Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly
The position of the peripheral nitrogen atoms in bis(terpyridine)-derived oligopyridines (BTPs) has a strong impact on their self-assembly behavior at the liquid/HOPG (highly oriented pyrolytic graphite) interface. The intermolecular hydrogen bonding interactions in these peripheral pyridine units s...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2011-07-01
|
| Series: | Beilstein Journal of Nanotechnology |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjnano.2.46 |
| _version_ | 1818932931141304320 |
|---|---|
| author | Daniel Caterbow Daniela Künzel Michael G. Mavros Axel Groß Katharina Landfester Ulrich Ziener |
| author_facet | Daniel Caterbow Daniela Künzel Michael G. Mavros Axel Groß Katharina Landfester Ulrich Ziener |
| author_sort | Daniel Caterbow |
| collection | DOAJ |
| description | The position of the peripheral nitrogen atoms in bis(terpyridine)-derived oligopyridines (BTPs) has a strong impact on their self-assembly behavior at the liquid/HOPG (highly oriented pyrolytic graphite) interface. The intermolecular hydrogen bonding interactions in these peripheral pyridine units show specific 2D structures for each BTP isomer. From nine possible constitutional isomers only four have been described in the literature. The synthesis and self-assembling behavior of an additional isomer is presented here, but the remaining four members of the series are synthetically inaccessible. The self-assembling properties of three of the missing four BTP isomers can be mimicked by making use of the energetically preferred N–C–C–N transoid conformation between 2,2'-bipyridine subunits in a new class of so-called septipyridines. The structures are investigated by scanning tunneling microscopy (STM) and a combination of force-field and first-principles electronic structure calculations. |
| first_indexed | 2024-12-20T04:40:19Z |
| format | Article |
| id | doaj.art-05086fe729a14f8fa0f02be0150c1c32 |
| institution | Directory Open Access Journal |
| issn | 2190-4286 |
| language | English |
| last_indexed | 2024-12-20T04:40:19Z |
| publishDate | 2011-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Nanotechnology |
| spelling | doaj.art-05086fe729a14f8fa0f02be0150c1c322022-12-21T19:53:09ZengBeilstein-InstitutBeilstein Journal of Nanotechnology2190-42862011-07-012140541510.3762/bjnano.2.462190-4286-2-46Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assemblyDaniel Caterbow0Daniela Künzel1Michael G. Mavros2Axel Groß3Katharina Landfester4Ulrich Ziener5Institute of Organic Chemistry III/Macromolecular ChemistryInstitute of Theoretical Chemistry, University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, GermanyInstitute of Organic Chemistry III/Macromolecular ChemistryInstitute of Theoretical Chemistry, University of Ulm, Albert-Einstein-Allee 11, D-89081 Ulm, GermanyMax Planck Institute for Polymer Research, Ackermannweg 10, D-55128 Mainz, GermanyInstitute of Organic Chemistry III/Macromolecular ChemistryThe position of the peripheral nitrogen atoms in bis(terpyridine)-derived oligopyridines (BTPs) has a strong impact on their self-assembly behavior at the liquid/HOPG (highly oriented pyrolytic graphite) interface. The intermolecular hydrogen bonding interactions in these peripheral pyridine units show specific 2D structures for each BTP isomer. From nine possible constitutional isomers only four have been described in the literature. The synthesis and self-assembling behavior of an additional isomer is presented here, but the remaining four members of the series are synthetically inaccessible. The self-assembling properties of three of the missing four BTP isomers can be mimicked by making use of the energetically preferred N–C–C–N transoid conformation between 2,2'-bipyridine subunits in a new class of so-called septipyridines. The structures are investigated by scanning tunneling microscopy (STM) and a combination of force-field and first-principles electronic structure calculations.https://doi.org/10.3762/bjnano.2.46oligopyridinesself-assembled monolayerSTM |
| spellingShingle | Daniel Caterbow Daniela Künzel Michael G. Mavros Axel Groß Katharina Landfester Ulrich Ziener Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly Beilstein Journal of Nanotechnology oligopyridines self-assembled monolayer STM |
| title | Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly |
| title_full | Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly |
| title_fullStr | Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly |
| title_full_unstemmed | Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly |
| title_short | Septipyridines as conformationally controlled substitutes for inaccessible bis(terpyridine)-derived oligopyridines in two-dimensional self-assembly |
| title_sort | septipyridines as conformationally controlled substitutes for inaccessible bis terpyridine derived oligopyridines in two dimensional self assembly |
| topic | oligopyridines self-assembled monolayer STM |
| url | https://doi.org/10.3762/bjnano.2.46 |
| work_keys_str_mv | AT danielcaterbow septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly AT danielakunzel septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly AT michaelgmavros septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly AT axelgroß septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly AT katharinalandfester septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly AT ulrichziener septipyridinesasconformationallycontrolledsubstitutesforinaccessiblebisterpyridinederivedoligopyridinesintwodimensionalselfassembly |