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

Taylor, Dominic and Malcomson, Thomas and Zhakeyev, Adilet and Rosair, Georgina M and Paterson, Martin J and Marques-Hueso, Jose and Dalgarno, Scott J and Vilela, Filipe (2023) Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores. RSC Advances, 13 (9). pp. 5826-5832. ISSN 2046-2069

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Abstract

Regioselective stepwise phenylation of 4,7-diarylbenzo[ ][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 BCl to regioselectively install a boronic acid group in the -position of only one of the diaryl groups. The subsequent introduction of -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.

Item Type:
Journal Article
Journal or Publication Title:
RSC Advances
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1500/1500
Subjects:
?? general chemical engineeringgeneral chemistrychemical engineering(all)chemistry(all) ??
ID Code:
188850
Deposited By:
Deposited On:
15 Mar 2023 09:45
Refereed?:
Yes
Published?:
Published
Last Modified:
20 Aug 2024 11:45