A Triply [5]Helicene‐Bridged (1,3,5)Cyclophane

2023/05/12 by Frédéric Aribot, A.M. Merle, Pierre Dechambenoit +7 · 1 voice
Chemistry · Materials Science · #Fullerene Chemistry and Applications #Photochromic and Fluorescence Chemistry #Synthesis and Properties of Aromatic Compounds

paper · pdf · doi:10.1002/anie.202304058

openalex publication_date 2023/05/12 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/22

Abstract

A rigid propeller-shaped conjugated triple macrocycle consisting of two nearly perfectly stacked benzene rings and three linking [5]helicene moieties has been synthesized using a glyoxylic Perkin approach. Analysis of the electron delocalization in this atypical aromatic molecule revealed global aromaticity and a 78 π-electron circuit along the edge of its triple loop, to the detriment of the two 6 π-electron circuits in the two stacked benzene rings.

Citations

• Chiroptical Properties of Symmetric Double, Triple, and Multiple Helicenes

Discussions

• sur l'ex que j'ai pris au hasard (pour illustrer le cas des images de chimie) il eût fallu que Wikipédia indique la source du papier dont est tirée cette TOC graphic: doi.org/10.1002/anie... [bsky, 1 points, 2 comments]

Related

• Synthesis and Structural Features of Quadruple Helicenes: Highly Distorted π Systems Enabled by Accumulation of Helical Repulsions
• Recent Development of Helicene Synthesis
• Effect of π‐Electron Conjugation on the Chiroptical Properties of Helicene Carbon Nanohoops
• Synthesis, Characterization, and Theory of [9]-, [12]-, and [18]Cycloparaphenylene: Carbon Nanohoop Structures
• Synthesis of Hexahelicene and 1-Methoxyhexahelicene via Cycloisomerization of Biphenylyl-Naphthalene Derivatives