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April 10, 2026The Journal of Organic Chemistry0 citations

Self-Sensitized Photooxidation in Extended Tetrathiafulvalenes

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ADAlexander L. O. DegnerASAmanda F. SmithDPDuccio Di Prima

Key Points

  • The research investigates how extended tetrathiafulvalenes affect singlet molecular oxygen sensitization in organic dyes.
  • Synthesis of novel 2,1,3-benzothiadiazole-based extended tetrathiafulvalenes
  • Assessment of their photophysical properties
  • Analysis of the relationship between dithiafulvene units and molecular singlet oxygen generation
  • Dithiafulvene units showed a clear link to reduced singlet oxygen generation
  • Photophysical analyses indicated that this reduction leads to increased stability
  • [2 + 2] cycloaddition reactions resulted from lower singlet oxygen levels

Abstract

Photostability of organic dyes is a critical challenge in the field of organic photovoltaics, as prevalent exposure to light and air can lead to degradation of the active ingredient. In our study, a series of novel 2,1,3-benzothiadiazole-based extended tetrathiafulvalenes was synthesized and assessed for their photophysical properties. Extended tetrathiafulvalenes are promising candidates for dyes in organic photovoltaics, yet the role that dithiafulvene plays in singlet molecular oxygen sensitization remains unclear. Photophysical analyses show a clear link between dithiafulvene units and a decreased generation of molecular singlet oxygen, which further results in a 2 + 2 cycloaddition reaction and cleavage of the said unit.

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Cite This Study

Degner et al. (2026) studied this question.

synapsesocial.com/papers/69d892886c1944d70ce03dfahttps://doi.org/10.1021/acs.joc.6c00358
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