Polyaromatic hydrocarbons (PAH) possessing both high quantum yields (F > 0.9) and good photostability (~ 10 years) are promising fluorophores for use in luminescent solar concentrator materials. In an effort to increase both solubility and alignability in liquid crystal and polymer matrices, perylene (perylene-3,4,9,10-tetracarboxylic dianhydride) and terrylene (terrylene-3,4,11,12-tetracarboxdiimide) based dyes were imidizized with diisopropylaniline derivatives synthesized via facile Sonagashira and hydrogenation conditions. Substitution at the para position with alkyl and alkyne tails of varying length lead to an increase in alignability by providing the dye with a more rod like structure, while the bulky 2,6-diisopropyl groups increased solubility by impeding intermolecular p-p stacking. In addition to the aforementioned properties, photostability, quantum yield, UV-vis and fluorescence data will be discussed.

Synthesis of alignable fluorophores for light harvesting in liquid crystal and polymeric waveguides

243rd National Meeting (2012)

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