Issue 4, 2023

Fused-ring molecules based on B ← N and imide units with low energy levels

Abstract

The general strategy to design n-type organic semiconductors is to introduce electron-withdrawing moieties, such as sp2-hybridized N atoms, cyano groups, imide units, a boron–nitrogen coordination bond (B ← N), and halogen substituents, to π-conjugated skeletons. In this work, for the first time, we report n-type polycyclic aromatic hydrocarbons (PAHs) incorporated with both B ← N and imide units. By changing the positions of the two B ← N units, we synthesize a centrosymmetric PAH molecule and an axisymmetric PAH molecule. Both the molecules have a planar configuration, which is beneficial for close π-stacking in the solid state, and thus for charge transport. The centrosymmetric molecule has a net dipole moment of zero, while the axisymmetric molecule has a net dipole moment of 3.20 Debye with intramolecular charge transfer characteristics. The two isomeric molecules exhibit deep-lying LUMO and HOMO energy levels of −4.04 eV/−5.78 eV and −4.12 eV/−5.95 eV, respectively, which are much lower than those of n-type molecules containing only two B ← N units or two imide units reported in the literature studies.

Graphical abstract: Fused-ring molecules based on B ← N and imide units with low energy levels

Supplementary files

Article information

Article type
Research Article
Submitted
30 nov 2022
Accepted
29 dez 2022
First published
30 dez 2022

Org. Chem. Front., 2023,10, 923-927

Fused-ring molecules based on B ← N and imide units with low energy levels

R. Liu, J. Hu, Y. Min and J. Liu, Org. Chem. Front., 2023, 10, 923 DOI: 10.1039/D2QO01900K

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