One-pot synthesis of highly emissive dipyridinium dihydrohelicenes
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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.
Santoro , A , Lord , R M , Loughrey , J J , McGowan , P C , Halcrow , M A , Henwood , A F , Thomson , C & Zysman-Colman , E 2015 , ' One-pot synthesis of highly emissive dipyridinium dihydrohelicenes ' Chemistry - A European Journal , vol 21 , no. 19 , pp. 7035-7038 . DOI: 10.1002/chem.201406255
Chemistry - A European Journal
© 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., which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/chem.201406255/abstract
DescriptionThis work was funded by the EPSRC (EP/I014039/1). E.Z.C. acknowledges the University of St. Andrews for funding. C.T. thanks MUSA for financial support.
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