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

Daniel L. Crossley, Pakapol Kulapichitr, James E. Radcliffe, Jay J. Dunsford, Inigo Vitorica-Yrezabal, Rachel J. Kahan, Adam W. Woodward, Michael L. Turner*, Joseph J.W. McDouall, Michael J. Ingleson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)10521-10530
Number of pages10
JournalChemistry - A European Journal
Volume24
Issue number41
Early online date21 May 2018
DOIs
Publication statusE-pub ahead of print - 21 May 2018

Keywords

  • benzothiadiazole
  • boron
  • borylation
  • natural transition orbitals
  • thermally activated delayed fluorescence

Fingerprint Dive into the research topics of 'C−H Borylation/Cross-Coupling Forms Twisted Donor–Acceptor Compounds Exhibiting Donor-Dependent Delayed Emission'. Together they form a unique fingerprint.

Cite this