One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

Amedeo Santoro, Rianne M. Lord, Jonathan J. Loughrey, Patrick C. McGowan, Malcolm A. Halcrow, Adam Francis Henwood, Connor Thomson, Eli Zysman-Colman

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)
2 Downloads (Pure)

Abstract

Condensation of a pyridyl-2-carbaldehyde derivative with 2-(bromoethyl)amine hydrobromide gave tetracyclic pyrido[1,2-a]pyrido[1',2':3,4]imidazo-[2,1-c]-6,7-dihydropyrazinium dications in excellent yields. Crystal structures and NOE data demonstrated the helical character of the dications, the dihedral angles between the two pyrido groups ranging from 28-45°. An intermediate in the synthesis was also characterized. A much brighter emission compared to literature helicenes has been found, with quantum yields as high as 60 % in the range of λ=460-600 nm. Preliminary cytotoxicity studies against HT-29 cancer cells demonstrated moderate-to-good activity, with IC50 values 12-30× that of cisplatin.

Original languageEnglish
Pages (from-to)7035-7038
JournalChemistry - A European Journal
Volume21
Issue number19
Early online date24 Mar 2015
DOIs
Publication statusPublished - 4 May 2015

Keywords

  • Crystal structures
  • Cytotoxicity
  • Fluorescence
  • Helical compounds
  • Voltammetry

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