Santoro, A, Lord, RM, Loughrey, JJ et al. (5 more authors) (2015) One-pot synthesis of highly emissive dipyridinium dihydrohelicenes. Chemistry - A European Journal, 21 (19). 7035 - 7038. ISSN 0947-6539
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 IC<inf>50</inf> values 12-30× that of cisplatin.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Santoro, A., Lord, R. M., Loughrey, J. J., McGowan, P. C., Halcrow, M. A., Henwood, A. F., Thomson, C. and Zysman-Colman, E. (2015), One-Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes. Chem. Eur. J., 21: 7035–7038. doi: 10.1002/chem.201406255, which has been published in final form at http://dx.doi.org/10.1002/chem.201406255. |
Keywords: | Crystal structures; Cytotoxicity; Fluorescence; Helical compounds; Voltammetry |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemistry (Leeds) > Inorganic Chemistry (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 27 Aug 2015 14:29 |
Last Modified: | 25 Mar 2016 00:53 |
Published Version: | http://dx.doi.org/10.1002/chem.201406255 |
Status: | Published |
Publisher: | Wiley-VCH Verlag |
Identification Number: | 10.1002/chem.201406255 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:84885 |