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4 article(s) from Jones, David J.

An improved synthesis of adefovir and related analogues

David J. Jones,
Eileen M. O’Leary and
Timothy P. O’Sullivan

Beilstein J. Org. Chem. 2019, 15, 801–810, doi:10.3762/bjoc.15.77

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Figure 1: Adefovir (1) and its prodrug 2.

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Scheme 1: Literature syntheses of 1.

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Figure 2: Retrosynthetic analysis of 6 to synthons 9 and 10.

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Scheme 2: Forward synthesis of 6 from 9 and 10.

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Figure 3: Retrosynthesis of 6 to synthons 14 and 3.

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Scheme 3: Application of related alkyl iodide 15 [52].

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Scheme 4: Synthesis of 6 and 20 via iodide 14.

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Scheme 5: Synthesis of phosphonate 6 using novel salt 21.

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Scheme 6: Application of iodide 14 in the synthesis of adefovir analogues.

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Figure 4: HMBC spectrum confirms N7-selectivity for the major product 29.

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Scheme 7: Attempted synthesis of adefovir dipivoxil (2) exploiting phosphonate 33.

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Published 29 Mar 2019

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High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

Paul B. Geraghty,
Calvin Lee,
Jegadesan Subbiah,
Wallace W. H. Wong,
James L. Banal,
Mohammed A. Jameel,
Trevor A. Smith and
David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

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Figure 1: Chemical structures of molecular materials with the following variations; BT^xR, alkyl side chains o...

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Scheme 1: Synthesis of the key intermediates TMS-T_x-BPin (3), i) diisopropylamine (DIA), THF, n-BuLi, −78 °C ...

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Scheme 2: Oligothiophenes 4–11 synthesised through reaction of the commercially available 5-bromo-2-thiophene...

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Scheme 3: Synthesis of the bithiophene through palladium catalyzed direct arylation, a) i) Pd(OAc)₂, PCy₃, Pi...

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Scheme 4: Synthesis of the key bis-borylated BDT core 13, i) 1.5 equiv B₂Pin₂, 0.025 equiv [Ir(COD)OMe]₂, 0.0...

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Scheme 5: Synthesis of the BXR and BT^XR series of materials, i) 5-bromothiophene carboxaldehyde, 5b, 7a–c, 9b...

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Figure 2: BQR thermal and POM properties. a) DSC thermogram of BQR under nitrogen at a ramp rate of 10 °C min...

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Figure 3: BT⁴R thermal and POM images. a) DSC thermogram of BT⁴R under nitrogen at a ramp rate of 10 °C min⁻¹...

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Figure 4: UV–vis absorption spectra of the BX^XR series in CHCl₃. An expansion of the peak area is shown in th...

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Figure 5: Normalised thin film UV–vis absorption profiles for the BX^xR series for, a) as-cast films (from CDCl...

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Figure 6: Normalised thin film UV–vis absorption profiles for a) BBR, b) BTR and c) BQR showing as-cast (blac...

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Figure 7: Normalised thin film fluorescence emission profiles for BX^xR series after excitation at 580 nm, a) ...

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Figure 8: Variable temperature thin film UV–vis absorption profiles for BQR, collected using the transmission...

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Figure 9: Variable temperature thin-film fluorescence emission profiles for BQR, a) heating and b) cooling, c...

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Figure 10: BQR thin film UV–vis (solid lines) and fluorescence emission spectra (dashed lines) collected at rt...

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Figure 11: Optimized geometry and molecular orbital surfaces of HOMO (bottom) and LUMO (top) for the BXR serie...

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Figure 12: J–V characteristics of BXR:PC₇₁BM BHJ solar cells. (a) device structure, (b) J–V curves for as-cast...

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Figure 13: J–V characteristics of BT^xR:PC₇₁BM ternary BHJ solar cells, a) device architecture, and b) J–V curv...

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Figure 14: J–V characteristics of PTB7-Th:BQR:PC₇₁BM ternary BHJ solar cells. (a) PTB7-Th chemical structure, ...

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Published 02 Nov 2016

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Separation and identification of indene–C₇₀ bisadduct isomers

Bolong Zhang,
Jegadesan Subbiah,
David J. Jones and
Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

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Figure 1: Molecular structure of IC₆₀BA and IC₇₀BA.

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Figure 2: a) Schlegel diagram of C₇₀; b) illustrations of three regioisomers of IC₇₀BA and their geometrical ...

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Figure 3: Chromatograms of IC₇₀BA mixture and fractions 1, 4 and 9 separated by HPLC (Cosmosil Buckyprep-D co...

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Figure 4: ¹H NMR spectrum of IC₇₀BA fractions containing a major isomer species.

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Figure 5: The retention time of the first species in fraction 10 is shorter than the species in fraction 11 o...

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Figure 6: The UV–vis spectrum of each fraction of IC₇₀BA as well as known C₇₀ bisadducts: a) fraction 1, 2, 3...

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Figure 7: Schematic diagram of the architecture of BHJ solar cell devices (a) and J−V curves of the devices c...

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Published 06 May 2016

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Controlled synthesis of poly(3-hexylthiophene) in continuous flow

Helga Seyler,
Jegadesan Subbiah,
David J. Jones,
Andrew B. Holmes and
Wallace W. H. Wong

Beilstein J. Org. Chem. 2013, 9, 1492–1500, doi:10.3762/bjoc.9.170

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Scheme 1: (a) Preparation of thiophene Grignard monomer and synthesis of P3HT by Kumada catalyst transfer pol...

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Figure 1: Plot of number-average molecular weight, M_n, versus monomer–catalyst ratio [M]₀/[I]₀ for batch and ...

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Figure 2: MALDI mass spectrum of low-molecular-weight preparation (GPC, M_n = 6.2 kg/mol) of P3HT in continuou...

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Figure 3: Plot of number-average molecular weight, M_n, versus monomer–catalyst ratio [M]₀/[I]₀ for batch and ...

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Scheme 2: Schematic representation of the telescoped preparation of P3HT in a flow reactor.

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Figure 4: ¹H NMR (CDCl₃, 500 MHz) spectra of P3HT samples prepared in (a) flow and (b) batch show comparable ...

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Figure 5: (a) Schematic diagram of the photovoltaic device geometry and (b) J–V curves of BHJ solar cells wit...

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Published 25 Jul 2013

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An improved synthesis of adefovir and related analogues

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

Separation and identification of indene–C70 bisadduct isomers

Controlled synthesis of poly(3-hexylthiophene) in continuous flow

Separation and identification of indene–C₇₀ bisadduct isomers