Iptycene-Containing Azaacenes with Tunable Luminescence
Author(s)Schleper, Alexander Lennart; Voll, Constantin-Chri Alexander; Engelhart, Jens; Swager, Timothy M
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An optimized route toward iptycene-capped, p-dibromo-quinoxalinophenazine was developed, increasing the yield significantly from literature procedures. New iptycene-containing symmetrical azaacenes were synthesized from this intermediate using Suzuki–Miyaura cross-coupling, and their photophysical properties were evaluated. Tuning the substituents allows modulating emission wavelengths across the visible spectrum. Substitution with 3-methoxy-2-methylthiophene exhibits a quantum yield of 35%. The (triisopropylsilyl)acetylene product has a quantum yield of 38% and serves as a model compound for the synthesis of polymers based on this electrooptically active molecular motif. Keywords: N-heteroiptycene - Suzuki–Miyaura cross-coupling - Sonogashira coupling - pyrazinoquinoxaline - luminescence
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Thieme Publishing Group
Schleper, A., et al. “Iptycene-Containing Azaacenes with Tunable Luminescence.” Synlett, vol. 28, no. 20, Dec. 2017, pp. 2783–89.