Journal article Open Access

Revealing resonance effects and intramolecular dipole interactions in the positional isomers of benzonitrile-core thermally activated delayed fluorescence materials

Nadzeya A. Kukhta; Heather F. Higginbotham; Tomas Matulaitis; Andrew Danos; Aisha N. Bismillah; Nils Haase; Marc K. Etherington; Dmitry S. Yufit; Paul R. McGonigal; Juozas Vidas Gražulevičius; Andrew P. Monkman

We report on the properties of the three positional isomers of (2,7-di-tert-butyl-9,9-dimethylacridin-10(9H)-yl)benzonitrile, which are found to have comparable donor steric environments and donor–acceptor dihedral angles. An unexpected intramolecular dipole interaction imparts a unique molecular geometry to the ortho-linked isomer, while comparison of the meta- and para-isomers uncovers how positional differences in acceptor strengths (a consequence of differences in aromatic π-system electron density) lead to very different triplet harvesting and emission properties. These positional-isomer effects on TADF follow the well-known aromatic directing rules from organic synthesis, in keeping with their common origin arising from contributions of multiple electronic resonance structures. Understanding these positional effects and methods of dihedral control is critical to the future design of efficient TADF emitters.

Files (4.0 MB)
Name Size
c9tc02742d.pdf
md5:5ffed7cc360329733218d3fc01734035
4.0 MB Download
6
11
views
downloads
Views 6
Downloads 11
Data volume 44.2 MB
Unique views 6
Unique downloads 11

Share

Cite as