N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation,Chemical Science

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N-doped nonalternant aromatic belt via a six-fold annulative double N-arylation
Chemical Science ( IF 7.6 ) Pub Date : 2022-08-09 , DOI: 10.1039/d2sc02647c
Hiroki Sato ₁ , Rie Suizu _{2,

3} , Tomoki Kato ₂ , Akiko Yagi ₁ , Yasutomo Segawa _{2,

4,

5,

6} , Kunio Awaga _{2,

7} , Kenichiro Itami _{1,

2,

6,

7}

Affiliation

The design and synthesis of nitrogen (N)-doped molecular nanocarbons are of importance since N-doped nanocarbons have received significant attention in materials science. Herein, we report the synthesis and X-ray crystal structure of a nitrogen-inserted nonalternant aromatic belt. The palladium-catalyzed six-fold annulative double N-arylation provided an aromatic belt bearing six nitrogen atoms in one step from cyclo[6]paraphenylene-Z-ethenylene, the precursor of the (6,6)carbon nanobelt. The C_3i-symmetric structure of the aromatic belt in the solid state was revealed using X-ray crystallography. The multistep (electro)chemical oxidation behavior of the belt, which was facilitated by the six p-methoxyaniline moieties, was studied, and a stable dication species was successfully identified by X-ray crystallography. The present study not only shows the unique structure and properties of the N-doped nonalternant aromatic belt but also expands the scope of accessibility of synthetically difficult belt molecules by the conventional intramolecular contraction pathway.

中文翻译：

通过六重环状双 N-芳基化的 N 掺杂非交替芳香带

氮 (N) 掺杂的分子纳米碳的设计和合成具有重要意义，因为 N 掺杂的纳米碳在材料科学中受到了极大的关注。在此，我们报告了插入氮的非交替芳香带的合成和 X 射线晶体结构。钯催化的六重环状双 N-芳基化从(6,6) 碳纳米带的前体环 [6] 对亚苯基-Z-亚乙基一步中提供了带有六个氮原子的芳族带。使用 X 射线晶体学揭示了固态芳烃带的C _{3i对称结构。}带的多步（电）化学氧化行为，这是由六个p促进的对-甲氧基苯胺部分进行了研究，并通过 X 射线晶体学成功鉴定了稳定的双阳离子物种。本研究不仅展示了 N 掺杂非交替芳香带的独特结构和性质，而且通过常规的分子内收缩途径扩大了合成困难带分子的可及性范围。

更新日期：2022-08-12

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