Abstract
Arylsilyl substituted pyrene derivatives were synthesized via Suzuki-Miyaura and Hagihara-Sonogashira cross-coupling reactions with boronic acid-terminated and ethynyl-terminated tetraphenylsilane at the 1-, 3-, 6- and 8-positions. The spectroscopic properties of the dyes were investigated in various solvents and in films to assess the suitability of these compounds for optoelectronic applications. A triphenylsilylphenyl substituted pyrene was found to exhibit intense emission in the solid state with an absolute fluorescence quantum yield (ΦF) of 0.65. In contrast, the emission properties of a triphenylsilylphenyl(ethynyl) substituted pyrene were found to be somewhat weaker in the solid state (ΦF = 0.16) and solvent polarity dependent in solution. Magnetic circular dichroism (MCD) spectroscopy, cyclic voltammetry, and theoretical calculations have been used to analyze the structure-property relationships with Michl's perimeter model used as a conceptual framework for rationalizing the key trends.
Original language | English |
---|---|
Pages (from-to) | 771-778 |
Number of pages | 8 |
Journal | Dyes and Pigments |
Volume | 99 |
Issue number | 3 |
DOIs | |
Publication status | Published - 2013 Aug 27 |
Keywords
- Fluorescence
- Pigments
- Pyrene dyes MCD spectroscopy
- Solid-state emission
- TD-DFT calculations
ASJC Scopus subject areas
- Chemical Engineering(all)
- Process Chemistry and Technology