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

Chemistry

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https://doi.org/10.1039/d2ra08319a
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Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores. / Taylor, Dominic; Malcomson, Thomas; Zhakeyev, Adilet et al.
In: RSC Advances, Vol. 13, No. 9, 16.02.2023, p. 5826-5832.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Bibtex

@article{7f9780680a7c4f5e85a467375bc4c5cb,

title = "Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores",

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. ",

author = "Dominic Taylor and Thomas Malcomson and Adilet Zhakeyev and Rosair, {Georgina M} and Paterson, {Martin J} and Jose Marques-Hueso and Dalgarno, {Scott J} and Filipe Vilela",

year = "2023",

month = feb,

day = "16",

doi = "10.1039/d2ra08319a",

language = "English",

volume = "13",

pages = "5826--5832",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "9",

}

RIS

TY - JOUR

T1 - Regioselective electrophilic aromatic borylation as a method for synthesising sterically hindered benzothiadiazole fluorophores

AU - Taylor, Dominic

AU - Malcomson, Thomas

AU - Zhakeyev, Adilet

AU - Rosair, Georgina M

AU - Paterson, Martin J

AU - Marques-Hueso, Jose

AU - Dalgarno, Scott J

AU - Vilela, Filipe

PY - 2023/2/16

Y1 - 2023/2/16

N2 - 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.

AB - 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.

U2 - 10.1039/d2ra08319a

DO - 10.1039/d2ra08319a

M3 - Journal article

C2 - 36846398

VL - 13

SP - 5826

EP - 5832

JO - RSC Advances

JF - RSC Advances

SN - 2046-2069

IS - 9

ER -

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