Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes

Sven M. Elbert; Kevin Baumgärtner; Joshua A. Esteves; Laura Weber; Frank Rominger; Michael Mastalerz

doi:10.1055/s-0040-1721851

Organic Materials, Table of Contents

CC BY-NC-ND 4.0 · Organic Materials 2020; 02(04): 358-361
DOI: 10.1055/s-0040-1721851

Focus Issue: Curved Organic π-Systems

Short Communication

Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes

Sven M. Elbert

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

,

Kevin Baumgärtner

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

,

Joshua A. Esteves

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

,

Laura Weber

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

,

Frank Rominger

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

,

Michael Mastalerz

^aOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

› Author Affiliations

Abstract

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Abstract

Two bench-stable and readily accessible pyrene-based diaryne precursors based on triflate as well as TMS triflate motifs are introduced and compared in their [4+2]-Diels–Alder reactions with tetracyclone to give an oligophenyl-substituted dibenzo[e,l]pyrene in both cases. By single-crystal X-ray analysis, this twistacene showed helical chirality and an end-to-end contortion of 49.6° due to steric repulsion.

Key words

polycyclic aromatic hydrocarbons - twistacene - Diels–Alder reaction - pyrenes - arynes

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References

References and Notes

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