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Area of Science:

  • Photophysics and photochemistry
  • Organic chemistry
  • Computational chemistry

Background:

  • The rotational dynamics of tolanes along their acetylene axis remain incompletely understood.
  • Investigating the impact of conformational changes on the optical and electronic properties of tolanes is crucial.

Purpose of the Study:

  • To synthesize and characterize twisted tolane derivatives (tolanophanes) using various tethers.
  • To explore how forced twisting affects the photophysical properties (absorption, emission) of tolanes.
  • To elucidate the mechanism behind observed phosphorescence in twisted tolane systems.

Main Methods:

  • Synthesis of tolanophanes with specific tether lengths to control torsion angles.
  • X-ray crystallography to determine solid-state torsion angles.
  • Spectroscopic analysis, including absorption, emission, and excitation spectra.
  • Low-temperature (77 K) emission spectroscopy in a rigid matrix.
  • Quantum chemical calculations (TD-DFT) to investigate electronic states and intersystem crossing (ISC).

Main Results:

  • Tethered tolanes exhibited tether-specific torsion angles in the solid state.
  • Twisted conformers showed blue-shifted absorption spectra.
  • Emission spectra were independent of torsion angle and identical across samples.
  • Unexpectedly long-lived phosphorescence was observed for twisted tolanes at 77 K.
  • Quantum chemical calculations identified favorable ISC pathways at specific singlet-triplet state crossings (S1/T6, S1/T7, S1/T(8,9), S1/T10).

Conclusions:

  • Forcing tolane backbones into twisted conformations significantly influences their photophysical behavior, particularly inducing phosphorescence.
  • The observed phosphorescence is attributed to efficient intersystem crossing facilitated by large spin-orbit coupling at specific singlet-triplet state crossings, as predicted by computational modeling.
  • Tethered tolanes provide a valuable platform for studying structure-property relationships in organic molecules.