C- and S-Shaped Perylene Diimide Heterohelicenes: Modular Synthesis and Spiral-Stair-Like π-Stacking,Organic Letters

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C- and S-Shaped Perylene Diimide Heterohelicenes: Modular Synthesis and Spiral-Stair-Like π-Stacking
Organic Letters ( IF 4.9 ) Pub Date : 2022-04-27 , DOI: 10.1021/acs.orglett.2c00928
Li Zhang ₁ , Shuqi Chen ₁ , Jianbao Jiang ₁ , Xue Dong ₁ , Yapeng Cai ₁ , Hui-Jun Zhang ₁ , Jianbin Lin ₁ , Yun-Bao Jiang ₁

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A number of C- and S-shaped perylene diimide (PDI) heterohelicenes with high dipole moments were synthesized from simple perylene tetrabutylester (PTE). Taking advantage of the weak coordination ability of the sterically crowded peri ester groups in PTE, efficient Rh(III)-catalyzed 2,8- and 2,11-bisiodinations of the perylene core were realized. The 2,8- and 2,11-diiodinated PTEs and PDIs represent key synthons for further ortho-π-extensions. In contrast to most helical π-skeletons that feature loose molecular packings, enantiomerically pure C-shaped PDI azahelicenes adopt unique spiral-stair-like π-stacking superstructures.

中文翻译：

C 型和 S 型苝二亚胺杂环烯：模块化合成和螺旋阶梯状 π 堆叠

由简单的苝四丁酯 (PTE) 合成了许多具有高偶极矩的C型和S型苝二酰亚胺 (PDI) 杂螺烯。利用PTE中空间拥挤的过酯基团的弱配位能力，实现了高效的Rh(III)催化苝核的2,8-和2,11-二碘化。2,8-和 2,11-二碘化 PTE 和 PDI 代表了进一步邻-π-扩展的关键合成子。与大多数具有松散分子堆积的螺旋 π 骨架相比，对映体纯C形 PDI 氮杂环烯采用独特的螺旋楼梯状 π 堆叠超结构。

更新日期：2022-04-27

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