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1,3,6,8-Tetraazapyrenes: synthesis, solid-state structures, and properties as redox-active materials.

Sonja Geib¹, Susanne C Martens, Ute Zschieschang

¹Anorganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany.

The Journal of Organic Chemistry

|June 27, 2012

Summary

New tetraazapyrene (TAPy) derivatives were synthesized and characterized. These novel organic compounds show promise as n-type semiconductors for organic field-effect transistors (OFETs).

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Area of Science:

Organic Chemistry
Materials Science
Nanoscience

Background:

Tetraazapyrene (TAPy) derivatives are explored for their electronic properties.
Synthesis and functionalization of TAPy molecules are crucial for tuning their semiconductor behavior.

Purpose of the Study:

To synthesize novel tetraazapyrene (TAPy) derivatives.
To investigate the electronic properties and semiconductor potential of these new TAPy compounds.

Main Methods:

Synthesis via reduction of tetranitronaphthalene and reaction with anhydrides.
Derivatization through chlorination and bromination, followed by Suzuki cross-coupling.
Characterization using single-crystal X-ray analysis, DFT modeling, and cyclic voltammetry.

Main Results:

Successful synthesis of 2,7-disubstituted TAPy derivatives and core-halogenated analogs.
Polymorphism observed in some TAPy compounds.
Calculated and experimentally verified LUMO energy levels ranging from -3.57 to -4.14 eV.
Demonstrated potential as n-type semiconductors in organic field-effect transistors (OFETs).

Conclusions:

The synthesized TAPy derivatives exhibit tunable electronic properties.
These compounds are promising candidates for n-type organic semiconductor applications.