One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

Santoro, Amedeo, Lord, Rianne M., Loughrey, Jonathan J., McGowan, Patrick C., Halcrow, Malcolm A., Henwood, Adam F., Thomson, Connor and Zysman-Colman, Eli (2015) One-pot synthesis of highly emissive dipyridinium dihydrohelicenes. Chemistry - A European Journal, 21 (19). pp. 7035-7038. ISSN 0947-6539

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 30 Jan 2020 04:15
Last Modified: 30 Jan 2020 04:15
URI: https://ueaeprints.uea.ac.uk/id/eprint/73878
DOI: 10.1002/chem.201406255

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