Abstract
AbstractWe report on the chemical synthesis and characterization of free‐base A2B‐ and A3‐meso‐TIPS ethynyl corroles, which serve as a precursor for metalation with gallium(III)chloride and subsequent in‐situ sila Sonogashira cross‐coupling reaction. Under ambient conditions and with a common catalyst system the reaction with different aryliodides proved to be successful. Compared to the well‐known Ga(III)‐pyr‐5,10,15‐trispentafluorophenylcorrole complex, the emission wavelengths of such gallium(III) corroles complexes could be shifted bathochromically by up to ∼3100 cm−1 to the near‐infrared region (NIR). The described synthetic procedure establishes a facile way to obtain organic near‐infrared‐emitters based on gallium(III) meso‐aryl‐ethynyl corrole complexes.
Highlights
2H-corroles from a meso-ethynyl-3H-corroles paved the way for our study to synthesize free-base and metal meso-aryl-ethynyl corroles.[21,29]
Deprotection of the TIPS-group with TBAF led to deprotonation of the pyrrolic nitrogen atoms of the corrole macrocycles, which degrade over time.[22,40]
To circumvent this problem we decided to protect the inner core via metalation with gallium(III)
Summary
2H-corroles from a meso-ethynyl-3H-corroles paved the way for our study to synthesize free-base and metal meso-aryl-ethynyl corroles.[21,29]. We have synthesized free-base and gallium A2B- and A3-meso-TIPS ethynyl corroles and studied the photophysical effects of various aryl-ethynyl substituents at the meso-positions 5, 10, 15 of the highly fluorescent gallium A3and A2B-corroles. For this purpose, an automated microreactor system was used to couple gallium A2B- and A3-meso-TIPS ethynyl corroles with the according aryliodes under in-situ silaSonogashira conditions.[37,38,39]
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