Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores

Dominic Taylor, Thomas Malcomson, Adilet Zhakeyev, Georgina Margaret Rosair, Martin J. Paterson, Jose Marques-Hueso, Scott J. Dalgarno*, Filipe Vilela*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Regioselective stepwise phenylation of 4,7-diarylbenzo[c][1,2,5]thiadiazole fluorophores has been achieved through a facile one-pot, three-step synthetic strategy involving sequential borylation, hydroxydechlorination and Suzuki–Miyaura cross-coupling reactions. Crucial to the selectivity was the use of BCl3 to regioselectively install a boronic acid group in the ortho-position of only one of the diaryl groups. The subsequent introduction of ortho-phenyl groups through Suzuki–Miyaura cross-coupling gave rise to twisted structures with hindered intramolecular rotation, providing a structural lever with which the fluorophore absorption and emission properties could be adjusted.
Original languageEnglish
Pages (from-to)5826-5832
Number of pages7
JournalRSC Advances
Volume13
Issue number9
Early online date16 Feb 2023
DOIs
Publication statusPublished - 2023

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