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

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

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1721851.

Publication History

Received: 20 October 2020

Accepted: 12 November 2020

Article published online:
23 December 2020

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