Pyrene-Based Diarynes as Precursors for Twisted Fused Polycyclic Aromatic Hydrocarbons: A Comparison of Two Routes-Reference-Cited by-同舟云学术

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

Published:2020-10 Issue:04 Volume:02 Page:358-361
ISSN:2625-1825
Container-title:Organic Materials
language:en
Short-container-title:Organic Materials

Author:

Elbert Sven M.¹,Baumgärtner Kevin¹,Esteves Joshua A.¹,Weber Laura¹,Rominger Frank¹,Mastalerz Michael¹

Affiliation:

1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

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.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Georg Thieme Verlag KG

Subject

Materials Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1721851.pdf

Reference12 articles.

1. Pyrene-Containing Twistarene: Twelve Benzene Rings Fused in a Row

2. Synthesis of Large Polycyclic Aromatic Hydrocarbons: Variation of Size and Periphery

3. Suppressing Aggregation in a Large Polycyclic Aromatic Hydrocarbon