One-Pot Synthesis of Highly Emissive Dipyridinium Dihydrohelicenes
View/ Open
Santoro_ChemEurJ_2015.pdf (847.4Kb)
Download
Publication date
2015-05Author
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
YesOpen Access status
openAccess
Metadata
Show full item recordAbstract
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.Version
Accepted manuscriptCitation
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 Version of Record
https://doi.org/10.1002/chem.201406255Type
Articleae974a485f413a2113503eed53cd6c53
https://doi.org/10.1002/chem.201406255