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One-Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes
Santoro, A. Lord, Rianne M. Loughrey, J.J. McGowan, P.C. Halcrow, M.A. Henwood, A.F. Thomson, C. Zysman-Colman, E.
Santoro, A.
Lord, Rianne M.
Loughrey, J.J.
McGowan, P.C.
Halcrow, M.A.
Henwood, A.F.
Thomson, C.
Zysman-Colman, E.
Publication Date
2015-05
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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.
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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.
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