Issue 22, 2022

Molecular mechanism of rigidity- and planarity-promoted, state-dependent doping of conjugated ladder-type molecules

Abstract

Determining the doping mechanism of organic semiconductors (OSCs) using neutral dopants, whether through the formation of an ion-pair (IP) or a charge transfer complex (CTC), remains an open challenge. It is hypothesized that the rigidity and planarity of the π-backbone of OSCs can significantly impact their doping mechanism and efficiency. In this work, a series of fused-ring ladder-type small molecules (B-ICz, Th-ICz, and BDT-ICz) are synthesized as models to investigate this hypothesis. Upon mixing with the electron-deficient dopant F4TCNQ, each of these compounds shows dominant IP formation in solution whereas both IPs and CTCs are observed in the solid-state. Control experiments and computational investigations reveal that the extended, rigid, and coplanar π-faces of these ladder-type molecules are essential to facilitate the doping interaction with F4TCNQ, for both IP and CTC mechanisms. This work provides principles for the future rational design of molecular structures of OSCs and dopants for electronic doping purposes.

Graphical abstract: Molecular mechanism of rigidity- and planarity-promoted, state-dependent doping of conjugated ladder-type molecules

Supplementary files

Article information

Article type
Research Article
Submitted
05 Ago 2022
Accepted
15 Sep 2022
First published
16 Sep 2022

Mater. Chem. Front., 2022,6, 3329-3337

Molecular mechanism of rigidity- and planarity-promoted, state-dependent doping of conjugated ladder-type molecules

J. Lee, S. Li, X. Ji, S. Che, Y. Cao, D. P. Tabor and L. Fang, Mater. Chem. Front., 2022, 6, 3329 DOI: 10.1039/D2QM00789D

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