Ferrocenyl-Pyrenes, Ferrocenyl-9,10-Phenanthrenediones, and Ferrocenyl-9,10-Dimethoxyphenanthrenes: Charge-Transfer Studies and SWCNT Functionalization.,Chemistry - A European Journal

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Ferrocenyl-Pyrenes, Ferrocenyl-9,10-Phenanthrenediones, and Ferrocenyl-9,10-Dimethoxyphenanthrenes: Charge-Transfer Studies and SWCNT Functionalization.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-01-23 , DOI: 10.1002/chem.201904450
Andrea Preuß ₁ , Sebastian Notz ₁ , Eduard Kovalski ₁ , Marcus Korb _{1,

2} , Thomas Blaudeck _{3,

4} , Xiao Hu _{3,

4} , Jörg Schuster _{3,

4,

5} , Dominique Miesel ₁ , Tobias Rüffer ₁ , Alexander Hildebrandt ₁ , Katja Schreiter ₆ , Stefan Spange ₆ , Stefan E Schulz _{3,

4,

5} , Heinrich Lang _{1,

5}

Affiliation

The synthesis of 1-Fc- (3), 1-Br-6-Fc- (5 a), 2-Br-7-Fc- (7 a), 1,6-Fc2 - (5 b), 2,7-Fc2 -pyrene (7 b), 3,6-Fc2 -9,10-phenanthrenedione (10), and 3,6-Fc2 -9,10-dimethoxyphenanthrene (12; Fc=Fe(η5 -C5 H4 )(η5 -C5 H5 )) is discussed. Of these compounds, 10 and 12 form 1D or 2D coordination polymers in the solid state. (Spectro)Electrochemical studies confirmed reversible Fc/Fc+ redox events between -130 and 160 mV. 1,6- and 2,7-Substitution in 5 a (E°'=-130 mV) and 7 a (E°'=50 mV) influences the redox potentials, whereas the ones of 5 b and 7 b (E°'=20 mV) are independent. Compounds 5 b, 7 b, 10, and 12 show single Fc oxidation processes with redox splittings between 70 and 100 mV. UV/Vis/NIR spectroelectrochemistry confirmed a weak electron transfer between FeII /FeIII in mixed-valent [5 b]+ and [12]+ . DFT calculations showed that 5 b non-covalently interacts with the single-walled carbon nanotube (SWCNT) sidewalls as proven by, for example, disentangling experiments. In addition, CV studies of the as-obtained dispersions confirmed exohedral attachment of 5 b at the SWCNTs.

中文翻译：

二茂铁基-吡啶，二茂铁基-9,10-菲二烯和二茂铁基-9,10-二甲氧基菲：电荷转移研究和SWCNT功能化。

1-Fc-（3），1-Br-6-Fc-（5a），2-Br-7-Fc-（7a），1,6-Fc2-（5b），2的合成7-Fc2--（7 b），3,6-Fc2 -9,10-菲二酮（10）和3,6-Fc2 -9,10-二甲氧基菲（12; Fc = Fe（η5-C5H4）（讨论了η5 -C 5 H 5））。在这些化合物中，10和12形成固态的1D或2D配位聚合物。（光谱）电化学研究证实了-130至160 mV之间的可逆Fc / Fc +氧化还原事件。在5 a（E°'=-130 mV）和7 a（E°'= 50 mV）中进行1,6-和2,7取代会影响氧化还原电势，而5 b和7 b（E° '= 20 mV）是独立的。化合物5b，7b，10和12显示单个Fc氧化过程，氧化还原分裂在70和100 mV之间。UV / Vis / NIR光谱电化学证实了FeII / FeIII在混合价[5 b] +和[12] +中的弱电子转移。DFT计算表明，5b与单壁碳纳米管（SWCNT）侧壁发生非共价相互作用，例如通过解缠实验证明。另外，对所得分散体的CV研究证实了5b在SWCNT的面外附着。

更新日期：2020-01-23

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