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| Language: | English |
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2024
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| Online Access: | https://doi.org/10.5281/zenodo.13497974 |
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| author | Nagler, Oliver Dubey, Rajeev K. Würthner, Frank |
| author_facet | Nagler, Oliver Dubey, Rajeev K. Würthner, Frank |
| contents | <p>Additional data to report <a title="DOI URL" href="https://doi.org/10.1021/acs.joc.4c02175">https://doi.org/10.1021/acs.joc.4c02175: </a></p> <p><span>Chiral organic molecules with a complementing π-structure are highly desired to obtain materials with good semiconducting properties and pronounced chirality effects in the visible region. Herein, we introduce a novel design strategy to achieve an axially chiral and rigid perylene bisimide (PBI) dye by attaching the chirality-inducing 2,2′-biphenoxy moiety at one side of the bay area and the rigidity-inducing di-</span><em>tert</em><span>-butylsilanediol bridge on the other side. This yielded a new bay-functionalized PBI derivative carrying the combination of a highly rigid and, simultaneously, an axially chiral perylene core. As a result, the derivative exhibits well-resolved absorption and emission spectra in the visible region, with a fluorescence quantum yield close to unity. Furthermore, the </span><em>M</em><span>- and </span><em>P</em><span>-enantiomers were found to be stable with a racemization barrier of 102 kJ mol</span><sup>–1</sup><span> and, hence, could be successfully separated by chiral chromatography and studied by circular dichroism (CD) spectroscopy. This rigidified chiral-PBI could also be crystallized and analyzed by X-ray diffraction, showing the highest torsion angle of the perylene core with a value of up to 30.3° in the family of PBIs carrying the same di-</span><em>tert</em><span>-butylsilanediol bridge.</span></p> |
| format | Recurso digital |
| id | zenodo_https___doi_org_10_5281_zenodo_13497974 |
| institution | Zenodo |
| language | eng |
| publishDate | 2024 |
| publisher | Zenodo |
| record_format | zenodo |
| spellingShingle | Silanediol-Bay-Bridge Rigidified Axially Chiral Perylene Bisimide Nagler, Oliver Dubey, Rajeev K. Würthner, Frank Chirality Perylene dyes Perylene bisimides Fluorescence <p>Additional data to report <a title="DOI URL" href="https://doi.org/10.1021/acs.joc.4c02175">https://doi.org/10.1021/acs.joc.4c02175: </a></p> <p><span>Chiral organic molecules with a complementing π-structure are highly desired to obtain materials with good semiconducting properties and pronounced chirality effects in the visible region. Herein, we introduce a novel design strategy to achieve an axially chiral and rigid perylene bisimide (PBI) dye by attaching the chirality-inducing 2,2′-biphenoxy moiety at one side of the bay area and the rigidity-inducing di-</span><em>tert</em><span>-butylsilanediol bridge on the other side. This yielded a new bay-functionalized PBI derivative carrying the combination of a highly rigid and, simultaneously, an axially chiral perylene core. As a result, the derivative exhibits well-resolved absorption and emission spectra in the visible region, with a fluorescence quantum yield close to unity. Furthermore, the </span><em>M</em><span>- and </span><em>P</em><span>-enantiomers were found to be stable with a racemization barrier of 102 kJ mol</span><sup>–1</sup><span> and, hence, could be successfully separated by chiral chromatography and studied by circular dichroism (CD) spectroscopy. This rigidified chiral-PBI could also be crystallized and analyzed by X-ray diffraction, showing the highest torsion angle of the perylene core with a value of up to 30.3° in the family of PBIs carrying the same di-</span><em>tert</em><span>-butylsilanediol bridge.</span></p> |
| title | Silanediol-Bay-Bridge Rigidified Axially Chiral Perylene Bisimide |
| topic | Chirality Perylene dyes Perylene bisimides Fluorescence |
| url | https://doi.org/10.5281/zenodo.13497974 |