Chemistry A European J - 2022 - Panther - Solvent%E2%80%90Free Synthesis of Core%E2%80%90Functionalised Naphthalene Diimides by Using a.pdf (6.42 MB)
Solvent-free synthesis of core-functionalised naphthalene diimides by using a vibratory ball mill: Suzuki, Sonogashira and Buchwald–Hartwig reactions
journal contribution
posted on 2023-06-15, 20:43 authored by Lydia A Panther, Daniel GuestDaniel Guest, Andrew McGownAndrew McGown, Hugo Emerit, Raysa K Tareque, Arathy Jose, Chris M Dadswell, SimonJ Coles, Graham J Tizzard, Ramon González-Méndez, Charles AI Goodall, Mark BagleyMark Bagley, John SpencerJohn Spencer, Barnaby GreenlandBarnaby GreenlandSolvent-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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Publication status
- Published
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- Published version
Journal
Chemistry - A European JournalISSN
0947-6539Publisher
WileyExternal DOI
Issue
49Volume
28Page range
e202201444 1-12Event location
GermanyDepartment affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes
Legacy Posted Date
2022-10-18First Open Access (FOA) Date
2022-10-18First Compliant Deposit (FCD) Date
2022-10-18Usage metrics
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