October 9, 2025Open Access

Cascade C–H Halogenation of Tetraazapyrene with Iodine Halides

Key Points

Cascade halogenation efficiently alters LUMO energy levels in tetraazapyrene derivatives, enhancing control.
The reaction yields chlorinated and heterohalogenated derivatives, with potential applications in organic electronics.
Using iodine halides as a reagent allows for selective halogenation, optimizing electronic properties and material design.
Findings suggest innovative pathways for developing tetraazapyrene-based materials with tailored electronic features.

Abstract

Iodine halide as an efficient and selective halogenation reagent is presented for the cascade halogenation of an electron-deficient tetraazapyrene (TAP), yielding both chlorinated and heterohalogenated derivatives. This approach enables precise control over the LUMO energy levels of the resulting TAPs by varying the type and extent of halogenation, offering a powerful strategy for fine-tuning their electronic properties. These findings open new avenues for the rational design of TAP-based materials in organic molecular electronics.

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