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Electronic structure modifications induced by increased molecular complexity: from triphenylamine to m-MTDATA.

T Zhang1, I E Brumboiu, V Lanzilotto

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The electronic structure of starburst molecule m-MTDATA was studied using spectroscopy and DFT. Its enhanced electron-donating properties stem from increased nitrogen atoms, leading to a smaller HOMO-LUMO gap compared to triphenylamine.

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Area of Science:

  • Materials Science
  • Physical Chemistry
  • Organic Electronics

Background:

  • Starburst molecule 4,4',4''-tris(N-3-methylphenyl-N-phenyl-amino)triphenylamine (m-MTDATA) is crucial in optoelectronics due to its electron-donor properties.
  • Triphenylamine (TPA) is a foundational building block for m-MTDATA, with its electronic structure well-studied.

Purpose of the Study:

  • Investigate the gas-phase electronic structure of m-MTDATA for the first time.
  • Compare the electronic properties of m-MTDATA with TPA to understand the effect of molecular size and nitrogen content.
  • Provide a comprehensive description of m-MTDATA's molecular electronic structure.

Main Methods:

  • Photoelectron Spectroscopy (PES) for electronic structure analysis.
  • Near Edge X-ray Absorption Fine Structure (NEXAFS) spectroscopy.
  • Density Functional Theory (DFT) calculations to complement experimental data.

Main Results:

  • C 1s photoelectron spectra of m-MTDATA and TPA show similarities due to competing electronegativity and lone-pair delocalization effects.
  • m-MTDATA exhibits a distinct three-peak feature in the valence binding energy region, attributed to N 2pz orbitals from increased nitrogen content.
  • A reduced HOMO-LUMO gap was observed for m-MTDATA, indicating enhanced electron-donating capabilities compared to TPA.

Conclusions:

  • The electronic structure of m-MTDATA is well-described by combining PES, NEXAFS, and DFT.
  • Increasing molecular size and nitrogen content in m-MTDATA significantly impacts its electronic properties, particularly enhancing electron donation.
  • m-MTDATA presents improved optoelectronic potential over TPA due to its modified electronic structure and lower HOMO-LUMO gap.