One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

Amedeo Santoro; Rianne M. Lord; Jonathan J. Loughrey; Patrick C. McGowan; Malcolm A. Halcrow; Adam Francis Henwood; Connor Thomson; Eli Zysman-Colman

doi:10.1002/chem.201406255

One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

Amedeo Santoro, Rianne M. Lord, Jonathan J. Loughrey, Patrick C. McGowan, Malcolm A. Halcrow, Adam Francis Henwood, Connor Thomson, Eli Zysman-Colman

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	7035-7038
Journal	Chemistry - A European Journal
Volume	21
Issue number	19
Early online date	24 Mar 2015
DOIs	https://doi.org/10.1002/chem.201406255
Publication status	Published - 4 May 2015

Keywords

Crystal structures
Cytotoxicity
Fluorescence
Helical compounds
Voltammetry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/chem.201406255

Colman_2015_ChenEU_Helicenes_AM
© 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
Accepted author manuscript, 544 KB

Cite this

@article{224e3514af404268879a501f57db1900,

title = "One-pot synthesis of highly emissive dipyridinium dihydrohelicenes",

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.",

keywords = "Crystal structures, Cytotoxicity, Fluorescence, Helical compounds, Voltammetry",

author = "Amedeo Santoro and Lord, {Rianne M.} and Loughrey, {Jonathan J.} and McGowan, {Patrick C.} and Halcrow, {Malcolm A.} and Henwood, {Adam Francis} and Connor Thomson and Eli Zysman-Colman",

note = "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. ",

year = "2015",

month = may,

day = "4",

doi = "10.1002/chem.201406255",

language = "English",

volume = "21",

pages = "7035--7038",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "John Wiley & Sons, Ltd",

number = "19",

}

TY - JOUR

T1 - One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

AU - Santoro, Amedeo

AU - Lord, Rianne M.

AU - Loughrey, Jonathan J.

AU - McGowan, Patrick C.

AU - Halcrow, Malcolm A.

AU - Henwood, Adam Francis

AU - Thomson, Connor

AU - Zysman-Colman, Eli

N1 - 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.

PY - 2015/5/4

Y1 - 2015/5/4

N2 - 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.

AB - 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.

KW - Crystal structures

KW - Cytotoxicity

KW - Fluorescence

KW - Helical compounds

KW - Voltammetry

UR - http://onlinelibrary.wiley.com/doi/10.1002/chem.201406255/suppinfo

U2 - 10.1002/chem.201406255

DO - 10.1002/chem.201406255

M3 - Article

SN - 0947-6539

VL - 21

SP - 7035

EP - 7038

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 19

ER -

One-pot synthesis of highly emissive dipyridinium dihydrohelicenes

Abstract

Keywords

UN SDGs

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