Solvent-free synthesis of core-functionalised naphthalene diimides by using a Vibratory Ball Mill: Suzuki, Sonogashira and Buchwald–Hartwig reactions
Solvent-free synthesis of core-functionalised naphthalene diimides by using a Vibratory Ball Mill: Suzuki, Sonogashira and Buchwald–Hartwig reactions
Solvent-free synthesis by using a vibratory ball mill (VBM) offers the chance to access new chemical reactivity, whilst reducing solvent waste and minimising reaction times. Herein, we report the core functionalisation of N,N’-bis(2-ethylhexyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid (Br2-NDI) by using Suzuki, Sonogashira and Buchwald–Hartwig coupling reactions. The products of these reactions are important building blocks in many areas of organic electronics including organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs) and organic photovoltaic cells (OPVCs). The reactions proceed in as little as 1 h, use commercially available palladium sources (frequently Pd(OAc)2) and are tolerant to air and atmospheric moisture. Furthermore, the real-world potential of this green VBM protocol is demonstrated by the double Suzuki coupling of a monobromo(NDI) residue to a bis(thiophene) pinacol ester. The resulting dimeric NDI species has been demonstrated to behave as an electron acceptor in functioning OPVCs.
ball milling, core-functionalised naphthalene diimide, coupling reactions, green chemistry, solid-phase synthesis
Panther, Lydia A.
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Guest, Daniel P.
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McGown, Andrew
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Emerit, Hugo
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Tareque, Raysa Khan
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Jose, Arathy
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Dadswell, Chris M.
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Coles, Simon J.
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Tizzard, Graham J.
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González-Méndez, Ramón
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Goodall, Charles A.I.
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Bagley, Mark C.
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Spencer, John
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Greenland, Barnaby W.
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1 September 2022
Panther, Lydia A.
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Guest, Daniel P.
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McGown, Andrew
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Emerit, Hugo
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Tareque, Raysa Khan
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Jose, Arathy
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Dadswell, Chris M.
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Coles, Simon J.
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Tizzard, Graham J.
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González-Méndez, Ramón
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Goodall, Charles A.I.
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Bagley, Mark C.
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Spencer, John
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Greenland, Barnaby W.
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Panther, Lydia A., Guest, Daniel P., McGown, Andrew, Emerit, Hugo, Tareque, Raysa Khan, Jose, Arathy, Dadswell, Chris M., Coles, Simon J., Tizzard, Graham J., González-Méndez, Ramón, Goodall, Charles A.I., Bagley, Mark C., Spencer, John and Greenland, Barnaby W.
(2022)
Solvent-free synthesis of core-functionalised naphthalene diimides by using a Vibratory Ball Mill: Suzuki, Sonogashira and Buchwald–Hartwig reactions.
Chemistry - A European Journal, 28 (49), [e202201444].
(doi:10.1002/chem.202201444).
Abstract
Solvent-free synthesis by using a vibratory ball mill (VBM) offers the chance to access new chemical reactivity, whilst reducing solvent waste and minimising reaction times. Herein, we report the core functionalisation of N,N’-bis(2-ethylhexyl)-2,6-dibromo-1,4,5,8-naphthalenetetracarboxylic acid (Br2-NDI) by using Suzuki, Sonogashira and Buchwald–Hartwig coupling reactions. The products of these reactions are important building blocks in many areas of organic electronics including organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs) and organic photovoltaic cells (OPVCs). The reactions proceed in as little as 1 h, use commercially available palladium sources (frequently Pd(OAc)2) and are tolerant to air and atmospheric moisture. Furthermore, the real-world potential of this green VBM protocol is demonstrated by the double Suzuki coupling of a monobromo(NDI) residue to a bis(thiophene) pinacol ester. The resulting dimeric NDI species has been demonstrated to behave as an electron acceptor in functioning OPVCs.
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Chemistry A European J - 2022 - Panther - Solvent‐Free Synthesis of Core‐Functionalised Naphthalene Diimides by Using a
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Accepted/In Press date: 27 May 2022
e-pub ahead of print date: 27 May 2022
Published date: 1 September 2022
Additional Information:
Funding Information:
The University of Sussex is thanked for funding a studentship (L.A.P.). We acknowledge financial support from the ERDF: LabFact: InterReg V project 121; (B.W.G, J.S., M.C.B., H.E., R.K.T., A.J., D.P.G., A.M.), EPSRC (EP/P026990/1; J.S.), Sussex HEIF Covid Emergency Funds (D.P.G.) and EPSRC for the National Crystallography Service at Southampton (G.J.T., S.J.C.). [53]
Publisher Copyright:
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Keywords:
ball milling, core-functionalised naphthalene diimide, coupling reactions, green chemistry, solid-phase synthesis
Identifiers
Local EPrints ID: 470092
URI: http://eprints.soton.ac.uk/id/eprint/470092
ISSN: 0947-6539
PURE UUID: b3af9a2f-cfbd-4ed4-9493-c41e781007db
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Date deposited: 03 Oct 2022 16:48
Last modified: 18 Mar 2024 02:54
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Contributors
Author:
Lydia A. Panther
Author:
Daniel P. Guest
Author:
Andrew McGown
Author:
Hugo Emerit
Author:
Raysa Khan Tareque
Author:
Arathy Jose
Author:
Chris M. Dadswell
Author:
Ramón González-Méndez
Author:
Charles A.I. Goodall
Author:
Mark C. Bagley
Author:
John Spencer
Author:
Barnaby W. Greenland
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