Synthesis and Characterization of Novel Pyrene Derivatives Containing Thienyl Groups

Abstract

New thiophene modified pyrene derivatives 4,5,9,10-tetra(2-thienyl)-2,7-di-tert-butylpyrene (TTP) and 4,5,9,10-tetra(2-(5-hexyl)thienyl)-2,7-di-tert-butylpyrene (THTP) have been designed and synthesized by Friedel-Crafts alkylation reaction, bromination, Stille Coupling reaction of pyrene, and so on. The optical band gaps of the TTP and THTP determined from the absorption onsets were 3.21 and 3.10 eV, respectively. The energy levels for highest occupied molecular orbital (E_HOMO) were determined from their cyclic voltammograms to be −5.84 and −5.68 eV, respectively. The relatively large band gaps and low E_HOMO levels imply that these materials have high stability against photo-degradation, and may be promising candidates for stable hole-transporting materials.

Keywords:

• Organic semiconductor
• pyrene
• synthesis
• thiophene

Acknowledgment

The devices investigated in this work were fabricated in the Micro Functional Device Research Center of the College of Science and Technology, Nihon University.

Notes

*LUMO levels were determined by adding and HOMO energies.