Diferrocenes Bridged by a Geminal Diethynylethene Scaffold with Varying Pendant Substituents: Electronic Interactions in Cross-Conjugated System
A series of geminal diethynylethene (gem-DEE) bridged diferrocenyl compounds with varying pendant substituents at the side chain, including xanthene, thioxanthene, dibenzo[a,d]cycloheptene, and fluorene, is reported with the aim of exploring electronic interactions in the cross-conjugated system. Th...
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| Published in: | Organometallics Vol. 36; no. 21; pp. 4278 - 4286 |
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| Main Authors: | , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Amer Chemical Soc
13.11.2017
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| ISSN: | 0276-7333, 1520-6041 |
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| Abstract | A series of geminal diethynylethene (gem-DEE) bridged diferrocenyl compounds with varying pendant substituents at the side chain, including xanthene, thioxanthene, dibenzo[a,d]cycloheptene, and fluorene, is reported with the aim of exploring electronic interactions in the cross-conjugated system. The compounds 9-[bis(ferrocenylethynyl)methylene]-9H-xanthene (1), 9-[bis(ferrocenylethynyl)methylene]-9H-thioxanthene (2), 5-[bis(ferrocenylethynyl)methylene]-5H-dibenzo[a,d]-cycloheptene (3), and 9-[bis(ferrocenylethynyl)methylene]-9H-fluorene (4) were synthesized and characterized by using spectroscopic methods and single-crystal X-ray diffraction analyses. Electrochemical measurements using the weakly coordinating electrolyte Na[B{C6H3(3,5-CF3)(2)}(4)] reveal the moderate electronic coupling between the ferrocenyl (Fc) termini. Hush analysis of the intervalence charge-transfer (IVCT) bands for the monocation species is suggestive of the weakly coupled Robin-Day class II mixed-valence compounds. DFT and TDDFT calculations suggest that the low-energy transitions of these compounds mainly involve a metal to ligand charge transfer (MLCT) transition from the iron center of ferrocenyl termini to the pendant substituent. |
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| AbstractList | A series of geminal diethynylethene (gem-DEE) bridged diferrocenyl compounds with varying pendant substituents at the side chain, including xanthene, thioxanthene, dibenzo[a,d]cycloheptene, and fluorene, is reported with the aim of exploring electronic interactions in the cross-conjugated system. The compounds 9-[bis(ferrocenylethynyl)methylene]-9H-xanthene (1), 9-[bis(ferrocenylethynyl)methylene]-9H-thioxanthene (2), 5-[bis(ferrocenylethynyl)methylene]-5H-dibenzo[a,d]-cycloheptene (3), and 9-[bis(ferrocenylethynyl)methylene]-9H-fluorene (4) were synthesized and characterized by using spectroscopic methods and single-crystal X-ray diffraction analyses. Electrochemical measurements using the weakly coordinating electrolyte Na[B{C6H3(3,5-CF3)(2)}(4)] reveal the moderate electronic coupling between the ferrocenyl (Fc) termini. Hush analysis of the intervalence charge-transfer (IVCT) bands for the monocation species is suggestive of the weakly coupled Robin-Day class II mixed-valence compounds. DFT and TDDFT calculations suggest that the low-energy transitions of these compounds mainly involve a metal to ligand charge transfer (MLCT) transition from the iron center of ferrocenyl termini to the pendant substituent. |
| Author | Zhang, Xu Lu, Hai-Ting Li, Hua-Min Pan, Ying-Le Cao, Ke-Ke Zhang, Meng-Li Fan, Yang Zou, Guo-Dong Ma, Pei-Lin |
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| Keywords | QUANTUM-INTERFERENCE DIRUTHENIUM COMPLEXES FERROCENE DELTA-E-1/2 VALUES RUTHENIUM COMPLEXES DELOCALIZATION MIXED-VALENCE CHEMISTRY CHARGE-TRANSFER SOLID-STATE EXPANDED RADIALENES |
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| Title | Diferrocenes Bridged by a Geminal Diethynylethene Scaffold with Varying Pendant Substituents: Electronic Interactions in Cross-Conjugated System |
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