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C−H Borylation/Cross‐Coupling Forms Twisted Donor–Acceptor Compounds Exhibiting Donor‐Dependent Delayed Emission
Author(s) -
Crossley Daniel L.,
Kulapichitr Pakapol,
Radcliffe James E.,
Dunsford Jay J.,
VitoricaYrezabal Inigo,
Kahan Rachel J.,
Woodward Adam W.,
Turner Michael L.,
McDouall Joseph J. W.,
Ingleson Michael J.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801799
Subject(s) - borylation , triphenylamine , excited state , moiety , chemistry , intramolecular force , acceptor , photochemistry , suzuki reaction , boron , stereochemistry , organic chemistry , catalysis , palladium , aryl , atomic physics , alkyl , physics , condensed matter physics
Benzothiadiazole (BT) directed C−H borylation using BCl 3 , 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 S 1 /T 2 excited states, which are predominantly intramolecular charge‐transfer states, and the T 1 excited state, which is predominantly a local excited state on the BT acceptor moiety.