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Allenes as Stimuli-Responsive Chromophores for Visible to Near-Infrared Optical Modulation.

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Tetraarylallenes exhibit reversible protonation, leading to significant optical changes. This discovery unlocks allenes as a versatile platform for tunable, stimuli-responsive materials in the visible to near-infrared spectrum.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photophysics

Background:

  • Allenes, despite their unique π-systems and synthetic versatility, are underutilized in functional material design.
  • Stimuli-responsive materials are crucial for advanced optical applications.

Purpose of the Study:

  • To explore the protonation behavior of tetraaryl-substituted allenes.
  • To investigate the structure-property relationships governing their optoelectronic responses.
  • To establish allenes as a platform for reversible optical modulation.

Main Methods:

  • Synthesis of five tetraarylallene derivatives.
  • Protonation studies using various acids.
  • UV-vis-NIR spectroscopy and ultrafast transient absorption spectroscopy.
  • Frontier molecular orbital (FMO) analysis and time-dependent density functional theory (TD-DFT) calculations.

Main Results:

  • Tetraarylallenes undergo clean and reversible protonation at the central carbon.
  • Protonation induces large bathochromic shifts (up to 500 nm) with high extinction coefficients in the near-infrared region.
  • TD-DFT calculations reveal polymethine-like electronic structures with tunable donor-acceptor character upon protonation.
  • Reversible protonation/deprotonation confirmed, even with weak acids like acetic acid.

Conclusions:

  • Allenes provide a synthetically accessible platform for reversible, stimuli-responsive optical modulation.
  • Protonation triggers significant π-electron reorganization, enabling tunable optoelectronic properties.
  • The findings open new avenues for designing advanced functional materials based on allene chemistry.