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Research Article
Na Wang
Baotou Teachers’ College
Corresponding Author
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The spacer in diferrocenyl derivatives has significant effects on intramolecular electronic interaction properties. In this work, nine diferrocenyl five-membered heterocyclic molecules are synthesized as models to investigate the effect of intramolecular electron-transfer properties systematically, including 2,5-diferrocenyl-1-phenyl-pyrrole (1), 2,5-diferrocenylfuran (2), 2,5-diferrocenylthiophene (3), 2,5-diferrocenyl-1H-imidazole (4), 2,5-diferrocenyloxazole (5), 2,5-diferrocenylthiazole (6), 2,5-diferrocenyl-1,3,4-triazole (7), 2,5-diferrocenyl-1,3,4-oxadiazole (8) and 2,5-diferrocenyl-1,3,4-thiadiazole (9). The molecules were prepared in cyclization reaction and characterized by Elemental analysis, FT-IR, MS and NMR. Moreover, the molecular structures of 2,5-diferrocenylthiazole and 2,5-diferrocenyl-1,3,4-oxadiazole were determined by the single crystal X-ray diffraction. The intramolecular electronic interactions were investigated through cyclic voltammetry in combination with density functional theory (DFT) calculations. The results revealed that the electronic interaction decreased with the increase of heteroatoms in central heterocycle spacer, and the electron-transfer property could be regulated by regulate central heterocycle spacer species.
Keywords
diferrocenyl derivatives, intramolecular electronic interaction properties, central heterocycle spacer species
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No competing interests reported.
This is a list of supplementary files associated with this preprint. Click to download.
- SupportingInformation.docx
Additional information Crystallographic data for the structural analysis have been deposited at the Cambridge Crystallographic Data Centre, CCDC No. 1536574 and 1431129 for 6 and 8 respectively. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: t44-1223-336033; Email: [email protected]).
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This is a preprint, a preliminary version of a manuscript that has not completed peer review at a journal. Research Square does not conduct peer review prior to posting preprints. The posting of a preprint on this server should not be interpreted as an endorsement of its validity or suitability for dissemination as established information or for guiding clinical practice.
Research Article
Na Wang
Baotou Teachers’ College
Corresponding Author
Badges
Prescreen
This manuscript passed our Prescreen assessment
Complete author information
Appropriate declaration statements
Potential risks to human health
Prescreen
History
CURRENT STATUS: Posted
Version 1
Posted 08 Mar, 2021
No community comments so far
Metrics
Comments: 0
PDF Downloads: ...
HTML Views: ...
Subject Areas
Chemical Engineering
License:
This work is licensed under a CC BY 4.0 License. Read Full License
The spacer in diferrocenyl derivatives has significant effects on intramolecular electronic interaction properties. In this work, nine diferrocenyl five-membered heterocyclic molecules are synthesized as models to investigate the effect of intramolecular electron-transfer properties systematically, including 2,5-diferrocenyl-1-phenyl-pyrrole (1), 2,5-diferrocenylfuran (2), 2,5-diferrocenylthiophene (3), 2,5-diferrocenyl-1H-imidazole (4), 2,5-diferrocenyloxazole (5), 2,5-diferrocenylthiazole (6), 2,5-diferrocenyl-1,3,4-triazole (7), 2,5-diferrocenyl-1,3,4-oxadiazole (8) and 2,5-diferrocenyl-1,3,4-thiadiazole (9). The molecules were prepared in cyclization reaction and characterized by Elemental analysis, FT-IR, MS and NMR. Moreover, the molecular structures of 2,5-diferrocenylthiazole and 2,5-diferrocenyl-1,3,4-oxadiazole were determined by the single crystal X-ray diffraction. The intramolecular electronic interactions were investigated through cyclic voltammetry in combination with density functional theory (DFT) calculations. The results revealed that the electronic interaction decreased with the increase of heteroatoms in central heterocycle spacer, and the electron-transfer property could be regulated by regulate central heterocycle spacer species.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
No competing interests reported.
This is a list of supplementary files associated with this preprint. Click to download.
- SupportingInformation.docx
Additional information Crystallographic data for the structural analysis have been deposited at the Cambridge Crystallographic Data Centre, CCDC No. 1536574 and 1431129 for 6 and 8 respectively. Copies of this information may be obtained free of charge from the Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: t44-1223-336033; Email: [email protected]).
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