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dc.contributor.authorSantoro, Amedeo
dc.contributor.authorLord, Rianne M.
dc.contributor.authorLoughrey, Jonathan J.
dc.contributor.authorMcGowan, Patrick C.
dc.contributor.authorHalcrow, Malcolm A.
dc.contributor.authorHenwood, Adam Francis
dc.contributor.authorThomson, Connor
dc.contributor.authorZysman-Colman, Eli
dc.date.accessioned2016-03-24T00:01:15Z
dc.date.available2016-03-24T00:01:15Z
dc.date.issued2015-05-04
dc.identifier173137972
dc.identifier224e3514-af40-4268-879a-501f57db1900
dc.identifier84928383892
dc.identifier000353348100009
dc.identifier.citationSantoro , 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 . https://doi.org/10.1002/chem.201406255en
dc.identifier.issn0947-6539
dc.identifier.otherORCID: /0000-0001-7183-6022/work/56639143
dc.identifier.urihttps://hdl.handle.net/10023/8478
dc.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.en
dc.description.abstractCondensation 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.
dc.format.extent557322
dc.language.isoeng
dc.relation.ispartofChemistry - A European Journalen
dc.subjectCrystal structuresen
dc.subjectCytotoxicityen
dc.subjectFluorescenceen
dc.subjectHelical compoundsen
dc.subjectVoltammetryen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subjectSDG 3 - Good Health and Well-beingen
dc.subject.lccQDen
dc.titleOne-pot synthesis of highly emissive dipyridinium dihydrohelicenesen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1002/chem.201406255
dc.description.statusPeer revieweden
dc.date.embargoedUntil2016-03-24
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201406255/suppinfoen


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