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One-pot synthesis of highly emissive dipyridinium dihydrohelicenes
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dc.contributor.author | Santoro, Amedeo | |
dc.contributor.author | Lord, Rianne M. | |
dc.contributor.author | Loughrey, Jonathan J. | |
dc.contributor.author | McGowan, Patrick C. | |
dc.contributor.author | Halcrow, Malcolm A. | |
dc.contributor.author | Henwood, Adam Francis | |
dc.contributor.author | Thomson, Connor | |
dc.contributor.author | Zysman-Colman, Eli | |
dc.date.accessioned | 2016-03-24T00:01:15Z | |
dc.date.available | 2016-03-24T00:01:15Z | |
dc.date.issued | 2015-05-04 | |
dc.identifier.citation | 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 . https://doi.org/10.1002/chem.201406255 | en |
dc.identifier.issn | 0947-6539 | |
dc.identifier.other | PURE: 173137972 | |
dc.identifier.other | PURE UUID: 224e3514-af40-4268-879a-501f57db1900 | |
dc.identifier.other | Scopus: 84928383892 | |
dc.identifier.other | ORCID: /0000-0001-7183-6022/work/56639143 | |
dc.identifier.other | WOS: 000353348100009 | |
dc.identifier.uri | https://hdl.handle.net/10023/8478 | |
dc.description | This 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.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 28-45°. 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.language.iso | eng | |
dc.relation.ispartof | Chemistry - A European Journal | en |
dc.rights | © 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 | en |
dc.subject | Crystal structures | en |
dc.subject | Cytotoxicity | en |
dc.subject | Fluorescence | en |
dc.subject | Helical compounds | en |
dc.subject | Voltammetry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | SDG 3 - Good Health and Well-being | en |
dc.subject.lcc | QD | en |
dc.title | One-pot synthesis of highly emissive dipyridinium dihydrohelicenes | en |
dc.type | Journal article | en |
dc.description.version | Postprint | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1002/chem.201406255 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2016-03-24 | |
dc.identifier.url | http://onlinelibrary.wiley.com/doi/10.1002/chem.201406255/suppinfo | en |
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