ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Synthesis and Chiroptical Activity of π-Expanded Electron-Rich Heterohelicenes Based on the 1,4-Dihydropyrrolo[3,2-b]pyrrole Core.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Synthesis and Chiroptical Activity of π-Expanded Electron-Rich Heterohelicenes Based on the 1,4-Dihydropyrrolo[3,2-b]pyrrole Core.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications.Beilstein journal of organic chemistry · 2025Review
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7 authors.
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Abstract
Herein, we report the synthesis and chiroptical characteristics of the first (double) helicenes possessing the 1,4-dihydropyrrolo[3,2-b]pyrrole (DHPP) moiety as their central core. We have developed a three-step synthesis with 6π-electrocyclization accompanied by HBr elimination as its key step. We found that, whereas for smaller peripheral arms double 6π-electrocyclization occurs smoothly forming a double helicene, in the case of longer polycyclic aromatic hydrocarbons the reaction becomes less efficient and mono-helicenes are the only products. The electron density distribution analysis of LUMO explains the different regioselectivity of 6π-electrocyclization. The synthesized heterohelicenes are characterized by greenish-blue emission, distinct solvatofluorochromism and good fluorescence quantum yields (up to 42 %). Moreover, the chiroptical measurements reveal that unsymmetrical double heterohelicene exhibits excellent circularly polarized luminescence brightness (B
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