A Near-Infrared Absorbing and Emissive Quadruple Helicene Enabled by the Scholl Reaction of Perylene

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

  • Sai Ho Pun
  • Ka Man Cheung
  • Daiyue Yang
  • Han Chen
  • Yujing Wang
  • And 2 others
  • Stephen V. Kershaw
  • Qian Miao

Detail(s)

Original languageEnglish
Article numbere202113203
Journal / PublicationAngewandte Chemie - International Edition
Volume61
Issue number8
Online published17 Dec 2021
Publication statusPublished - 14 Feb 2022

Abstract

Herein, we report the synthesis, structural analysis, optical and chiroptical properties of a novel quadruple helicene, which has two [6] and two [7]helicene moieties fused in a contorted framework of 92 sp2 carbon atoms. It was synthesized by the Scholl reaction of a perylene-containing substrate with the formation of eight carbon-carbon bonds on the perylene unit in a single synthetic operation. Chemical oxidation of the quadruple helicene with tris(4-bromophenyl)ammoniumyl hexachloroantimonate resulted in an air-stable dication, which exhibits the same helicity in its four helicene moieties as unambiguously identified by single-crystal X-ray crystallography. The quadruple helicene exhibits unusual near-infrared absorption and emission with absorption and emission maxima at 848 nm and 977 nm, respectively, and its isolated enantiomers exhibit electronic circular dichroism in the near-infrared and visible-light regions.

Research Area(s)

  • Chiroptical Properties, Helicenes, Near Infrared, Polycyclic Aromatics, Scholl Reactions

Citation Format(s)

A Near-Infrared Absorbing and Emissive Quadruple Helicene Enabled by the Scholl Reaction of Perylene. / Pun, Sai Ho; Cheung, Ka Man; Yang, Daiyue et al.

In: Angewandte Chemie - International Edition, Vol. 61, No. 8, e202113203, 14.02.2022.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review