | self assembled monolayers of shape persistent macrocycles on graphite interior design and conformational polymorphism |
| topic | conformational polymorphism self-assembled monolayers shape-persistent macrocycles solid/liquid interface supramolecular surface patterning template |
| url | https://doi.org/10.3762/bjoc.10.294 |
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