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    One-Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes

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    Santoro_ChemEurJ_2015.pdf (847.4Kb)
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    Publication date
    2015-05
    Author
    Santoro, A.
    Lord, Rianne M.
    Loughrey, J.J.
    McGowan, P.C.
    Halcrow, M.A.
    Henwood, A.F.
    Thomson, C.
    Zysman-Colman, E.
    Keyword
    Helical poly-aromatic compounds (helicenes); Dipyridinium Dihydrohelicenes; Anticancer agents; Cytotoxicity
    Peer-Reviewed
    yes
    
    Metadata
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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 28–458. 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 l=460– 600 nm. Preliminary cytotoxicity studies against HT-29 cancer cells demonstrated moderate-to-good activity, with IC50 values 12–30x that of cisplatin.
    URI
    http://hdl.handle.net/10454/9497
    Version
    Accepted manuscript
    Citation
    Santoro A, Lord RM, Loughrey JJ, McGowan PC, Halcrow MA, Henwood AF, Thomson C and Zysmann-Colman E (2015) One-Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes. Chemistry: A European Journal. 21 (19): 7035–7038.
    Link to publisher’s version
    http://dx.doi.org/10.1002/chem.201406255
    Type
    Article
    Collections
    Life Sciences Publications

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