Synthesis of 2,5,8-Tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzo[1,2-b:3,4-b′:5,6-b″] Trithiophenes and Their Spontaneous Orientation Polarization in Thin Films

Wei Chih Wang, Kyohei Nakano, Chain Shu Hsu*, Keisuke Tajima*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

To investigate the relationship between molecular structures and spontaneous orientation polarization (SOP) in organic thin films, 2,5,8-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzo[1,2-b:3,4-b′:5,6-b″] trithiophene (TPBTT) and its ethyl derivative (m-ethyl-TPBTT) were synthesized. Variable angle spectroscopic ellipsometry and two-dimensional grazing-incidence wide-angle X-ray scattering showed that the vacuum-deposited films of TPBTT and m-ethyl-TPBTT had a higher degree of molecular orientation parallel to the substrate compared with that of prototypical 2,2′,2″-(1,3,5-benzinetriyl)-tris(1-phenyl-1-H-benzimidazole) (TPBi) due to the larger π-conjugated benzotrithiophene core. However, TPBTT films showed a lower SOP of +54.4 mV/nm than did the TPBi film (+77.3 mV/nm), indicating that the molecular orientation alone did not determine the SOP. In contrast, m-ethyl-TPBTT showed a larger SOP of +104.0 mV/nm in the film. Quantum chemical calculations based on density functional theory suggested that the differences in the stable molecular conformation and the permanent dipole moments between TPBTT and m-ethyl-TPBTT caused the differences in SOP. These results suggest that the simultaneous control of the orientational order and conformation of the molecules is important to achieving a large SOP in films.

Original languageEnglish
Pages (from-to)20294-20301
Number of pages8
JournalACS Applied Materials and Interfaces
Volume15
Issue number16
DOIs
StatePublished - 26 Apr 2023

Keywords

  • dipole moment
  • electret generators
  • giant surface potential
  • molecular orientation
  • spontaneous orientation polarization

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