Simon E. Lewis

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Organization: University of Bath , England

Department: Department of Chemistry

Title: (PhD)

TOPICS

Organic Chemistry

Dye Sensitized Solar Cell

Material Chemistry

Dye Sensitized Solar Cell

Chemicals
References

Azulene–boronate esters: colorimetric indicators for fluoride in drinking water

Co-reporter:Carlos M. López-Alled;Adrian Sanchez-Fernandez;Karen J. Edler;Adam C. Sedgwick;Steven D. Bull;Claire L. McMullin;Gabriele Kociok-Köhn;Tony D. James;Jannis Wenk

Chemical Communications 2017 vol. 53(Issue 93) pp:12580-12583

Publication Date(Web):2017/11/21

DOI:10.1039/C7CC07416F

Low cost and in situ fluoride detection by non-experts is important for the determination of drinking water safety in developing countries. Colour reagents can provide results quickly without expensive equipment, but colorimetric fluoride indicators are often nonspecific, complex to use or do not work in water. Here we show that azulene–boronate indicators respond selectively to fluoride at concentrations relevant to the WHO limit of 1.5 mg L−1.

What difference does a thiophene make? Evaluation of a 4,4′-bis(thiophene) functionalised 2,2′-bipyridyl copper(I) complex in a dye-sensitized solar cell

Co-reporter:Kathryn A. Wills, Humberto J. Mandujano-Ramírez, Gabriel Merino, Gerko Oskam, Paul Cowper, Matthew D. Jones, Petra J. Cameron, Simon E. Lewis

Dyes and Pigments 2016 Volume 134() pp:419-426

Publication Date(Web):November 2016

DOI:10.1016/j.dyepig.2016.07.023

•A new copper complex bearing thienyl-bipyridine ligands was prepared.•Dye-sensitized solar cells using this complex were constructed and evaluated.•Comparisons are made with an analogous dye which lacks the thiophene motifs.The synthesis of a 4,4′-bis(2-thienyl-5-carboxylic acid) functionalised 2,2′-bipyridine ligand and corresponding copper(I) complex is described and its application in a dye-sensitized solar cell (DSSC) is studied. The positioning of the thiophene groups appears favourable from DFT analysis and a best efficiency of 1.41% was obtained with this dye, for a 0.3 cm2 cell area DSSC. Two absorbance bands are observed in the electronic absorption spectrum of the copper(I) complex at 316 nm and 506 nm, with ε values of 50,000 M−1 cm−1 and 9030 M−1 cm−1, respectively. Cyclic voltammetry and electrochemical impedance spectroscopy are also used to provide a detailed analysis of the dye and assess its functionality in a DSSC.Figure optionsDownload full-size imageDownload as PowerPoint slide

C–H Functionalization of sp3 Centers with Aluminum: A Computational and Mechanistic Study of the Baddeley Reaction of Decalin

Co-reporter:Catherine L. Lyall ; Makoto Sato ; Mario Uosis-Martin ; Syeda Farina Asghar ; Matthew D. Jones ; Ian H. Williams

Journal of the American Chemical Society 2014 Volume 136(Issue 39) pp:13745-13753

Publication Date(Web):September 8, 2014

DOI:10.1021/ja5062246

Decalin undergoes reaction with aluminum trichloride and acetyl chloride to form a tricyclic enol ether in good yield, as first reported by Baddeley. This eye-catching transformation, which may be considered to be an aliphatic Friedel–Crafts reaction, has not previously been studied mechanistically. Here we report experimental and computational studies to elucidate the mechanism of this reaction. We give supporting evidence for the proposition that, in the absence of unsaturation, an acylium ion acts as a hydride acceptor, forming a tertiary carbocation. Loss of a proton introduces an alkene, which reacts with a further acylium ion. A concerted 1,2-hydride shift/oxonium formation, followed by elimination, leads to formation of the observed product.

Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Co-reporter:Catherine L. Lyall, Camilla C. Shotton, Monserrat Pérez-Salvia, G. Dan Pantoş and Simon E. Lewis

Chemical Communications 2014 vol. 50(Issue 89) pp:13837-13840

Publication Date(Web):18 Sep 2014

DOI:10.1039/C4CC06522K

We report the first boron-substituted naphthalenediimides (NDIs), prepared by iridium catalysed C–H activation. When the NDI substrates bear N-benzyl substituents, the naphthyl NDI core is borylated in preference, suggestive of a directed borylation mechanism. Borylated NDIs are substrates for Suzuki–Miyaura couplings and borylation of an NDI bearing two inequivalent N-substituents has also been demonstrated.

The enone motif of (+)-grandifloracin is not essential for ‘anti-austerity’ antiproliferative activity

Co-reporter:Monika Ali Khan, Pauline J. Wood, Natasha M. Lamb-Guhren, Lorenzo Caggiano, Gabriele Kociok-Köhn, David Tosh, Simon E. Lewis

Bioorganic & Medicinal Chemistry Letters 2014 Volume 24(Issue 13) pp:2815-2819

Publication Date(Web):1 July 2014

DOI:10.1016/j.bmcl.2014.04.111

We report the synthesis and biological evaluation of three analogues of the natural product (+)-grandifloracin (+)-1. All three analogues exhibit enhanced antiproliferative activity against PANC-1 and HT-29 cells compared to the natural product. The retention of activity in an analogue lacking the enone functional group, 9, implies this structural element is not an essential part of the (+)-grandifloracin pharmacophore.Figure optionsDownload full-size imageDownload as PowerPoint slide

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

Co-reporter:Catherine L. Lyall, Mario Uosis-Martin, John P. Lowe, Mary F. Mahon, G. Dan Pantoş and Simon E. Lewis

Organic & Biomolecular Chemistry 2013 vol. 11(Issue 9) pp:1468-1475

Publication Date(Web):21 Dec 2012

DOI:10.1039/C2OB26765A

The functionalisation of decalin by means of an “aliphatic Friedel–Crafts” reaction was reported over fifty years ago by Baddeley et al. This protocol is of current relevance in the context of C–H activation and here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation of the products is described and a mechanistic rationale for their formation is presented. The “aliphatic Friedel–Crafts” procedure allows for production of novel oxygenated building blocks from abundant hydrocarbons and as such can be considered to add significant synthetic value in a single step.

A Model System for the Synthesis of Complanadine Alkaloids by “Diverted Kondrat’eva” Oxazole–Olefin Cycloaddition

Co-reporter:Mario Uosis-Martin, G. Dan Pantoş, Mary F. Mahon, and Simon E. Lewis

The Journal of Organic Chemistry 2013 Volume 78(Issue 12) pp:6253-6263

Publication Date(Web):May 28, 2013

DOI:10.1021/jo401014n

A synthetic approach to complanadine alkaloids is described which employs a Kondrat’eva reaction to construct the pyridine rings. The viability of this approach is demonstrated by its application to a model substrate accessed from unfunctionalized decalin. The key transformation affords the desired tetracyclic architecture with unprecedented incorporation of substituents on the pyridine ring, implicating the oxazole α-hydroxy group as an active participant in the cycloadduct fragmentation process.

Photooxygenation of a Microbial Arene Oxidation Product and Regioselective KornblumDeLaMare Rearrangement: Total Synthesis of Zeylenols and Zeylenones

Co-reporter:Dr. Matthew J. Palframan;Dr. Gabriele Kociok-Köhn;Dr. Simon E. Lewis

Chemistry - A European Journal 2012 Volume 18( Issue 15) pp:4766-4774

Publication Date(Web):

DOI:10.1002/chem.201104035

Abstract

We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (−)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum–DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product.

Valuable New Cyclohexadiene Building Blocks from Cationic 5-IronCarbonyl Complexes Derived from a Microbial Arene Oxidation Product

Co-reporter:Monika AliKhan;Dr. Mary F. Mahon;Dr. John P. Lowe;Dr. Alan J. W. Stewart;Dr. Simon E. Lewis

Chemistry - A European Journal 2012 Volume 18( Issue 42) pp:13480-13493

Publication Date(Web):

DOI:10.1002/chem.201202411

Abstract

Biooxidation of benzoic acid by Ralstonia eutropha B9 provides an unusual cyclohexadiene carboxy diol that contains a quaternary stereocentre. Tricarbonyliron derivatives of this chiron, on treatment with acid, give two isomeric η⁵-cyclohexadienyl complexes as observed by NMR spectroscopy. Both of these can be subjected to the addition of nucleophiles to provide isomeric cyclohexadiene complexes with new substituent patterns, several of which have been characterised crystallographically. De-metallation of these provides a versatile library of cyclohexadiene building blocks, the utility of which is demonstrated by formal syntheses of oseltamivir. The mechanism of product formation and its stereochemical implications are discussed, as are the procedures undertaken to establish the enantiopurity of a representative cyclohexadiene product.

Accessing the antipodal series in microbial arene oxidation: a novel diene rearrangement induced by tricarbonyliron(0) complexation

Co-reporter:Monika Ali Khan, John P. Lowe, Andrew L. Johnson, Alan J. W. Stewart and Simon E. Lewis

Chemical Communications 2011 vol. 47(Issue 1) pp:215-217

Publication Date(Web):20 Aug 2010

DOI:10.1039/C0CC01169J

A cyclohexadiene ligand prepared by microbial arene 1,2-dihydroxylation undergoes spontaneous rearrangement upon complexation to tricarbonyliron(0). Subsequent iron removal affords a novel route to formal arene 2,3-dihydroxylation products enantiomeric to those obtainable by direct microbial arene oxidation.

“Inosaminoacids”: novel inositol–amino acid hybrid structures accessed by microbial arene oxidation

Co-reporter:Sarah Pilgrim, Gabriele Kociok-Köhn, Matthew D. Lloyd and Simon E. Lewis

Chemical Communications 2011 vol. 47(Issue 16) pp:4799-4801

Publication Date(Web):15 Mar 2011

DOI:10.1039/C1CC10643K

Microbial 1,2-dihydroxylation of sodium benzoate permits the rapid construction of novel inositol–amino acid hybrid structures. Both β- and γ-amino acids are accessible by means of an acylnitroso Diels–Alder cycloaddition.

Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds

Co-reporter:Julia A. Griffen, Amélie M. Le Coz, Gabriele Kociok-Köhn, Monika Ali Khan, Alan J. W. Stewart and Simon E. Lewis

Organic & Biomolecular Chemistry 2011 vol. 9(Issue 10) pp:3920-3928

Publication Date(Web):06 Apr 2011

DOI:10.1039/C1OB05131H

Metabolism of meta-bromobenzoic acid by the blocked mutant Ralstonia eutrophus B9 affords an enantiopure dearomatised halodiene-diol which we demonstrate is a versatile chiron for organic synthesis. The presence of the halogen leads to reactivity that is distinct to that observed for the non-halogenated analogue and also serves as a synthetic handle for further functionalisation.

Iron(0) Tricarbonyl Complexes of Microbially Derived Cyclohexadiene Ligands Containing Quaternary Stereocenters

Co-reporter:Monika Ali Khan, Mary F. Mahon, Alan J. W. Stewart and Simon E. Lewis

Organometallics 2010 Volume 29(Issue 1) pp:199-204

Publication Date(Web):November 25, 2009

DOI:10.1021/om9009069

Tricarbonyliron(0) complexes of novel cyclohexadiene ligands possessing quaternary centers have been synthesized and characterized by 1H and 13C NMR and by X-ray crystallography. The ligands, which are derived via an unusual microbial oxidation of benzoic acid, have been shown to undergo oxidative modification postcomplexation. The factors that influence facial discrimination upon complexation are discussed.

“Inosaminoacids”: novel inositol–amino acid hybrid structures accessed by microbial arene oxidation

Co-reporter:Sarah Pilgrim, Gabriele Kociok-Köhn, Matthew D. Lloyd and Simon E. Lewis

Chemical Communications 2011 - vol. 47(Issue 16) pp:NaN4801-4801

Publication Date(Web):2011/03/15

DOI:10.1039/C1CC10643K

Accessing the antipodal series in microbial arene oxidation: a novel diene rearrangement induced by tricarbonyliron(0) complexation

Co-reporter:Monika Ali Khan, John P. Lowe, Andrew L. Johnson, Alan J. W. Stewart and Simon E. Lewis

Chemical Communications 2011 - vol. 47(Issue 1) pp:NaN217-217

Publication Date(Web):2010/08/20

DOI:10.1039/C0CC01169J

Expanding the chiral pool: oxidation of meta-bromobenzoic acid by R. eutrophus B9 allows access to new reaction manifolds

Co-reporter:Julia A. Griffen, Amélie M. Le Coz, Gabriele Kociok-Köhn, Monika Ali Khan, Alan J. W. Stewart and Simon E. Lewis

Organic & Biomolecular Chemistry 2011 - vol. 9(Issue 10) pp:NaN3928-3928

Publication Date(Web):2011/04/06

DOI:10.1039/C1OB05131H

Aliphatic C–H activation with aluminium trichloride–acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons

Co-reporter:Catherine L. Lyall, Mario Uosis-Martin, John P. Lowe, Mary F. Mahon, G. Dan Pantoş and Simon E. Lewis

Organic & Biomolecular Chemistry 2013 - vol. 11(Issue 9) pp:NaN1475-1475

Publication Date(Web):2012/12/21

DOI:10.1039/C2OB26765A

Direct core functionalisation of naphthalenediimides by iridium catalysed C–H borylation

Co-reporter:Catherine L. Lyall, Camilla C. Shotton, Monserrat Pérez-Salvia, G. Dan Pantoş and Simon E. Lewis

Chemical Communications 2014 - vol. 50(Issue 89) pp:NaN13840-13840

Publication Date(Web):2014/09/18

DOI:10.1039/C4CC06522K

Benzoate dioxygenase from Ralstonia eutropha B9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons

Co-reporter:Julia A. Griffen, Sarah J. Kenwright, Sarah Abou-Shehada, Scott Wharry, Thomas S. Moody and Simon E. Lewis

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 1) pp:NaN90-90

Publication Date(Web):2014/01/08

DOI:10.1039/C3QO00057E

Oxidation of benzoic acid by a microorganism expressing benzoate dioxygenase leads to the formation of an unusual ipso, ortho arene cis-diol in sufficient quantities to be useful for synthesis. This homochiral diol possesses an array of differentiated functionality which can be exploited to access diverse highly oxygenated structures by concise synthetic sequences.