Anthracene-porphyrin nanoribbons
π-Conjugated nanoribbons attract interest because of their unusual electronic structures and charge-transport behavior. Here, we report the synthesis of a series of fully edge-fused porphyrin-anthracene oligomeric ribbons (dimer and trimer), together with a computational study of the corresponding i...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2023
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| _version_ | 1826311666751504384 |
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| author | Zhu, H Chen, Q Rončević, I Christensen, KE Anderson, HL |
| author_facet | Zhu, H Chen, Q Rončević, I Christensen, KE Anderson, HL |
| author_sort | Zhu, H |
| collection | OXFORD |
| description | π-Conjugated nanoribbons attract interest because of their unusual electronic structures and charge-transport behavior. Here, we report the synthesis of a series of fully edge-fused porphyrin-anthracene oligomeric ribbons (dimer and trimer), together with a computational study of the corresponding infinite polymer. The porphyrin dimer and trimer were synthesized in high yield, via oxidative cyclodehydrogenation of singly linked precursors, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoromethanesulfonic acid (TfOH). The crystal structure of the dimer shows that the central π-system is flat, with a slight S-shaped wave distortion at each porphyrin terminal. The extended π-conjugation causes a dramatic red-shift in the absorption spectra: the absorption maxima of the fused dimer and trimer appear at 1188 nm and 1642 nm, respectively (for the nickel complexes dissolved in toluene). The coordinated metal in the dimer was changed from Ni to Mg, using <i>p</i>-tolylmagnesium bromide, providing access to free-base and Zn complexes. These results open a versatile avenue to longer π-conjugated nanoribbons with integrated metalloporphyrin units. |
| first_indexed | 2024-03-07T08:14:37Z |
| format | Journal article |
| id | oxford-uuid:c3bef69f-74e0-4afb-a30b-bae7561c38b2 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T08:14:37Z |
| publishDate | 2023 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:c3bef69f-74e0-4afb-a30b-bae7561c38b22023-12-14T14:54:43ZAnthracene-porphyrin nanoribbonsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:c3bef69f-74e0-4afb-a30b-bae7561c38b2EnglishSymplectic ElementsWiley2023Zhu, HChen, QRončević, IChristensen, KEAnderson, HLπ-Conjugated nanoribbons attract interest because of their unusual electronic structures and charge-transport behavior. Here, we report the synthesis of a series of fully edge-fused porphyrin-anthracene oligomeric ribbons (dimer and trimer), together with a computational study of the corresponding infinite polymer. The porphyrin dimer and trimer were synthesized in high yield, via oxidative cyclodehydrogenation of singly linked precursors, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and trifluoromethanesulfonic acid (TfOH). The crystal structure of the dimer shows that the central π-system is flat, with a slight S-shaped wave distortion at each porphyrin terminal. The extended π-conjugation causes a dramatic red-shift in the absorption spectra: the absorption maxima of the fused dimer and trimer appear at 1188 nm and 1642 nm, respectively (for the nickel complexes dissolved in toluene). The coordinated metal in the dimer was changed from Ni to Mg, using <i>p</i>-tolylmagnesium bromide, providing access to free-base and Zn complexes. These results open a versatile avenue to longer π-conjugated nanoribbons with integrated metalloporphyrin units. |
| spellingShingle | Zhu, H Chen, Q Rončević, I Christensen, KE Anderson, HL Anthracene-porphyrin nanoribbons |
| title | Anthracene-porphyrin nanoribbons |
| title_full | Anthracene-porphyrin nanoribbons |
| title_fullStr | Anthracene-porphyrin nanoribbons |
| title_full_unstemmed | Anthracene-porphyrin nanoribbons |
| title_short | Anthracene-porphyrin nanoribbons |
| title_sort | anthracene porphyrin nanoribbons |
| work_keys_str_mv | AT zhuh anthraceneporphyrinnanoribbons AT chenq anthraceneporphyrinnanoribbons AT roncevici anthraceneporphyrinnanoribbons AT christensenke anthraceneporphyrinnanoribbons AT andersonhl anthraceneporphyrinnanoribbons |