Session: Physical Organic Chemistry: Calculations, Mechanisms, Photochemistry & High-Energy Species:

Perylene diimides (PDIs) are a well-studied class of organic chromophores, with exceptional thermal and photochemical stability, tunable electron absorption spectra in the visible region, and high fluorescence quantum yields. Thus, due to their exceptional optical and electrical properties, PDIs have the potential to be utilized for a variety of applications spanning a number of disciplines. Herein, regioisomers of 1,6-, 1,7-, and 1,6,7-dodecylthio-N,N’-(2,4-diisopropylanaline)perylene diimide were successfully synthesized, isolated, and characterized via high resolution MS and ¹H NMR. Significant differences in the electronic absorption and emission spectra and excited state lifetimes were observed between the 1,6- and 1,7-Thio-PDI, but also with the tri-substituted 1,6,7-Thio-PDI. A solvochromatic study of the absorption and emission properties was performed and analyzed by the Lippert-Mataga approximation to evaluate the excited state dipole moment changes. Understanding the charge transfer characteristics between the various isomers will aid in the use of these materials in potential electrooptical applications.

Zhaorui Huang

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