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C-H Borylation/Cross-Coupling Forms Twisted Donor-Acceptor Compounds Exhibiting Donor-Dependent Delayed Emission.


ABSTRACT: Benzothiadiazole (BT) directed C-H borylation using BCl3 , followed by B-Cl hydrolysis and Suzuki-Miyaura cross-coupling enables facile access to twisted donor-acceptor compounds. A subsequent second C-H borylation step provides, on arylation of boron, access to borylated highly twisted D-A compounds with a reduced bandgap, or on B-Cl hydrolysis/cross-coupling to twisted D-A-D compounds. Photophysical studies revealed that in this series there is long lifetime emission only when the donor is triphenylamine. Computational studies indicated that the key factor in observing the donor dependent long lifetime emission is the energy gap between the S1 /T2 excited states, which are predominantly intramolecular charge-transfer states, and the T1 excited state, which is predominantly a local excited state on the BT acceptor moiety.

SUBMITTER: Crossley DL 

PROVIDER: S-EPMC6099339 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

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C-H Borylation/Cross-Coupling Forms Twisted Donor-Acceptor Compounds Exhibiting Donor-Dependent Delayed Emission.

Crossley Daniel L DL   Kulapichitr Pakapol P   Radcliffe James E JE   Dunsford Jay J JJ   Vitorica-Yrezabal Inigo I   Kahan Rachel J RJ   Woodward Adam W AW   Turner Michael L ML   McDouall Joseph J W JJW   Ingleson Michael J MJ  

Chemistry (Weinheim an der Bergstrasse, Germany) 20180625 41


Benzothiadiazole (BT) directed C-H borylation using BCl<sub>3</sub> , followed by B-Cl hydrolysis and Suzuki-Miyaura cross-coupling enables facile access to twisted donor-acceptor compounds. A subsequent second C-H borylation step provides, on arylation of boron, access to borylated highly twisted D-A compounds with a reduced bandgap, or on B-Cl hydrolysis/cross-coupling to twisted D-A-D compounds. Photophysical studies revealed that in this series there is long lifetime emission only when the d  ...[more]

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