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首页> 外文期刊>Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics >Triferrocenes built on a C-3-symmetric ligand platform: Entry to redox-active pseudo-triphenylenes via chelation-driven stereoselection of triple Schiff bases
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Triferrocenes built on a C-3-symmetric ligand platform: Entry to redox-active pseudo-triphenylenes via chelation-driven stereoselection of triple Schiff bases

机译：在C-3-对称配体平台上构建的三茂铁：通过螯合驱动的三希夫碱立体选择进入氧化还原活性的伪三苯撑

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An expedient tandem deprotonation-trapping protocol was employed to prepare a tris(difluoroboronyl) complex of a triferrocenyl ligand that is geometrically analogous to substituted triphenylenes. A triple Schiff base condensation reaction between 1,3,5-triformylphloroglucinol and aminoferrocene afforded the tris(N-salicylideneamine) adducts 5a + 5b in ca. 1:1 ratio. The keto-enamine tautomeric core of this isomeric mixture could be converted to a common enolate-imine intermediate. Subsequent trapping with BF3 center dot Et2O cleanly afforded the tris(difluoroboronyl) adduct <6 in essentially quantitative yield. The electronic and structural properties of this new class of ferrocene compounds were investigated using various methods including UV-vis, cyclic voltammetry (CV), differential pulse voltammetry (DPV), and X-ray crystallography. In CH2Cl2-CH3CN, 6 displayed a reversible three-electron oxidation process at E-1/2(ox) = +210 mV (vs Fc/Fc(+)). Despite the sharing of a common [pi,pi]/[n,pi]-conjugated core, no significant electronic communication was observed among the three ferrocenyl units in 6 under either CV or DPV conditions. On the other hand, the broad oxidation wave of 5a + 5b at E-1/2(ox) = +60 mV in CH2Cl2-CH3CN was comprised of at least two major components at +20 and +90 mV, which collapsed to become a single peak in DMF electrolyte, despite that the ratios between the two isomers 5a,b remained essentially invariant to the change in solvent.
机译：一种方便的串联去质子捕获方案被用来制备三铁茂铁基配体的三（二氟硼基）络合物，其在几何学上类似于取代的三亚苯基。在1,3,5-三甲酰基间苯三酚和氨基二茂铁之间进行三重席夫碱缩合反应，得到大约三（N-水杨亚胺）加合物5a + 5b。 1：1比例。该异构体混合物的酮-烯胺互变异构体核心可转化为普通的烯醇盐-亚胺中间体。随后用BF 3中心点Et 2 O捕集，以基本上定量的收率干净地获得了<6的三（二氟硼基）加合物。使用各种方法，包括紫外可见光谱，循环伏安法（CV），微分脉冲伏安法（DPV）和X射线晶体学，研究了这类新型二茂铁化合物的电子和结构性质。在CH2Cl2-CH3CN中，6在E-1 / 2（ox）= +210 mV（vs Fc / Fc（+））处显示出可逆的三电子氧化过程。尽管共享共同的π，π/π，π共轭核，但是在CV或DPV条件下，在6中的三个二茂铁基单元之间未观察到明显的电子通信。另一方面，CH2Cl2-CH3CN中E-1 / 2（ox）= +60 mV时5a + 5b的宽氧化波由至少两个主要成分组成，分别在+20和+90 mV处折叠尽管两种异构体5a，b之间的比例对于溶剂的变化基本上保持不变，但DMF电解质中只有一个峰。

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